[ CAS No. 6609-56-9 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 6609-56-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 6609-56-9 ]

SDS Specification

Alternatived Products of [ 6609-56-9 ]

Product Details of [ 6609-56-9 ]

CAS No. :	6609-56-9	MDL No. :	MFCD00001783
Formula :	C₈H₇NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FSTPMFASNVISBU-UHFFFAOYSA-N
M.W :	133.15	Pubchem ID :	81086
Synonyms :

Calculated chemistry of [ 6609-56-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	37.65
TPSA :	33.02 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.82
Log Po/w (XLOGP3) :	1.55
Log Po/w (WLOGP) :	1.57
Log Po/w (MLOGP) :	1.12
Log Po/w (SILICOS-IT) :	1.8
Consensus Log Po/w :	1.57

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.02
Solubility :	1.27 mg/ml ; 0.00955 mol/l
Class :	Soluble
Log S (Ali) :	-1.85
Solubility :	1.87 mg/ml ; 0.014 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.58
Solubility :	0.353 mg/ml ; 0.00265 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.21

Safety of [ 6609-56-9 ]

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 [ 6609-56-9 ]

* 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 [ 6609-56-9 ]
Downstream synthetic route of [ 6609-56-9 ]

[ 6609-56-9 ] Synthesis Path-Upstream 1~1

1
[ 6609-56-9 ]
[ 42365-52-6 ]

Reference： [1] Journal of the American Chemical Society, 2016, vol. 138, # 28, p. 8781 - 8788
[2] European Journal of Organic Chemistry, 2015, vol. 2015, # 27, p. 5944 - 5948
[3] Catalysis Science and Technology, 2018, vol. 8, # 2, p. 499 - 507

[ 6609-56-9 ] Synthesis Path-Downstream 1~14

1
[ 6609-56-9 ]
[ 6134-53-8 ]
[ 5385-31-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1966,vol. 39,p. 401 - 402

2
[ 6609-56-9 ]
[ 2439-77-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With lithium hexamethyldisilazane; In diethyl ether; at 0 - 20℃; for 48.0833 - 72.0833h;	At 00C anhydrous ether was introduced to flask under Ar, LiHMDS (94 ml, 93.9 mmol) was then introduced and stirred for 5 mins. <strong>[6609-56-9]2-methoxy-benzonitrile</strong> (5g, 37.6 mmol) was added and the mixture was stirred at room temperature for 2-3 days. Upon completion of the reaction solvent was removed and 200 mL cold 1N HCI was added and stirred. The aqueous layer was extracted with Et2O, then adjust the pH was adjusted by 6N NaOH to 13. Extraction with CH2CI2, dried over Na2SO4 and filtered. Upon concentration the above benzamidine compound was obtained in 91% yield.
82%	With cobalt(II) chloride hexahydrate; oxygen; ethylenediamine; zinc; In neat (no solvent); at 120℃; under 3800.26 Torr; for 12h;Autoclave;	General procedure: The reaction was carried out in a 100-mL stainless steel autoclave. Phenylcyanide (0.10 g, 1.00 mmol) was added to a mixture of ethylenediamine (0.12 g, 2.00 mmol), CoCl26H2O (0.24 g, 1.00 mmol) and Zn (0.07 g, 1.00 mmol) and the vessel was placed in an autoclave. For some of the reactions that were carried out in solvent, 5 mL of solvent was also added. The autoclave was pressurized to 5.00 atm with O2. The mixture was stirred in a preheated oil bath at 120 C for 12 h. Then, the reaction mixture was cooled to room temperature and the product was purified by column chromatography on silica gel using n-hexane:CH2Cl2 (1:1) to give the benzamide(88 % yield).
61%	With C12H24O16Ru3*2H2O; In water; at 110℃; for 4h;Schlenk technique; Inert atmosphere; Autoclave;Catalytic behavior;	General procedure: Hydration reactions were carried out in Schlenk tube under N2atmosphere. The reaction mixture was prepared dissolving 5 mg(6.5 lmol) of catalyst 2 in 3 mL of H2O. The mixture was degassedand 1.5 mmol of corresponding acetonitrile substrate was addedwith micropipette to stirred solution. The reaction was allowedfor heating at 110 C using oil bath or microwave-assisted heating.The isomerization reactions of allylic alcohols were conductedSchlenk tube under N2 atmosphere. The reaction mixture wasprepared dissolving 3 mg (3.9 lmol) of catalyst 2 in 2 mL ofappropriate solvent (DMF, EtOH or H2O). The mixture wasdegassed and 1 mmol of corresponding allylic alcohol substratewas added with micropipette to stirred solution. The reactionwas allowed for heating using oil bath.The reaction solutions were analyzed by regular sampling usingGC/FID (Hewlett Packard) equipped with Beta DEX 120(30 m 0.25 mm 0.25 lm) 30 m long column. The degrees ofconversion were calculated on the basis of the ratio of areas ofthe substrate material and the products determined from correspondingchromatograms. The optimization of chromatographicmethods and the calibration procedures for detection of productsas well as substrates were realized by injection of authenticcommercial samples.

50%	With copper(l) iodide; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In nitromethane; water; at 20 - 100℃; for 2h;	To a nitromethane (0.1 mL) solution of 4-methoxybenzonitrile (1f) (30 mg, 0.225 mmol) were addedH2O (1.0 mL), DBU (69 mg, 0.436 mmol), copper (I) iodide (9 mg, 0.0451 mmol), cesium (I)carbonate (37 mg, 0.113 mmol) at room temperature. The reaction mixture was heated at 100 C for2 h and then poured into water (50 mL). The organic layer was separated and the aqueous layer wasextracted with AcOEt. The combined organic layer was dried over MgSO4. The solvent wasremoved under reduced pressure. The residue was purified by preparative TLC on silica gel elutingwith AcOEt-n-hexane (1:1) to give 2-methoxybenzamide (2f)S5 (17 mg, 50%) as pale yellow powders.mp 123-125 C,
92%Chromat.		General procedure: 0.6 mmol benzonitrile and 0.6 mmol DMSO were solved in 3 mL EtOH and pumped into inlet A, 50 μL 1 M NaOH (aq) solved in 1 mL EtOH and pumped into inlet B, 30% H2O2 (aq) was solved in 7 mL ethanol and pumped into inlet C (flow rate A: B: C = 1.54 μl/min:0.46 μl/min:0.3 μl/min for a 400s residence time). The whole system was maintained on 25 C. The flow system was equilibrated for 30 min, then the product stream was quenched and collected in a glass vessel with saturated aqueous NaHSO3 in it for 2 h. After being filtered, 5.0 ml of this solution was injected to the HPLC instrument for analysis. The conversion of the reaction was determined by relative area percentage of nitriles and corresponding amides. Conversion = Area (benzamide)/[Area (benzamide) + Area (benzonitrile)].
	With 5% Pd/CeO2; In water; at 140℃; for 18h;	Add 100mg Pd/CeO2 in 6g water (Pd load mass percentage: 5.0%,The mass percentage of the entire catalytic material in the mixture: 1.7%), 60 mg <strong>[6609-56-9]o-methoxybenzonitrile</strong> (mass percentage in the mixture: 1%), mixed uniformly; reacted at 140C for 18 hours,The conversion rate of <strong>[6609-56-9]o-methoxybenzonitrile</strong> is >99.0%,The corresponding selectivity of o-methoxybenzamide is >99.0%
	With manganese(IV) oxide; iron(III) oxide; cobalt(II,III) oxide; In tert-Amyl alcohol; water; at 80℃; for 24h;	To 6 g of tert-amyl alcohol, 100 mg of ferric oxide, 100 mg of tricobalt tetraoxide and 100 mg of manganese dioxide (mass percentage in the mixture: 4.6%), 60 mg <strong>[6609-56-9]o-methoxybenzonitrile</strong> (mass percentage in the mixture: 0.91% ), 200uL water (mass percentage in the mixture: 3.0%), mix well; react at 80C for 24 hours, the conversion rate of <strong>[6609-56-9]o-methoxybenzonitrile</strong> is 89.5%, the corresponding selectivity of o-methoxybenzamide is 99.0%.

Reference： [1]RSC Advances,2014,vol. 4,p. 1102 - 1106
[2]Organic Letters,2014,vol. 16,p. 1060 - 1063
[3]Patent: WO2007/62370,2007,A2 .Location in patent: Page/Page column 136
[4]Tetrahedron,1989,vol. 45,p. 3299 - 3306
[5]Journal of the American Chemical Society,2012,vol. 134,p. 6425 - 6433
[6]Research on Chemical Intermediates,2015,vol. 41,p. 5071 - 5078
[7]Organometallics,2011,vol. 30,p. 5442 - 5451
[8]Chemistry - A European Journal,2009,vol. 15,p. 8695 - 8697
[9]Inorganica Chimica Acta,2017,vol. 454,p. 107 - 116
[10]Organic Letters,2018,vol. 20,p. 1130 - 1133
[11]Synlett,2018,vol. 29,p. 2061 - 2065
[12]European Journal of Organic Chemistry,2017,vol. 2017,p. 1870 - 1875
[13]Journal of Medicinal Chemistry,2009,vol. 52,p. 5295 - 5298
[14]Tetrahedron,2018,vol. 74,p. 1527 - 1532
[15]Patent: CN111153825,2020,A .Location in patent: Paragraph 0122; 0123
[16]Patent: CN111153824,2020,A .Location in patent: Paragraph 0112-0113

3
[ 6609-56-9 ]
[ 771-28-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydroxylamine; In ethanol; water; at 20 - 55℃; for 40h;	Hydroxylamine (Fluka 55458; 50% in water; 11.28 ml 187.76 mmol; 5 eq.) was added to a solution of 2-methoxybenzonitrile (Alrich 231231 ; 4.59 ml 37.55 mmol; 1 eq.) in EtOH (50 ml_) and the resulting mixture was stirred at room temperature for 16 hours then at 55C for 24 hours. The solvent was then evaporated and the resulting colourless oil was further dried under high vaccum to give a white solid. The latter was triturated in n-hexane, filtered and dried to afford the title compound (6.29 g, quantitative) as a white solid. HPLC (Method A) : Rt 0.96 min (purity 99.2%).
73%	With hydroxylamine hydrochloride; sodium hydrogencarbonate; In ethanol; for 6h;Reflux;	General procedure: To a stirred suspension of nitrile (30 mmol) and hydroxylaminehydrochloride (3.13 g, 45 mmol) in EtOH (50 mL) a NaHCO3 (3.78 g,45 mmol)was added. The reaction mixturewas stirred under refluxfor 6 h. After the reaction had completed, the reaction mixture wasconcentrated under reduced pressure, and the residue was dilutedwith cold water (80 mL). The resulting precipitate was filtered off,washed with cold water (20 mL) and dried in air at roomtemperature.
63%	With hydroxylamine hydrochloride; potassium carbonate; In methanol; for 6h;Reflux;	General procedure: A 1.3 g of a solution of 4-chorobenzonitrile (16v, 9.69 mmol, 1 equivalent) was dissolved in 50 mL of methanol. To this 2 g of K2CO3 (14.53 mmol, 1.5 equiv) was added and mixed properly. The reaction mixture was cooled at 0 C, and 1.35 g of hydroxylamine hydrochloride (19.38 mmol, 2 equiv) was added in portion-wise. After completion of the addition, it was refluxed for 6 hr.Then evaporated the solvent and excess of water was added to afford the precipitate of the desired product which was filtered and dried.

50%

With hydroxylamine hydrochloride; sodium carbonate; In water; at 20℃;

General procedure: Na2CO3 (3.61 g, 34 mmol) was dissolved in water (83 mL), and NH2OHxHCl (4.30 g, 61.4 mmol) was slowly added. After complete removing of CO2 appropriate nitrile (19 mmol) was added and mixture was stirred at room temperature for several days. Solvents were evaporated under reduced pressure to final volume of 50 mL. Obtained solution was extracted with ethylacetate (2 x 50 mL) and dried over Na2SO4. The solvent was removed at reduced pressure, to give the raw product that was finally purified by crystallization in ethyl acetate or by chromatography on SiO2, eluting with hexane/ethyl acetate (yields 20-50 %).

Reference： [1]Patent: WO2009/43890,2009,A1 .Location in patent: Page/Page column 53
[2]European Journal of Medicinal Chemistry,2019,vol. 164,p. 92 - 105
[3]Bioorganic Chemistry,2020,vol. 100
[4]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5936 - 5940
[5]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 819 - 821
[6]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 601 - 615
[7]Journal of Medicinal Chemistry,2012,vol. 55,p. 68 - 83
[8]Organic Process Research and Development,2012,vol. 16,p. 1717 - 1726
[9]ChemMedChem,2019,vol. 14,p. 1257 - 1270

4
[ 72371-46-1 ]
[ 6609-56-9 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 898 - 901

5
[ 578-57-4 ]
K₄[Fe(CN)6] [ No CAS ]
[ 6609-56-9 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 2585 - 2588
[2]Journal of Chemical Research,2007,p. 484 - 485

6
[ 5419-55-6 ]
[ 6609-56-9 ]
[ 126-30-7 ]
[ 883899-02-3 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 2518 - 2520
[2]Organic Letters,2013,vol. 15,p. 2742 - 2745

7
[ 766-51-8 ]
potassium ferrocyanide [ No CAS ]
[ 6609-56-9 ]

Reference： [1]Synlett,2007,p. 543 - 546

8
[ 6609-56-9 ]
[ 771-28-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium hydroxide; hydroxyamino hydrochloride; In ethanol; at 20℃; for 12h;Heating / reflux;	Add potassium hydroxide (30.3 g, 225 mmol) to a solution of 2- methoxybenzonitrile (25.0 g, 187 mmol) and hydroxylamine hydrochloride (15.77 g, 225 mmol) in ethanol (500 mL) at room temperature under nitrogen and heat the mixture at reflux for 12 hours. Remove the solvent under reduced pressure, triturate the residue with ethyl acetate/hexanes (1: 9,300 mL) and collect by vacuum filtration to provide N hydroxy-2-methoxybenzamidine (24.0 g, 91%).
	With hydroxyamino hydrochloride; Sodium hydrogenocarbonate; In methanol; at 20 - 80℃; for 48h;	General procedure: General Method A for the synthesis of hydroxyamidines (A-4)To a solution of nitrile-derivative (1.0 eq.) in MeOH (0.5 M), hydroxylamine HCI (1.1 to 3.0 eq.)and NaHCO3 (1.1 to 3.0 eq.) was added at rt. The resulting suspension was stirred at a giventemperature and time (see Table 5). The mixture was concentrated in vacuo, then EtOAc wasadded to the remaining residue and the org. layer was washed with brine (lx), dried (MgSO4), filtered and concentrated to yield hydroxyamidine A-4. Listed in Table 5 below are hydroxylamidines of type A-4, prepared from either commercially available nitrile-derivates or synthesized according to described methods.
2.8 g	With hydroxyamino hydrochloride; triethylamine; In ethanol; lithium hydroxide monohydrate; at 70℃; for 15h;	To a stirred solution of 2-methoxybenzonitrile (2.0 g, 15.0 mmol, 1 .83 mL) in ethanol (20 mL) were added hydroxylamine hydrochloride (2.09 g, 30.0 mmol), triethylamine (3.04 g, 30.0 mmol, 4.16 mL), and water (2 mL), then the mixture was heated to 70 00 for 1 5h. The mixture was cooled and quenched with water (20 mL), extracted with dichloromethane (30 mL x 3), and the combined organicphases were washed with water (20 mL), saturated aqueous sodium chloride solution (20 mL), dried overanhydrous sodium sulfate, filtered, and concentrated to give N-hydroxy-2-methoxybenzimidamide (2.80 g)as a light green solid, which was used in next step directly. 1H NMR (400 MHz, Methanol-d4) O 7.47 -7.30 (m, 2H), 7.06 (d, J8.4 Hz, 1H), 6.95 (t, J7.5 Hz, 1H), 3.86 (s, 3H).

Reference： [1]Patent: WO2005/19184,2005,A1 .Location in patent: Page/Page column 29
[2]Patent: WO2014/141065,2014,A1 .Location in patent: Page/Page column 46; 47
[3]Organic and Biomolecular Chemistry,2014,vol. 12,p. 8036 - 8047
[4]Patent: WO2018/81167,2018,A1 .Location in patent: Page/Page column 107; 108
[5]Journal of Medicinal Chemistry,2022,vol. 65,p. 5449 - 5461

9
[ 529-28-2 ]
K₄[Fe(CN)6] [ No CAS ]
[ 6609-56-9 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 4693 - 4694

10
[ 6609-56-9 ]
[ 100-46-9 ]
[ 1039764-24-3 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 7; N-[4-Hydroxy-2-[2-(methyloxy)phenyl]-6-oxo-1-(phenylmethyl)-1,6-dihydro-5-pyrimidinyl]carbonyl}glycine; 7a) 6-Hydroxy-2-[2-(methyloxy)phenyl]-3-(phenylmethyl)-4(3H)-pyrimidinone; A 1 M solution of dimethylaluminium chloride in hexane (5.50 mL, 5.50 mmol) was added dropwise to a stirred solution of benzylamine (0.536 g, 5.00 mmol) in toluene (20 mL) under nitrogen. After stirring at ambient temperature for 20 min, 2-methoxybenzonitrile (1.33 g, 10.0 mmol) was added and the mixture refluxed for 18 h under nitrogen. After cooling, 1 M aqueous sodium hydroxide (40 mL) was added and the mixture concentrated under reduced pressure to remove the organic solvents, then extracted with ether. The extracts were dried (K2CO3, Na2SO4) and evaporated under reduced pressure to leave the crude amidine (1.12 g). A mixture of the crude amidine (0.268 g), diethyl malonate (0.359 g, 2.24 mmol), sodium methoxide in methanol (0.513 mL of a 4.37 M solution, 2.24 mmol) and 2-methoxyethanol (5 mL) was refluxed under nitrogen for 18 h, then cooled and diluted with water (20 mL). 6 M aqueous hydrochloric acid (2 mL) was added, the mixture stirred 0.5 h, and the precipitate filtered, washed with water and dried to give the title compound (0.283 g, 76%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.64 (s, 3 H) 4.69 (d, J=15.41 Hz, 1 H) 5.13 (d, J=15.66 Hz, 1 H) 5.47 (s, 1 H) 6.79-6.87 (m, 2 H) 6.95 (t, J=7.45 Hz, 1 H) 7.11 (d, J=8.34 Hz, 1 H) 7.14-7.23 (m, 4 H) 7.42-7.50 (m, 1 H) 11.63 (br. s., 1 H).

Reference： [1]Patent: US2008/171756,2008,A1 .Location in patent: Page/Page column 11

11
[ 1126528-26-4 ]
K₄[Fe(CN)6] [ No CAS ]
[ 6609-56-9 ]

Reference： [1]Australian Journal of Chemistry,2008,vol. 61,p. 581 - 584

12
[ 6609-56-9 ]
[ 144649-99-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With N-Bromosuccinimide; iodine; In acetonitrile; for 12h;Darkness;	General procedure: To a reaction tube charged with NBS (1.5 equiv, 0.3 mmol), catalyst (10 molpercent, 0.02 mmol) and CH3CN (1.0 mL),was added para-chloroanisole 1a (0.2 mmol). After being stirred at room temperature for 12 h in dark, the reaction was quenched by saturated aq. solution of Na2S2O3 (2 mL). The resulting mixture was extracted by ethyl acetate (3 5 mL). The combined organic extracts were washed by brine (10 mL), dried over Na2SO4 and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and the residuewas purified by flash chromatography on a silica gel column with petroleum ether/dichloromethane (5:1) as the eluent to give 4.3.1. 2-Bromo-4-chloroanisole (2a)
71%	With bromine; In chloroform; for 29h;Reflux;	Example 34 5-Bromo-2-(methyloxy)benzonitrile Br2 (13.7 g, 86.0 mmol) in CHCl3 (20 mL) was added to a solution of 2-(methyloxy)benzonitrile (10.9 g, 81.9 mmol) in CHCl3 (50 mL). The mixture was refluxed for 29 h. The reaction was allowed to cool to room temperature, and washed with saturated sodium bisulfite (50 mL), and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate. Evaporation of the solvent afforded 5-bromo-2-(methyloxy)benzonitrile (12.4 g, 71percent).
71%	With bromine; In chloroform; for 29h;Reflux;	Example 34 5-Bromo-2-(methyloxy)benzonitrile Bromine (13.7 g, 86.0 mmol) in CHCl3 (20 mL) was added to a solution of 2-(methyloxy)benzonitrile (10.9 g, 81.9 mmol) in CHCl3 (50 mL). The mixture was refluxed for 29 h. The reaction was allowed to cool to room temperature, and washed with saturated sodium bisulfite (50 mL), and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate. Evaporation of the solvent afforded 5-bromo-2-(methyloxy)benzonitrile (12.4 g, 71percent).

71%	With bromine; In chloroform; for 29h;Heating;	Example 37 5-Bromo-2-(methyloxy)benzonitrile Bromine (13.7 g, 86.0 mmol) in CHCl3 (20 mL) was added to the solution of 2-(methyloxy)benzonitrile (10.9 g, 81.9 mmol) in CHCl3 (50 mL). The mixture was refluxed for 29 h. The reaction was allowed to cool to room temperature, and washed with saturated sodium bisulfite (50 mL), and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate. Evaporation of the solvent afforded 5-bromo-2-(methyloxy)benzonitrile (12.4 g, 71percent).
71%	With bromine; In chloroform; for 29h;Reflux;	Example 34 5-Bromo-2-(methyloxy)benzonitrile <n="134"/>Br2 (13.7 g, 86.0 mmol) in CHCl3 (20 mL) was added to a solution of 2-(methyloxy)benzonitrile (10.9 g, 81.9 mmol) in CHCl3 (50 mL). The mixture was refluxed for 29 h. The reaction was allowed to cool to room temperature, and washed with saturated sodium bisulfite (50 mL), and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate. Evaporation of the solvent afforded 5-bromo-2-(methyloxy)benzonitrile (12.4 g, 71percent).

Reference： [1]Tetrahedron,2017,vol. 73,p. 7105 - 7114
[2]Patent: US2009/203657,2009,A1 .Location in patent: Page/Page column 51
[3]Patent: US2009/203677,2009,A1 .Location in patent: Page/Page column 54
[4]Patent: US2009/197871,2009,A1 .Location in patent: Page/Page column 53-54
[5]Patent: WO2009/100169,2009,A1 .Location in patent: Page/Page column 132-133

13
[ 67-56-1 ]
[ 6476-32-0 ]
[ 6609-56-9 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 4267 - 4272

14
[ 67-56-1 ]
[ 6609-57-0 ]
[ 6609-56-9 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 4267 - 4272

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Technical Information

? Benzylic Oxidation ? Birch Reduction ? Blaise Reaction ? Blanc Chloromethylation ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Friedel-Crafts Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Nomenclature of Ethers ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Preparation of Ethers ? Reactions of Benzene and Substituted Benzenes ? Reactions of Ethers ? Ritter Reaction ? Thorpe-Ziegler Reaction ? Vilsmeier-Haack Reaction

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Precautionary Statements-General
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.
P202	Do not handle until all safety precautions have been read and understood.
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.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
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.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
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.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
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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[ CAS No. 6609-56-9 ] {[proInfo.proName]}

Quality Control of [ 6609-56-9 ]

Related Doc. of [ 6609-56-9 ]

Product Details of [ 6609-56-9 ]

Calculated chemistry of [ 6609-56-9 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 6609-56-9 ]

Application In Synthesis of [ 6609-56-9 ]

[ 6609-56-9 ] Synthesis Path-Upstream 1~1

[ 6609-56-9 ] Synthesis Path-Downstream 1~14

Technical Information

Related Functional Groups of [ 6609-56-9 ]

Aryls

Ethers

Nitriles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 6609-56-9 ]