[ CAS No. 71597-85-8 ] {[proInfo.proName]}

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Quality Control of [ 71597-85-8 ]

COA NMR CNMR HPLC LC-MS

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Product Citations Expand+

Dioxin-Linked Covalent Organic Framework-Supported Palladium Complex for Rapid Room-Temperature Suzuki-Miyaura Coupling Reaction

Campbell, Allea ; Alsudairy, Ziad ; Dun, Chaochao , et al. Crystals,2023,13(8):1268. DOI: 10.3390/cryst13081268

Abstract: Covalent organic framework (COF)-supported palladium catalysts have garnered enormous attention for cross-coupling reactions. However, the limited linkage types in COF hosts and their suboptimal catalytic performance have hindered their widespread implementation. Herein, we present the first study immobilizing palladium acetate onto a dioxin-linked COF (Pd/COF-318) through a facile solution impregnation approach. By virtue of its permanent porosity, accessible Pd sites arranged in periodic skeletons, and framework robustness, the resultant Pd/COF-318 exhibits exceptionally high activity and broad substrate scope for the Suzuki-Miyaura coupling reaction between aryl bromides and arylboronic acids at room temperature within an hour, rendering it among the most effective Pd/COF catalysts for Suzuki-Miyaura coupling reactions to date. Moreover, Pd/COF-318 demonstrates excellent recyclability, retaining high activity over five cycles without significant deactivation. The leaching test confirms the heterogeneity of the catalyst. This work uncovers the vast potential of dioxin-linked COFs as catalyst supports for highly active, selective, and durable organometallic catalysis.

Keywords: covalent organic framework (COF) ; dioxin-linked COF ; Pd(II) immobilization ; Suzuki-Miyaura coupling

Purchased from AmBeed: 24067-17-2 ; 98-80-6 ; 3375-31-3 ; 71597-85-8 ; 4877-80-9 ; 99768-12-4

Versatile Nanoporous Organic Polymer Catalyst for the Size- Selective Suzuki-Miyaura Coupling Reaction

Guo, Sheng ; Wu, Yifan ; Luo, Shao-Xiong Lennon , et al. ACS Appl. Nano Mater.,2022,5(12):18603-18611. DOI: 10.1021/acsanm.2c04393

Abstract: Heterogenous catalysts with confined nanoporous catalytic sites are shown to have high activity and size selectivity. A solution-processable nanoporous organic polymer (1-BPy-Pd) catalyst displays high catalytic performance (TON > 200K) in the heterogeneous Suzuki–Miyaura coupling (SMC) reaction and can be used for the preparation of the intermediates in the synthesis of pharmaceutical agents. In comparison to the homogeneous catalyst analogue (2,2′-BPy)PdCl2, the heterogenous system offers size-dependent catalytic activity when bulkier substrates are used. Furthermore, the catalyst can be used to create catalytic impellers that simplify its use and recovery. We found that this system also works for applications in heterogenous Heck and nitroarenes reduction reactions. The metal-binding nanoporous polymer reported here represents a versatile platform for size-selective heterogeneous and recyclable catalysts.

Keywords: nanoporous organic polymer ; heterogeneous catalyst ; Suzuki?Miyaura coupling reaction ; size-selective reaction ; catalyst processing

Purchased from AmBeed: 128796-39-4 ; class="">10365-98-7 ; class="">98-80-6 ; class="">556-96-7 ; class="">171663-13-1 ; class="">71597-85-8 ; class="">402-43-7 ; class="">2042-37-7 ; class="">22385-77-9 ; class="">16419-60-6 ; class="">15862-18-7 ; class="">87199-15-3 ; class="">171408-84-7 ; class="">643-58-3 ; class="span_more span_less">591-50-4 ; class="span_more span_less">76911-73-4 ; class="span_more span_less">398-36-7 ; class="span_more span_less">14871-92-2 ; class="span_more span_less">5720-07-0 ; class="span_more span_less">945976-76-1 ; class="span_more span_less">366-18-7 ; class="span_more span_less">2920-38-9 ; class="span_more span_less">623-00-7 ; class="span_more span_less">24973-49-7 ; class="span_more span_less">588-59-0 ; class="span_more span_less">128796-39-4 ; class="span_more span_less">5723-93-3 ; class="span_more span_less">17057-88-4 ; class="span_more span_less">126485-55-0 class="keywords_more email-color more_span" onclick="change_span_more(this)">...More

Synthesis and biological evaluation of selected 7H-pyrrolo[2,3-d]pyrimidine derivatives as novel CDK9/CyclinT and Haspin inhibitors

Pieterse, Lianie ; Beteck, Richard M. ; Baratte, Blandine , et al. Chem.-Biol. Interac.,2021,349,109643. DOI: 10.1016/j.cbi.2021.109643 PubMed ID: 34508710

Abstract: Protein kinases, including CDK9/CyclinT and Haspin, are regarded as potential drug targets in cancer therapy. Findings from a previous study suggested 7-azaindole as a privileged scaffold for producing inhibitors of CDK9/CyclinT and Haspin. Inspired by these findings, the current study synthesized and evaluated thirteen (13) C6-substituted 7-azaindole and twenty (20) C4-substituted structurally related 7H-pyrrolo[2,3-d]pyrimidine derivatives against a panel of protein kinases, including CDK9/CyclinT and Haspin. Eleven of the 7H-pyrrolo[2,3-d]pyrimidine derivatives exhibited activity toward CDK9/CyclinT, while 4 of compounds had activity against Haspin. The best CDK9/CyclinT (IC50 of 0.38 μM) and Haspin (IC50 of 0.11 μM) activities were achieved by compounds 7d and 7f, resp. Hence, these compounds may be valuable starting points for development of new anti-cancer drugs.

Keywords: 7-Deazapurine ; Anticancer ; CDK9/CylinT ; Haspin ; Protein kinase

Purchased from AmBeed: 98437-24-2 ; 71597-85-8 ; 3680-69-1 ; 6165-68-0 ; 51067-38-0 ; 87199-18-6

Product Details of [ 71597-85-8 ]

CAS No. :	71597-85-8	MDL No. :	MFCD01074628
Formula :	C₆H₇BO₃	Boiling Point :	No data available
Linear Structure Formula :	(HO)C₆H₄B(OH)₂	InChI Key :	COIQUVGFTILYGA-UHFFFAOYSA-N
M.W :	137.93	Pubchem ID :	2734360
Synonyms :

Calculated chemistry of [ 71597-85-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	3.0
Molar Refractivity :	38.29
TPSA :	60.69 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.81 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.47
Log Po/w (WLOGP) :	-0.93
Log Po/w (MLOGP) :	-0.36
Log Po/w (SILICOS-IT) :	-1.2
Consensus Log Po/w :	-0.4

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.37
Solubility :	5.89 mg/ml ; 0.0427 mol/l
Class :	Very soluble
Log S (Ali) :	-1.31
Solubility :	6.7 mg/ml ; 0.0486 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.68
Solubility :	28.6 mg/ml ; 0.207 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.52

Safety of [ 71597-85-8 ]

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

Application In Synthesis of [ 71597-85-8 ]

* 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 [ 71597-85-8 ]
Downstream synthetic route of [ 71597-85-8 ]

[ 71597-85-8 ] Synthesis Path-Upstream 1~3

1
[ 80-07-9 ]
[ 71597-85-8 ]
[ 30809-75-7 ]

Reference： [1] Patent: US2011/288330, 2011, A1, . Location in patent: Page/Page column 15

2
[ 1511-62-2 ]
[ 71597-85-8 ]
[ 403648-76-0 ]

Reference： [1] Chinese Journal of Chemistry, 2018, vol. 36, # 2, p. 143 - 146

3
[ 71597-85-8 ]
[ 108-24-7 ]
[ 177490-82-3 ]

Reference： [1] Patent: US2006/4002, 2006, A1, . Location in patent: Page/Page column 41

[ 71597-85-8 ] Synthesis Path-Downstream 1~11

1
[ 352-34-1 ]
[ 71597-85-8 ]
[ 324-94-7 ]

Reference： [1]Chinese Journal of Chemistry,2015,vol. 33,p. 705 - 710
[2]Journal of labelled compounds and radiopharmaceuticals,2006,vol. 49,p. 817 - 827

2
[ 71597-85-8 ]
[ 263351-43-5 ]
[ 808769-21-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In DMF (N,N-dimethyl-formamide); water; at 80℃; for 16h;	A solution of the product of preparation 49 (0.75 g, 2.25 mmol), 4-hydroxy phenylboronic acid (0.62 g, 4.50 mmol) and 1, 1'- bis (diphenylphosphino) ferrocenyl palladium (II) chloride (0.11 g, 0.14 mrnol) in N, N-dimethylformamide (14 mL) was treated with 2M aqueous sodium carbonate solution (4 mL) and the resulting mixture was heated at 80 C for 16 hours. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel, eluting with ethyl acetate: pentane, 25: 75, to afford the title compound as a pale pink crystalline solid in quantitative yield, 0. 73 g. 'H NMR (400MHz, CDCI3) 8 : 1.47 (9H, s), 4. 33-4. 41 (2H, m), 4. 87-4. 94 (1H, bs), 6.89 (2H, d), 7.21 (1H, d), 7.37 (1H, dd), 7.43-7. 45 (4H, m); LRMS ESI m/z 298 [M-H]-
	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In DMF (N,N-dimethyl-formamide); water; at 80℃; for 16h;	A solution of the iodide from preparation 61 (0.75g, 2.25 mmol), 4-hydroxy phenylboronic acid (0.62g, 4.50 mmol), 1,1'-bis(diphenylphosphino)ferrocenyl palladium(II)chloride (0.11g, 0.14 mmol), in N,N-dimethylformamide (14 ml) was treated with 2M aqueous sodium carbonate (4 ml) and the resulting mixture heated at 80 C. under a nitrogen atmosphere for 16 hours. The solvent was removed in vacuo and the residue purified by column chromatography on silica gel eluting with ethyl acetate:pentane (1:3) to give the title compound as a pale pink crystalline solid (0.73g). 1HNMR (400 MHz, CDCl3) delta: 1.47 (s, 9H), 4.33-4.41 (m, 2H), 4.87-4.94 (bs, 1H), 6.89 (d, 2H), 7.21 (d, 1H), 7.37 (dd, 1H), 7.43-7.45 (m, 4H) ppm. MS (electrospray) m/z 298 [M-H]-, 322 [M+Na]+
	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In DMF (N,N-dimethyl-formamide); water; at 80℃; for 16h;	A solution of the iodide from preparation 131 (0.75 g, 2.25 mmol), 4-hydroxy phenylboronic acid (0.62 g, 4.50 mmol), 1,1'-Bis(diphenylphosphino)ferrocenyl palladium(II)chloride (0.11 g, 0.14 mmol), in N,N-dimethylformamide (14 ml) was treated with 2M aq. sodium carbonate (4 ml) and the resulting mixture heated at 80 C. under a nitrogen atmosphere for 16 hours. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with ethyl acetate:pentane (1:3) to give the title compound as a pale pink crystalline solid (0.73 g). 1HNMR (400 MHz, CDCl3) delta: 1.47 (s, 9H), 4.33-4.41 (m), 4.87-4.94 (bs, 1H), 6.89 (d, 2H), 7.21 (d, 1H), 7.37 (dd, 1H), 7.43-7.45 (m, 4H) ppm. MS (electrospray) m/z 298 [M-H]-, 322 [M+Na]+

With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In DMF (N,N-dimethyl-formamide); water; at 80℃; for 16h;

A solution of the iodide from preparation 75 (0.75g, 2.25mmol), 4-hydroxy phenylboronic acid (0.62g, 4.50mmol), 1,1'-bis(diphenylphosphino)ferrocenyl palladium(ll)chloride (0.11g, 0.14mmol), in A/,A/-dimethylformamide (14ml) wastreated with 2M aq. sodium carbonate (4ml) and the resulting mixture heated at 80C under a nitrogen atmosphere for 16 hours. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with ethyl acetate:pentane (1:3) to give the title compound as a pale pink crystalline solid ( 0.73g).1HNMR (400MHz, CDCI3) 5 : 7.43-7.45 (m, 4H), 7.37 (dd, 1H), 7.21 (d, 1H), 6.89 (d, 2H), 4.87-4.94 (bs, 1H), 4.33-4.41 (m, 2H), 1.47 (s, 9H) ppm.MS (electrospray) m/z 298 [M-H]", 322 [M+Naf

Reference： [1]Patent: WO2005/92840,2005,A1 .Location in patent: Page/Page column 73
[2]Patent: US2005/182091,2005,A1 .Location in patent: Page/Page column 32
[3]Patent: US2005/222128,2005,A1 .Location in patent: Page/Page column 47
[4]Patent: WO2004/108676,2004,A1 .Location in patent: Page 160-161

3
[ 71597-85-8 ]
[ 171663-13-1 ]
[ 808769-21-3 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation 12 : tert-Butyl [(4'-hydroxybiphenyl-3-yl)methyl]carbamate; Nitrogen was bubbled through a stirred solution of the bromide from preparation 11 (5.12Kg; 17.9 mol), 4-hydroxyphenylboronic acid (2.71 Kg; 19.7 mol) and sodium carbonate (2.848Kg; 26.8 mol) in a mixture of 1 ,4 dioxane (25.6L) and demineralised water (25.6L) at 20 to 250C for 1 hour. Then 1,1'-/s(diphenylphosphino)ferrocenyl palladium(ll)chloride(14.6g; 0.0179 mol) was added to the mixture and the nitrogen bubbling was continued for a further 30 minutes. Subsequently, the reaction was heated at 65 to 7O0C under a nitrogen blanket for 2 hours. The reaction was cooled to 20 to 25C, ethyl acetate (41 L) was added and the resulting mixture was stirred vigorously for 10 minutes, the phases were then separated. The organic phase was washed with a solution of citric acid (1.9Kg) in demineralised water (18.9L) followed by a solution of sodium chloride (3.15Kg) in demineralised water (18.9L). The ethyl acetate solution was treated with activated carbon (Darco KB 100mesh, wet powder; 5.12Kg) and stirred for 12 hours. The EPO <DP n="35"/>resulting slurry was then filtered through Arbocel and the cake was washed with methanol (25.6L). The combined filtrate was distilled and replaced with toluene under reduced pressure at 40 to 500C to a final volume of approximately 15L. The solution was then cooled to 10C over 2 hours and the resulting suspension was stirred at 1O0C for 12 hours. The product was isolated by filtration and washed with cyclohexane (2 x 2.56L) to provide the title compound as a white solid (4.26 Kg).1H NMR (400MHz1 CDCI3) delta: 1.47 (s, 9H), 4.33-4.41 (m, 2H), 4.87-4.94 (bs, 1H), 6.89 (d, 2H), 7.21 (d, 1H), 7.37 (dd, 1H), 7.43-7.45 (m, 4H) ppm. MS (electrospray) m/z 298 [M-H]", 322 [M+Na]+

Reference： [1]Organic Process Research and Development,2011,vol. 15,p. 1247 - 1255
[2]Patent: WO2007/10356,2007,A2 .Location in patent: Page/Page column 32-33

4
[ 71597-85-8 ]
[ 132131-24-9 ]
[ 1207354-24-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 2h;Heating / reflux;	Example 1 : {6-[4-(2-MorphoIin-4-yl-ethoxy)-phenyl]-quinazoIin-4-yI}-(4- morphoIin-4-yI-phenyI)-amine Step 1: 4-Amino-4'-(2-morphoIin-4-yl-ethoxy)-biphenyl-3-carbonitriIeA mixture of intermediate 1 ( 0.5g) 4-hydroxyphenylboronic acid (565mg) and tetrakis (triphenylphosphine) palladium (0) (290mg) in DME / 2M aqueous sodium carbonate (2:1, 15ml) was heated at reflux for 2hr. The cooled mixture was diluted with ethyl EPO <DP n="18"/>acetate and washed with further aqueous base. The organic phase was dried (MgSO4) and reduced onto silica gel. Flash chromatography with CH2Cl2 to 5% methanol in CH2Cl2 as eluant gave the coupling product, slightly contaminated with triphenylphosphine oxide by NMR. This material (340mg) was heated with 2- chloroethyl morpholine hydrochloride (330mg) and potassium carbonate (670mg) in acetone (20ml) at reflux overnight. The cooled reaction was partitioned between CH2Cl2 and 2M hydrochloric acid (aq). The acid phase was separated, basified and extracted with CH2Cl2 (2x),. These organic washes were concentrated to give the title compound as a brown solid (342mg) LC-MS rt 2.15 M+ 3241H NMR delta 7.55 (2H, m) ,7.38 (2H, d, J 8.21Hz), 6.95 ( 2H, d, J 8.21Hz), 6.78 (IH, m), 4.24 ( 2H, br s) 4.14 (2H, t, J 6.3Hz), 3.72 (4H, m), 2.82 (2H, m), 2.59 (4H5 m)

Reference： [1]Patent: WO2007/42782,2007,A1 .Location in patent: Page/Page column 16-17

5
[ 7499-66-3 ]
[ 71597-85-8 ]
[ 1071467-54-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	With water; sodium carbonate;tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; In ethanol; toluene; at 100℃;	4-(6-aminonaphthalen-2-yl)phenol (16)Palladium tetrakis(triphenylphosphine) (34.7 mg, 0.03 mmol) was added to a solution of compound 15 (200 mg, 0.9 mmol) and 4-hydroxyphenylboronic acid (165.5 mg, 1.2 mmol) in a mixed solvent of toluene (15 ml) and ethanol (5 ml), followed by the addition of tetrabutyl ammonium bromide (19 mg, 0.06 mmol) and sodium carbonate (2M aq., 4.0 ml). The solution was degassed by bubbling nitrogen for 10 min and then heated at 100 0C overnight. After cooling down to room temperature, the mixture was partitioned between ethyl acetate and water. <n="55"/>Organic layer was separated, washed with brine, dried over sodium sulfate and concentrated to about 5 ml using vacuum. Precipitate was filtered out and washed with cold methanol to obtain product 16 (151 mg, Y: 71 percent) as a pale yellow solid, which was already pure enough and was used directly in next step without further purification. 16: 1H NMR (DMSO-d6): delta 9.45 (IH, br), 7.80 (IH, b), 7.62 (IH, d, J= 8.8 Hz), 7.53 (4H, m), 6.93 (IH, d, A, J1 = 8.8 Hz, J2 = 2.0 Hz), 6.82 (3H, m), 5.35 (2H, b). HRMS (EI) m/z calcd. for [Ci6Hi3NO]+ 235.0097, found 235.0091.

Reference： [1]Patent: WO2008/124812,2008,A1 .Location in patent: Page/Page column 53-54

6
[ 80-07-9 ]
[ 71597-85-8 ]
[ 30809-75-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90℃; for 10h;	(1) The following reagents and solvents were put into a reaction container. 4,4'-dichlorodiphenyl sulfone: 10 g 4-hydroxyphenylboric acid: 5.8 g sodium hydrogen carbonate: 10 g dioxane: 400 ml water: 200 ml tetrakistriphenylphosphine palladium: 0.8 g Subsequently, the reaction solution was heated to 90 C. and agitation was performed at this temperature (90 C.) for 10 hours. At this time, the degree of proceeding of the reaction was ascertained with TLC appropriately. Then, the reaction was terminated with an ammonium chloride aqueous solution, and an organic phase was extracted with ethyl acetate. The resulting organic phase was washed with water and saturated saline solution in that order and was dried with anhydrous magnesium sulfate. A crude product obtained by concentrating the organic phase under reduced pressure was refined through column chromatography. The thus obtained product was used as-is in the following step.

Reference： [1]Patent: US2011/288330,2011,A1 .Location in patent: Page/Page column 15

7
[ 71597-85-8 ]
[ 16657-07-1 ]
[ 1279015-90-5 ]

Yield	Reaction Conditions	Operation in experiment
		7-Bromo-1H-indene (250 mg, 1.28 mmol), 4-hydroxyphenylboronic acid (212 mg, 1.54 mmol), sodium carbonate (270 mg, 2.56 mmol), Pd(PPh3)4 (catalytic amount), 1,4-dioxane (10 mL), and water (3 mL) were added, and stirred at 90 C for 8 hours. The solvent was distilled away under reduced pressure. Ethyl acetate was used as an extraction solvent, and after washing with a 1 N hydrochloric acid aqueous solution and saturated brine, the resultant was dried over magnesium sulfate. The solvent was distilled away under reduced pressure. To half of the resulting residue, methanol (10 mL) and a catalytic amount of 10% palladium-carbon were added, and stirred in a hydrogen atmosphere at room temperature overnight. The insoluble material was filtered off, and the solvent was distilled away under reduced pressure. An operation similar to that in Step 2 of Example 9 was performed on the resulting residue to thus obtain the title compound. Yield: 3.1 mg (0.007 mmol) MS (ESI, m/z) 442 [M+H]+

Reference： [1]Patent: EP2774917,2014,A1 .Location in patent: Paragraph 0105

8
[ 52414-98-9 ]
[ 71597-85-8 ]
3'-methyl-4'-nitro-[1,1'-biphenyl]-4-ol [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 89,p. 442 - 466

9
[ 13195-50-1 ]
[ 71597-85-8 ]
4-(5-nitrothiophen-2-yl)phenol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 8830 - 8847

10
[ 71597-85-8 ]
[ 34259-99-9 ]
[ 68535-57-9 ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 3h;Inert atmosphere;	In a 100mL three-necked flask, were added 4-hydroxyphenyl boronic acid (10.0g, 61.4mmol), 4- bromothiazole (10.2g, 73.7mmol), potassium carbonate (25.4g, 184.2mmol), 1,4- dioxane (30mmol), water (10mL) and bis triphenylphosphine palladium dichloride (2.15g, 3.07mmol). Under nitrogen, the reaction system was heated to 90 , stirred for 3h. Concentrated under reduced pressure to remove the solvent by distillation, the residue was dissolved in ethyl acetate (100 mL), saturated brine was added, extracted liquid separation. The combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated to give the crude product as a pale yellow oil, purified by column chromatography to give the title product as a beige solid.

Reference： [1]Patent: CN106866737,2017,A .Location in patent: Paragraph 0093; 0095; 0096

11
[ 16870-28-3 ]
[ 71597-85-8 ]
2-hydroxy-4-(4-hydroxyphenyl)benzoic acid potassium salt [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 7144 - 7167

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Technical Information

? Acidity of Phenols ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Chan-Lam Coupling Reaction ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Friedel-Crafts Reaction ? Halogenation of Phenols ? Hydrogenolysis of Benzyl Ether ? Oxidation of Phenols ? Pechmann Coumarin Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Reactions of Benzene and Substituted Benzenes ? Reimer-Tiemann Reaction ? Vilsmeier-Haack Reaction

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Ghs Precautionary Statements

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. 71597-85-8 ] {[proInfo.proName]}

Quality Control of [ 71597-85-8 ]

Related Doc. of [ 71597-85-8 ]

Product Citations Expand+

Product Details of [ 71597-85-8 ]

Calculated chemistry of [ 71597-85-8 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 71597-85-8 ]

Application In Synthesis of [ 71597-85-8 ]

[ 71597-85-8 ] Synthesis Path-Upstream 1~3

[ 71597-85-8 ] Synthesis Path-Downstream 1~11

Technical Information

Pharmaceutical Intermediates of [ 71597-85-8 ]

Honokiol Related Intermediates

Related Functional Groups of [ 71597-85-8 ]

Organoboron

Aryls

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Pharmaceutical Intermediates of
[ 71597-85-8 ]

Related Functional Groups of
[ 71597-85-8 ]