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Quality Control of [ 123-08-0 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 123-08-0 ]

Product Citations Expand+

Nitrothiazole-Thiazolidinone Hybrids: Synthesis and in Vitro Antimicrobial Evaluation

Dylan Hart ; Lesetja J. Legoabe ; Omobolanle J. Jesumoroti , et al. Chem. Biodivers.,2022,19(11):e202200729. DOI: 10.1002/cbdv.202200729 PubMed ID: 36102043

Abstract: Herein we report the synthesis of novel compounds inspired by the antimicrobial activities of nitroazole and thiazolidin-4-one based compounds reported in the literature. Target compounds were investigated in?vitro for antitubercular, antibacterial, antifungal, and overt cell toxicity properties. All compounds exhibited potent antitubercular activity. Most compounds exhibited low micromolar activity against S. aureus and C. albicans with no overt cell toxicity against HEK-293 cells nor haemolysis against human red blood cells. Notably, compound 3b exhibited low to sub-micromolar activities against Mtb, MRSA, and C. albicans. 3b showed superior activity (0.25?μg/ml) against MRSA compared to vancomycin (1?μg/ml).

Purchased from AmBeed: 613-45-6 ; 121-66-4 ; 587-04-2 ; 104-87-0 ; 552-89-6 ; 456-48-4 ; 830-79-5 ; 555-16-8 ; 104-88-1 ; 591-31-1 ; 3132-99-8 ; 446-52-6 ; 459-57-4 ; 529-20-4 ; 6287-38-3 ; 123-08-0 ; 100-52-7 ; 349121-09-1 ; 89-98-5 ...More

Design, synthesis and evaluation of amino-3, 5-dicyanopyryridines and thieno [2, 3-b] pyridines as ligands of adenosine receptors

Nkomba, Gaofenngwe ; Terre' ; Blanche, Gisella , et al. Research Square,2022. DOI: 10.21203/rs.3.rs-1500396/v1 PubMed ID: 35634433

Abstract: Due to the implication of adenosine in seizure suppression, adenosine-based therapies such as adenosine receptor (AR) agonists have been investigated. This study aimed at investigating thieno[2,3 b]pyridine derivatives as non-nucleoside A1 agonists that could be used in pharmaco-resistant epilepsy (PRE). Compound 7c (thieno[2,3-b]pyridine derivative), displayed good binding a nity to the rA1 AR (Ki = 61.9 nM). This could be a breakthrough for further investigation of this heterocyclic scaffold as potential ligand. In silico evaluation of this compound raised bioavailability concerns but performed well on drug likeness tests. The effect of intramolecular cyclisation that occurs during synthesis of thieno[2,3 b]pyridines from the lead compounds, amino-3,5-dicyanopyridine derivatives ( 6a-s) in relation to AR binding was also evaluated. A signi cant loss of activity against rA1/rA2A ARs with cyclisation was revealed. Amino-3,5-dicyanopyridines exhibited greater a nity towards rA1 ARs (Ki

Keywords: Amino-3,5-dicyanopyryridines ; Thieno[2,3-b]pyridines ; Intramolecular cyclisation ; Adenosine A1/A2A receptors ; Epilepsy

Purchased from AmBeed: 123-08-0 ; 68470-59-7 ; 6515-58-8

Product Details of [ 123-08-0 ]

CAS No. :	123-08-0	MDL No. :	MFCD00006939
Formula :	C₇H₆O₂	Boiling Point :	-
Linear Structure Formula :	C₆H₄(OH)CHO	InChI Key :	RGHHSNMVTDWUBI-UHFFFAOYSA-N
M.W :	122.12	Pubchem ID :	126
Synonyms :	4-Formylphenol;p-Formylphenol;4-Hydroxybenzaldehyde	Chemical Name :	4-Hydroxybenzaldehyde

Calculated chemistry of [ 123-08-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	33.85
TPSA :	37.3 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.99
Log Po/w (XLOGP3) :	1.35
Log Po/w (WLOGP) :	1.2
Log Po/w (MLOGP) :	0.79
Log Po/w (SILICOS-IT) :	1.52
Consensus Log Po/w :	1.17

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.87
Solubility :	1.63 mg/ml ; 0.0133 mol/l
Class :	Very soluble
Log S (Ali) :	-1.74
Solubility :	2.25 mg/ml ; 0.0184 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.72
Solubility :	2.31 mg/ml ; 0.0189 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 123-08-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 123-08-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 123-08-0 ]
Downstream synthetic route of [ 123-08-0 ]

[ 123-08-0 ] Synthesis Path-Upstream 1~5

1
[ 123-08-0 ]
[ 133865-89-1 ]

Reference： [1] Patent: CN106565520, 2017, A,
[2] Patent: CN106220525, 2016, A,
[3] Patent: WO2007/147491, 2007, A1,
[4] Patent: WO2007/147491, 2007, A1,
[5] Patent: WO2007/147491, 2007, A1,

2
[ 100-39-0 ]
[ 123-08-0 ]
[ 371-40-4 ]
[ 70627-52-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: at 20℃; for 12 h; Stage #2: for 4 h; Reflux	100 ml of DMF, p-hydroxybenzaldehyde (12.2 g, 0.1 mol), potassium carbonate (16.6 g, 0.12 mol) were successively added to a 250 ml three-necked flask, Benzyl bromide (20.4 g, 0.12 mol) was added dropwise, Room temperature reaction for 12 hours, The reaction solution was poured into ice water, Solid precipitation,filter, Washed cake, The filter cake is dry. To give benzyl-protected p-hydroxybenzaldehyde (26.2 g)Yield 91percent. And then take another 250ml single neck round bottom flask, Followed by adding 100 ml of acetone, benzyl-protected p-hydroxybenzaldehyde (14.4 g, 0.05 mol), p-fluoroaniline (5.55 g, 0.05 mol) After the reaction was refluxed for 4 h, the reaction solution was cooled to 5 ° C to precipitate a solid, filter, The solid was washed with cold acetone, The solid was dried to give N-(4-fluorophenyl)-4-benzyloxybenzylideneamine (Compound IV) 14g, Yield 92percent.

Reference： [1] Patent: CN106397292, 2017, A, . Location in patent: Paragraph 0092; 0093
[2] Patent: WO2008/96372, 2008, A2, . Location in patent: Page/Page column 17

3
[ 123-08-0 ]
[ 70627-52-0 ]

Reference： [1] Patent: JP2016/147843, 2016, A,

4
[ 123-08-0 ]
[ 403648-76-0 ]

Reference： [1] Journal of Fluorine Chemistry, 2001, vol. 111, # 2, p. 153 - 160

5
[ 76-83-5 ]
[ 123-08-0 ]
[ 892112-24-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 6 h;	General procedure: The 4-hydroxybenzaldehyde 4 (0.8 g, 6.5 mmol) was reacted with 4-monometoxytriphenylmethyl (1.0 g, 3.2 mmol) in 10 mL of anhydrous DCM in the presence of DIEA (2.2 mL, 12.9 mmol). After 6 h at r.t., the reaction was quenched by dilution with DCM (100 mL), and the organic phase was washed three times with a solution of 0.1 M NaOH (3×100 mL). The organic phase was dried with MgSO₄, and then the solvent was removed under vacuum. The crude material was then purified on a column of silica gel (70 g) suspended in hexane/EtOAc 70:30 (v/v) with 1percent of TEA, leading to product 5 (1.05 g, 82percent). ¹H NMR (400 MHz, 25°C, δ, ppm in CDCl₃): δ 9.76 (s, 1H), 7.57–7.25 (complex signals, 14H), 6.86 (d, J=8.5 Hz, 2H), 6.82 (d, J=8.0 Hz, 2H), 3.77 (s, 3H). ¹³C NMR (100 MHz, 25°C, δ, ppm in CDCl₃): δ 190.7, 161.9, 158.7, 143.8, 134.9, 130.6, 130.2, 128.3, 127.8, 127.3, 120.3, 113.1, 91.1, 55.0. Product 5 (1.05 g, 2.66 mmol) was subsequently treated with 0.25 g of NaBH₄ (6.60 mmol) in THF (10 mL) for 6 h at r.t. The mixture was diluted with DCM (3×100 mL), and the organic phase was washed three times with water (100 mL). The organic phase was dried with MgSO₄, and then the solvent was removed under vacuum. The crude solid thus obtained was purified on a column of silica gel (70 g) suspended in hexane/EtOAc 60:40 (v/v) with 1percent of TEA. From the column was recovered 0.845 g of clean desired product 6 (2.13 mmol, 80percent). ¹H NMR (400 MHz, 25°C, δ, ppm in CDCl₃): δ 7.49 (d, J=6.0 Hz, 4H), 7.37–7.22 (complex signals, 8H), 6.98 (d, J=7.2 Hz, 2H), 6.79 (d, J=7.2 Hz, 2H), 6.70 (d, J=6.8 Hz, 2H), 4.45 (s, 2H), 3.75 (s, 3H). ¹³C NMR (100 MHz, 25°C, δ, ppm in CDCl₃): δ 158.4, 155.8, 144.5, 135.6, 133.3, 130.4, 128.6, 127.6, 127.4, 126.9, 120.6, 112.8, 90.0, 64.8, 55.0. Then, 0.40 g (1.01 mmol) of product 6 was reacted with N,N-diisopropyldichlorophosphoramidite (124 μL, 0.67 mmol) in the presence of DIEA (348 μL, 2.68 mmol) in DCM (7 mL). After 1.5 h, the reaction was quenched by dilution with DCM, and the organic phase was washed three times with cold water. The organic phase was dried with MgSO₄ and the solvent removed under vacuum. The material was purified with column chromatography of silica gel in hexane/EtOAc 85:15 (v/v) with 2percent of TEA. From the column was recovered 0.74 g of clean desired product (1, 87percent).

Reference： [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 10, p. 2979 - 2988
[2] Tetrahedron Letters, 2017, vol. 58, # 12, p. 1227 - 1229

[ 123-08-0 ] Synthesis Path-Downstream 1~20

1
[ 123-08-0 ]
[ 2314-36-5 ]

Yield	Reaction Conditions	Operation in experiment
55%	With sulfuryl dichloride; In chloroform;Inert atmosphere; Reflux;	Compound R53 (4.9 g, 40 mmol) was dissolved in 80 ml of dry chloroform, followed by argon gasProtected, heated to reflux, slowly added dropwise a solution of 20 ml of sulfonyl chloride (6.4 ml, 80 mmol) in chloroform, and then refluxed overnight. The reaction solution was spin-dried and purified on a silica gel column. Yield 4.2g (55percent).

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 2936 - 2941
[2]Patent: CN104341347,2018,B .Location in patent: Paragraph 0134; 0135
[3]Chemische Berichte,1904,vol. 37,p. 4033
[4]Chemische Berichte,1896,vol. 29,p. 2357

2
[ 84-67-3 ]
[ 151-50-8 ]
[ 123-08-0 ]
[ 139555-29-6 ]

Reference： [1]Journal of the Indian Chemical Society,1991,vol. 68,p. 464 - 465

3
[ 123-08-0 ]
/PXGAB₁₁₄--212/ [ No CAS ]
[ 61439-59-6 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 1223 - 1227

4
[ 123-08-0 ]
[ 17701-61-0 ]
[ 661480-83-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 48h;	To a solution of 4-hydroxybenzaldehyde (2.7 g), benzyl hydroxypivalate (4.7 g) and triphenylphosphine (6.4 g) in tetrahydrofuran (22 mL) was added diethyl azodicarboxylate (40% toluene solution, 11 mL), and the mixture was stirred at room temperature for 2 days. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 6/1 - 4/1) to give the title compound (0.97 g).1H-NMR (CDCl3) delta ppm: 1.36 (6H, s), 4.07 (2H, s), 5.15 (2H, s), 6.9-7.0 (2H, m), 7 . 2-7 . 35 (5H, m), 7.75-7.85 (2H, m), 9.89 (1H, s)

Reference： [1]Patent: EP1544208,2005,A1 .Location in patent: Page/Page column 43

5
N,N'-dicyclodicyclohexylcarbodiimide [ No CAS ]
[ 123-08-0 ]
[ 83883-26-5 ]
[ 175798-17-1 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In dichloromethane; water;	(a) 0.6 g of N,N'-dicyclodicyclohexylcarbodiimide is added at room temperature while stirring to a solution of 1.0 g of 4-[6-acryloyloxyhexyloxy]benzoic acid, 0.3 g of 4-hydroxybenzaldehyde and 0.04 g of 4-dimethylaminopyridine in 20 ml of dichloromethane. The reaction mixture is stirred at room temperature overnight, poured into 100 ml of water and then extracted three times with 50 ml of dichloromethane each time. The combined organic phases are washed twice with 100 ml of water each time, dried over magnesium sulphate, filtered and the filtrate is subsequently concentrated. Chromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 1:1) and two-fold recrystallization from ethanol of the fractions which are pure according to thin-layer chromatography gives 0.9 g of 4-(4-[6-acryloyloxyhexyloxy]phenylcarbonyloxy)benzaldehyde.

Reference： [1]Patent: US5593617,1997,A

6
[ 13220-33-2 ]
[ 123-08-0 ]
C₁₂H₁₅NO₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6467 - 6471

7
[ 558-42-9 ]
[ 123-08-0 ]
[ 1107662-91-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In N,N-dimethyl-formamide; for 24h;Reflux;	Example 2A4-(2-Hydroxy-2-methylpropoxy)benzaldehyde5.00 g (40.94 mmol) of 4-hydroxybenzaldehyde, 4.44 g (40.94 mmol) of 1-chloro-2-methyl-2-propanol and 6.08 g (57.32 mmol) of sodium carbonate are initially charged in 50 ml of dry DMF and stirred under reflux for 24 h.After cooling to RT, 20 ml of ethyl acetate and 20 ml of sat. aqueous sodium bicarbonate solution are added.The phases are separated, and the organic phase is dried over magnesium sulfate.After removal of the solvent, the residue is purified by column chromatography on silica gel 60 (mobile phase gradient: cyclohexane/ethyl acetate 5:1?1:1).This gives a reddish solid which is used without further purification for the subsequent step.Yield: 4.40 g (50percent of theory, 90percent purity)LC-MS (method 2): Rt=1.37 min; MS (ESIpos): m/z=195 [M+H]+.
	With sodium carbonate; In N,N-dimethyl-formamide; at 130℃;	5 g (40.94 mmol) of 4-hydroxybenzaldehyde were initially charged in 50 ml of DMF. 4.45 g (40.94 mmol) of 1-chloro-2-methylpropan-2-ol and 6.08 g (57.32 mmol) of sodium carbonate were added, and the mixture was then stirred at 130° C. overnight. Saturated aqueous sodium bicarbonate solution/ethyl acetate were added to the reaction mixture. The precipitate was filtered off and discarded. The two phases were separated from one another, and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated using a rotary evaporator. The residue was purified by column chromatography on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 5/1?1/2). Yield: 8.6 g (82percent of theory, 76percent pure) LC-MS (Method 4): Rt=1.17 min; MS (ESIpos): m/z=195 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta=9.87 (s, 1H), 7.86 (d, 2H), 7.12 (d, 2H), 4.70 (s, 1H), 3.84 (s, 2H), 1.21 (s, 6H).

Reference： [1]Patent: US2011/130377,2011,A1 .Location in patent: Page/Page column 19
[2]Patent: US2013/210795,2013,A1 .Location in patent: Paragraph 0402-0406

8
[ 123-08-0 ]
[ 22532-60-1 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 1,2-diphenyl-1,1,2,2-tetrahydroperoxyethane; hydrogen bromide; In water; acetonitrile; at 20℃; for 2.5h;	General procedure: To a solution of aniline/phenol (1 mmol) in CH3CN (4 mL), HBr and THPDPE (depending on the substrate as shown in Table 7) were added and the solution was stirred at room temperature. After the reaction was completed, Na2SO3 (3M, 1mL) was added to the stirring mixture followed by the addition of H2O (10 mL). The solution was stirred until the desired precipitates appeared. The products were filtered and more purification was carried out using silica- packed column chromatography (Hexane?EtOAc). All of the products were characterized on the basis of their melting points, IR, 1H NMR, and 13C NMR spectral analysis and compared with those reported
	With bromine; acetic acid; at 100℃; for 0.25h;	First, take into 100g of phenol in the reaction vessel, to which was added the CH 25 3I solution until completely dissolved phenol solution, then added thereto 10g of sodium hydroxide, stir, using a mixed gas of the container was sealed and pressurized to 0.8MPa, reaction at 40 1.5h, after the standing was right methylphenol; then on each apparatus with a stirrer, a condenser, a dropping funnel and a thermometer four flask at room temperature, poured into the above obtained methyl phenol, to which was added to the resulting methyl phenol mass 0.5 times CaO2And 0.4 times the magnesium oxide to elevate the temperature to 35 , stir quickly sealed container, in the 10s the pressure vessel as to the standard atmospheric pressure, the reaction after 45min, to obtain p-hydroxybenzaldehyde; subsequently obtained in the above hydroxybenzaldehyde and immediately added 150mL mass concentration of 37percent HAC solution and 120mL of bromine liquid, stir and stand for 15min, then placed in a blender, set the speed to 400r / min, the temperature is set to 100 , until the liquid container is less than 1/3 of its original volume, speed and stopping heating, cooled to room temperature, to give 2-bromo-hydroxybenzaldehyde; thereafter the resultant 2-bromo-hydroxybenzaldehyde was cooled to -3 after the negative pressure 1.5MPa added dropwise with stirring 120mL of nitroethane, dropping to 3 drops per second, after the completion of the dropwise addition the reaction was stirred at 2 2h, then increase normal temperature, and filtered to give 2- nitro-1- (2-bromo-4-hydroxy) propylene benzene; Next after filtration to give 2-nitro-1- (2-bromo-4-hydroxy) propylene benzene placed again after disinfection, means with a stirrer, a condenser, a dropping funnel and a thermometer, 4-neck flask, while adding 0.5g of Fe, heated to 105 deg.] C, then again in the form of added dropwise 60mL mass concentration of 40percent HCl solution, 3min the completion of the dropwise addition, stirring evenly, sealed reaction 2h, then cooled to room temperature, to obtain 2-bromo-4-hydroxyphenyl acetone; Finally, the 2-bromo-4-hydroxyphenyl acetone at a pressure of 0.6MPa, a temperature condition is 110 , was added 35mL of CH3OH solution and 50mL of PCl3Solution, and the pH was adjusted to 6.5, after mixing evenly, increasing the temperature to 115 deg.] C, reaction was continued for 2h, cooled, filtered and dried to give 2-methoxy-4-hydroxyphenyl acetone.This unique and novel method, during the operation without the environmental pollution, the reaction process easy, moderate, so that the finally obtained 2-methoxy-4-hydroxyphenyl acetone 7.4g, yield of 90percent.

Reference： [1]Tetrahedron,2018,vol. 74,p. 6584 - 6592
[2]Organic Letters,2011,vol. 13,p. 3686 - 3689
[3]Patent: CN105418399,2016,A .Location in patent: Paragraph 0005; 0012

9
[ 4876-10-2 ]
[ 123-08-0 ]
[ 1041095-99-1 ]

Reference： [1]Monatshefte fur Chemie,2012,vol. 143,p. 1075 - 1086

10
[ 57497-39-9 ]
[ 123-08-0 ]
[ 93376-44-4 ]

Yield	Reaction Conditions	Operation in experiment
35%	With sodium hydrogencarbonate; In ethanol; at 100℃; for 0.166667h;Microwave irradiation;	General procedure: A mixture of the corresponding hydroxy benzaldehyde (1 equiv), N-tert-buthyl hydroxylamine hydrochloride (1.1 equiv), and sodium bicarbonate (1.1 equiv) in absolute ethanol (5 mL/mmol) as solvent was heated under microwave irradiation until the carbonyl compound was not present or there was no progress in the reaction (checked by TLC). The solvent was removed in vacuo and the reaction mixture diluted with H2O and extracted with EtOAc. After the workup of the combined organic layers, the residue was purified by column chromatography (SiO2, mixtures of petroleum ether/EtOAc).

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 58,p. 44 - 49

11
[ 36062-04-1 ]
[ 123-08-0 ]
[ 57-13-6 ]
[ 1432038-15-7 ]

Yield	Reaction Conditions	Operation in experiment
37%		General procedure: To a solution of the corresponding aromatic aldehyde (0.27 mmol) in EtOH (0.5 mL) was added urea (0.54 mmol) and CuSO4·5H2O (0.054 mmol). The mixture was stirred at 80 °C for 15 minutes before tetrahydrocurcumin or tetrahydrodemethoxycurcumin (0.27 mmol) was added. The reaction mixture was continued stirring for 24 hours and quenched with water (2 mL). The solution was washed with water (10 mL) and extracted with EtOAc (415 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated under reduced pressure to afford crude product as a yellow brown oil. Purification was accomplished by column chromatography eluting with 60percent-75percent EtOAc/hexane to furnish compounds 8-17.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2880 - 2882

12
[ 123-08-0 ]
[ 71-36-3 ]
[ 94-26-8 ]

Yield	Reaction Conditions	Operation in experiment
61%		General procedure: B(C6F5)3 (1 mol %) was added to a stirringsolution of aldehyde (1 mmol) in MeOH (6 mL). After 15 min., 5.5 M TBHP indecane (3 mmol) was added slowly and reaction mixture was refluxed untilthe complete conversion of starting material (monitored by TLC). Aftercompletion of reaction, the methanol was evaporated in vacuo. Later, thereaction mixture was diluted with water (20 mL) and extracted with ethylacetate (3 15 mL). The organic layer was washed with cold saturated sodiumbicarbonate solution (2 20 mL) followed by brine. The organic layer wasdried over MgSO4 and concentrated under reduced pressure and products werepurified over silica gel column chromatography in ethyl acetate/hexane. Allcompounds were characterized and confirmed by comparison of their spectraldata and physical properties with reported literature.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 889 - 892

13
[ 123-08-0 ]
[ 13214-64-7 ]
(4Z)-2-(4-methoxyphenyl)-4-[(4-Hydroxyphenyl)methylidene]-1,3-oxazol-5(4H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With potassium acetate; acetic anhydride; at 100℃;Inert atmosphere;	General procedure: Aromatic aldehyde (1 equiv.) was added to the solution of hippuric acid (1 equiv.) and potassium acetate (1 equiv.) in acetic anhydride under stirring. The mixture was refluxed under argon for 2?4 h at 100 °C and then cooled for the product precipitation. The precipitate was filtered, washed by distilled water and ether and dried on air.

Reference： [1]Medicinal Chemistry Research,2016,vol. 25,p. 1239 - 1249

14
[ 78364-55-3 ]
[ 123-08-0 ]
C₁₄H₁₀FN₃OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 70 - 80℃; for 3h;	General procedure: The mixture of <strong>[78364-55-3]6-fluoro-2-hydrazinylbenzo[d]thiazole</strong> (2) (0.01 mol) and benzalde-hyde/substituted benzaldehyde (0.01 mol) was reuxed in ethanol (15 ml) at 70?80 °C for 3 h. The separated product obtained was ltered off, washed withdistilled water and recrystallized from methanol to give the correspondinghydrazone. The product obtained was further dissolved in acetic acid (20 ml) atroom temperature followed by the addition of sodium acetate (0.5 g). Bromine(2 mmol) in acetic acid (10 ml) was added dropwise to the reuxing reactionmixture. After 1 h, the mixture was poured onto crushed ice (100 g). The precipitateobtained was ltered off and crystallized from ethanol-dimethylformamide (1:1) togive crystals of (3a?3t).

Reference： [1]Research on Chemical Intermediates,2016,vol. 42,p. 8329 - 8344

15
[ 123-08-0 ]
[ 83883-26-5 ]
[ 175798-17-1 ]

Yield	Reaction Conditions	Operation in experiment
57 g	With dmap; diisopropyl-carbodiimide; In dichloromethane;Inert atmosphere;	Under a nitrogen atmosphere, 50.0 g of the compound represented by the formula (I-1-1), 20.9 g of the compound represented by the formula (I-1-2), N, N-dimethylaminopyridine And 300 mL of dichloromethane were added. 25.9 g of diisopropylcarbodiimide was added dropwise and stirredIt was. After usual work-up, purification was carried out by column chromatography and recrystallization to obtain 57.0 g of a compound represented by the formula (I-1-3).
4.3 g	With dmap; diisopropyl-carbodiimide; In dichloromethane; at 20℃;Cooling with ice; Inert atmosphere;	In a nitrogen atmosphere, 4.0 g of a compound represented by the formula (I-114-1), 1.7 g of a compound represented by the formula (I-114-2), 0.3 g of N,N-dimethylaminopyridine, and 30 mL of dichloromethane were put in a reactor. With cooling with ice, 2.1 g of diisopropylcarbodiimide was dropwise added thereto and stirred at room temperature. The precipitate was taken out through filtration, and the filtrate was washed with hydrochloric acid, water and salt solution. This was purified through column chromatography (silica gel) and recrystallization (dichloromethane/methanol) to give 4.3 g of a compound represented by the formula (I-114-3).

Reference： [1]Patent: JP2016/193869,2016,A .Location in patent: Paragraph 0099; 0100
[2]Patent: US2018/22716,2018,A1 .Location in patent: Paragraph 0289

16
[ 7474-78-4 ]
[ 123-08-0 ]
2-(4-hydroxyphenyl)-1H-benzimidazole-5-sulfonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium metabisulfite; In ethanol; water; for 24h;Reflux;	General procedure: To a solution of the appropriate 3,4-diaminobenzene derivative (1ad)(2 mmol) in ethanol (15 mL) 2.85 N aqueous solution of sodium metabisulphite (1.6 mL) and the appropriate substituted arylaldehyde(2 mmol) were added. The reaction mixture was heated at reflux for 24 h. The solvent was then evaporated under reduced pressure. The residue was added with HCl 1 N (10 mL), the formed precipitate was filtered off, washed with water (3×10 mL) and purified by crystallization from the adequate solvent to give the title compounds.Following the general procedure benzimidazoles 3 [19], 4 [20], 5 [21],7 [24], 6, 32 and 33 [15] were prepared and their analytical and spectral data are in agreement with those reported in literature.

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2017,vol. 32,p. 527 - 537
[2]Bioorganic Chemistry,2019

17
[ 54396-44-0 ]
[ 123-08-0 ]
[ 868-85-9 ]
dimethyl ((4-hydroxyphenyl)((2-methyl-3-(trifluoromethyl)phenyl)amino)methyl)phosphonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With chitosan; In neat (no solvent); at 75℃; for 0.0666667h;Microwave irradiation; Green chemistry;	General procedure: An equimolar mixture of <strong>[54396-44-0]2-methyl-3-(trifluoromethyl)aniline</strong> (0.351 g, 0.002 mol), corresponding aldehyde (0.002 mol), dimethyl phosphite (0.18 ml, 0.002 mol) and chitosan catalyst (10 molpercent) were taken in a reaction glass tube, degassed for 10 min and microwave irradiated at 180 W for 2 min at 60 °C. The progress of the reaction was monitored by TLC using petroleum ether and ethyl acetate (3:7) as solvent. After completion of the reaction, the mixture was diluted with ethyl acetate, washed with water (2 x 15 ml) followed by brine (1 x 10 ml), dried over Na2SO4 and evaporated to dryness. The crude mass was purified by column chromatography on silicagel (100-200 mesh) by using a 7:3 mixture of ethyl acetate in hexane to afford the pure alpha-aminophosphonates.

Reference： [1]Research on Chemical Intermediates,2017,vol. 43,p. 7087 - 7103

18
[ 123-08-0 ]
[ 4903-09-7 ]

Reference： [1]Patent: WO2009/158393,2009,A1

19
[ 123-08-0 ]
[ 13214-64-7 ]
C₁₇H₁₃NO₄ [ No CAS ]

Reference： [1]Bioorganic Chemistry,2019,vol. 82,p. 109 - 116

20
[ 123-08-0 ]
[ 61439-59-6 ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 12002 - 12005

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Isomers

Technical Information

? Acidity of Phenols ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Chan-Lam Coupling Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Fischer Indole Synthesis ? Grignard Reaction ? Halogenation of Phenols ? Hantzsch Dihydropyridine Synthesis ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Julia-Kocienski Olefination ? Knoevenagel Condensation ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mukaiyama Aldol Reaction ? Nozaki-Hiyama-Kishi Reaction ? Oxidation of Phenols ? Passerini Reaction ? Paternò-Büchi Reaction ? Pechmann Coumarin Synthesis ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reformatsky Reaction ? Reimer-Tiemann Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Stetter Reaction ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
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P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P230	Keep wetted
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P232	Protect from moisture.
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P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
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P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
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Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
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P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ 123-08-0 ] Synthesis Path-Upstream 1~5

[ 123-08-0 ] Synthesis Path-Downstream 1~20

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Aryls

Aldehydes

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[ 123-08-0 ]

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[ 123-08-0 ]