4-Mercaptophenylboronic acid supplier

Name
4-Mercaptophenylboronic acid
EINECS
CAS No. 237429-33-3
Article Data2
CAS DataBase
Density 1.27 g/cm³
Solubility
Melting Point >230 °C(lit.)
Formula C₆H₇BO₂S
Boiling Point 329.4 °C at 760 mmHg
Molecular Weight 153.997
Flash Point 153 °C
Transport Information
Appearance
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Boronicacid, (4-mercaptophenyl)- (9CI);(4-sulfanylphenyl)boronic acid;
PSA 79.26000
LogP -0.34490

Synthetic route

: 237429-34-4
4-[(dimethyl-tert-butyl-silyl)thio]-phenylboronic acid

: 237429-33-3
4-mercaptophenylboronic acid

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane desilylation;	88%

: 76-05-1
trifluoroacetic acid

: 237429-34-4
4-[(dimethyl-tert-butyl-silyl)thio]-phenylboronic acid

: 237429-33-3
4-mercaptophenylboronic acid

Conditions

Conditions	Yield
In dichloromethane equimolar amts., stirring overnight; evapn. (reduced pressure), crystn. (water);	88%

: 106-53-6
para-bromobenzenethiol

: 237429-33-3
4-mercaptophenylboronic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 92 percent / sodium hydride in oil / tetrahydrofuran / 14 h / 20 °C 2.1: n-butyl lithium / tetrahydrofuran; hexane / 0.25 h / -78 °C 2.2: 77 percent / tri-isopropyl borate / tetrahydrofuran / 4 h / -78 - -20 °C 3.1: 88 percent / trifluoroacetic acid / CH2Cl2 View Scheme

: 153312-70-0
(4-bromophenylsulfanyl)-tert-butyldimethylsilane

: 237429-33-3
4-mercaptophenylboronic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyl lithium / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 77 percent / tri-isopropyl borate / tetrahydrofuran / 4 h / -78 - -20 °C 2.1: 88 percent / trifluoroacetic acid / CH2Cl2 View Scheme

: C10H13BOS

: 237429-33-3
4-mercaptophenylboronic acid

Conditions

Conditions	Yield
With sodium hydroxide In water pH=11 - 12; Large scale;	1.93 kg

: 76-09-5
2,3-dimethyl-2,3-butane diol

: 237429-33-3
4-mercaptophenylboronic acid

: 1029438-23-0
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenethiol

Conditions

Conditions	Yield
With sodium sulfate at 20℃; for 16h; Inert atmosphere;	100%
With magnesium sulfate In diethyl ether at 20℃;	98%
With magnesium sulfate In cyclohexane at 20℃;	98%

: 105-36-2
ethyl bromoacetate

: 237429-33-3
4-mercaptophenylboronic acid

: 1211474-17-7
{4-[(2-ethoxy-2-oxoethyl)thio]phenyl}boronic acid

Conditions

Conditions	Yield
With potassium carbonate; sodium iodide In acetonitrile at 20℃; for 18h;	100%

: 76-84-6
triphenylmethyl alcohol

: 237429-33-3
4-mercaptophenylboronic acid

: 1310810-82-2
4-(tritylsulfanyl)phenylboronic acid

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 1h;	95%

: N'-(cyclohexylmethyl)-N'-((1R,2S,E)-1-hydroxy-1,4-diphenylbut-3-en-2-yl)-4-methoxybenzohydrazide

: 237429-33-3
4-mercaptophenylboronic acid

: 4-((7S,8R,Z)-6-(cyclohexylmethyl)-4-(4-methoxyphenyl)-8-phenyl-7-((E)-styryl)-7,8-dihydro-6H-1,3,5,6,2-dioxadiazaborocin-2-yl)benzenethiol

Conditions

Conditions	Yield
In dichloromethane at 40℃; for 0.5h;	95%

: 96-27-5
rac-3-sulfanylpropane-1,2-diol

: 237429-33-3
4-mercaptophenylboronic acid

: C9H11BO2S2

Conditions

Conditions	Yield
In toluene at 20℃; for 24h; Molecular sieve; Glovebox;	94.8%

: 1260364-42-8
C14H15BrN2O3S3

: 237429-33-3
4-mercaptophenylboronic acid

: 1260364-52-0
C20H20N2O3S4

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; acetonitrile at 100℃; Suzuki coupling; Microwave irradiation;	88%

: 5355-61-3, 5381-86-2, 59825-14-8, 77291-92-0, 108391-15-7, 5471-97-6
1,3-diphenyl-1,3-propanediol

: 237429-33-3
4-mercaptophenylboronic acid

: d,l-(4,6-diphenyl-2-(4-mercaptophenyl))-1,3,2-dioxaborinane

Conditions

Conditions	Yield
In tetrahydrofuran for 0.5h; Esterification;	86%
In tetrahydrofuran equimolar amts., stirring for 30 min; drying (Na2SO4), filtration, evapn., chromy. (SiO2, CH2Cl2);	86%

: 105-59-9
N-Methyldiethanolamine

: 237429-33-3
4-mercaptophenylboronic acid

: 2-(4-mercaptophenyl)-6-methyl-1,3,6,2-dioxaazaborocane

Conditions

Conditions	Yield
In tetrahydrofuran for 0.5h; Esterification;	85%

: 105-59-9
N-Methyldiethanolamine

: 237429-33-3
4-mercaptophenylboronic acid

: 237429-36-6
2-(4-mercaptophenyl)-6-methyl-1,3,6,2-dioxaazaborocane

Conditions

Conditions	Yield
In tetrahydrofuran 1.1 equiv. of amine, stirring for 30 min; Et2O addn., washing (water), drying (Na2SO4), evapn.;	85%

: 36865-41-5
3-bromopropanol methyl ether

: 237429-33-3
4-mercaptophenylboronic acid

: 1032825-16-3
(4-{[3-(methoxy)propyl]thio}phenyl)boronic acid

Conditions

Conditions	Yield
With potassium carbonate; sodium iodide In acetonitrile at 20℃;	81%

: 5292-43-3
bromoacetic acid tert-butyl ester

: 237429-33-3
4-mercaptophenylboronic acid

: 237429-41-3
4-(((butyloxycarbonyl)methyl)thio)phenylboronic acid

Conditions

Conditions	Yield
With potassium carbonate; sodium iodide In acetonitrile for 20h; Alkylation;	71%
With potassium carbonate; sodium iodide In acetonitrile 1.5 equiv. of K2CO3 and t-BuO2CCH2Br, 0.15 equiv. NaI, stirring for 20 h; evapn. (reduced pressure), water addn., extn. into CH2Cl2, washing (water), drying (Na2SO4), chromy. (SiO2, 2% MeOH in CH2Cl2);	71%

: [Pt(2,2':6',2''-terpyridine)(acetonitrile)](nitrate)2

: 237429-33-3
4-mercaptophenylboronic acid

: (2,2':6',2''-terpyridine)(4-mercaptophenylboronic acid(1-))platinum(II) nitrate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide addn. of DMF soln. of pyridine deriv. to DMF soln. of palladium compd., stirring at room temp. for 1 h; ppn. with diethyl ether, centrifugation, washing with diethyl ether, elem. anal.;	63%

: 61817-93-4, 146143-79-5, 871132-66-0
bis(acetonitrile)decacarbonyltriosmium

: 237429-33-3
4-mercaptophenylboronic acid

: C16H7BO12Os3S

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃;	63%

: 237429-33-3
4-mercaptophenylboronic acid

: 74-88-4
methyl iodide

: 98546-51-1
(4-thiomethoxyphenyl)boronic acid

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile Methylation;	61%
With potassium carbonate In acetonitrile excess of MeI, stirring overnight; water addn., extn. into CH2Cl2, washing (water), drying (Na2SO4), evapn. (reduced pressure), recrystn. (Et2O);	61%

: 1078734-14-1
2-bromo-5-(3-methoxyphenyl)thiophene

: 237429-33-3
4-mercaptophenylboronic acid

: 1193525-23-3
4-[5-(3-methoxyphenyl)-2-thienyl]benzenethiol

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; ethanol; water at 150℃; under 11251.1 Torr; for 0.25h; Suzuki coupling; Microwave irradiation;	61%

: 1-(2-chloroethyl)-N,N-dimethylpiperidin-4-amine

: 237429-33-3
4-mercaptophenylboronic acid

: [4-({2-[4-(dimethylamino)piperidin-1-yl]ethyl}thio)phenyl]boronic acid

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran at 130℃; for 6h; Microwave irradiation;	53%

: 683-57-8
bromo-acetic acid amide

: 237429-33-3
4-mercaptophenylboronic acid

: 1032825-15-2
{4-[(2-amino-2-oxoethyl)thio]phenyl}boronic acid

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃;	49%

: 850221-69-1
2-chloro-6-(1-oxo-[4-methoxyphenyl]methyl)pyrazine

: 237429-33-3
4-mercaptophenylboronic acid

: 1149759-63-6
6-(4-mercaptophenyl)-2-((4-methoxyphenyl)carbonyl)pyrazine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 5h; Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;	43%

: 954114-30-8
3-cyanopropyl(dimethyl)(vinyl)silane

: 237429-33-3
4-mercaptophenylboronic acid

: [4-({2-[(3-cyanopropyl)dimethylsilyl]ethyl}thio)phenyl]boronic acid

Conditions

Conditions	Yield
With di-tert-butyl peroxide at 100℃; for 6h; Inert atmosphere; Sealed tube;	43%

: 7764-29-6
N,N'-thiobisphthalimide

: 237429-33-3
4-mercaptophenylboronic acid

: C14H10BNO4S2

Conditions

Conditions	Yield
In 1,2-dichloro-ethane at 80℃;	42%

: 700835-81-0
4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-(propan-2-yl)-1,2-oxazole

: 237429-33-3
4-mercaptophenylboronic acid

: 1020577-19-8
[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}thio)phenyl]boronic acid

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 24h;

: 237429-33-3
4-mercaptophenylboronic acid

: 4-((carboxymethyl)thio)phenylboronic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent / tetrahydrofuran / 0.5 h 2: 65 percent / potassium carbonate; sodium iodide / acetonitrile / 20 h 3: 80 percent / trifluoroacetic acid / CH2Cl2 View Scheme
Multi-step reaction with 2 steps 1: 71 percent / potassium carbonate; sodium iodide / acetonitrile / 20 h 2: 80 percent / trifluoroacetic acid / CH2Cl2 View Scheme

: 237429-33-3
4-mercaptophenylboronic acid

: 2-(4-(t-butyloxycarbonylmethylthiophenyl))-6-methyl-1,3,6,2-dioxaazaborocane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / tetrahydrofuran / 0.5 h 2: 65 percent / potassium carbonate; sodium iodide / acetonitrile / 20 h View Scheme

: 237429-33-3
4-mercaptophenylboronic acid

: 2-(4-carboxymethylthiophenyl)-4,6-diphenyl-1,3,2-dioxaborinane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / tetrahydrofuran / 0.5 h 2: 70 percent / potassium carbonate; sodium iodide / acetonitrile / 20 h 3: 54 percent / trifluoroacetic acid / CH2Cl2 / 2 h View Scheme

: 237429-33-3
4-mercaptophenylboronic acid

: d,l-2-(4-(t-butyloxycarbonylmethylthiophenyl))-4,6-diphenyl-1,3,2-dioxaborinane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / tetrahydrofuran / 0.5 h 2: 70 percent / potassium carbonate; sodium iodide / acetonitrile / 20 h View Scheme

: 728-87-0
4,4'-Dimethoxybenzhydrol

: 237429-33-3
4-mercaptophenylboronic acid

: 945244-19-9
4-(4,4'-dimethoxybenzhydryl)thiophenylboronic acid

Conditions

Conditions	Yield
With acetic acid at 60℃; for 1h;
In acetic acid at 60℃; for 1h;
In acetic acid
With acetic acid at 60℃; for 1h;

4-Mercaptophenylboronic acid Specification

The Boronic acid,B-(4-mercaptophenyl)-, with the CAS registry number 237429-33-3, has the systematic name of (4-sulfanylphenyl)boronic acid. It belongs to the following product categories: Benzene Series; Boronic Acid; Aryl; Boronic Acids; Boronic Acids and Derivatives; Boronic Acids. And the molecular formula of the chemical is C₆H₇BO₂S.

The characteristics of Boronic acid,B-(4-mercaptophenyl)- are as followings: (1)ACD/LogP: 1.89; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.75; (4)ACD/LogD (pH 7.4): 0.39; (5)ACD/BCF (pH 5.5): 11.58; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 182.9; (8)ACD/KOC (pH 7.4): 7.95; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 43.76 Å²; (13)Index of Refraction: 1.594; (14)Molar Refractivity: 41.13 cm³; (15)Molar Volume: 121.1 cm³; (16)Polarizability: 16.3×10^-24cm³; (17)Surface Tension: 50.5 dyne/cm; (18)Density: 1.27 g/cm³; (19)Flash Point: 153 °C; (20)Enthalpy of Vaporization: 60.36 kJ/mol; (21)Boiling Point: 329.4 °C at 760 mmHg; (22)Vapour Pressure: 7.17E-05 mmHg at 25°C.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: OB(O)c1ccc(S)cc1
(2)InChI: InChI=1/C6H7BO2S/c8-7(9)5-1-3-6(10)4-2-5/h1-4,8-10H
(3)InChIKey: AUVSUPMVIZXUOG-UHFFFAOYAO

Product Name

4-Mercaptophenylboronic acid

Synthetic route

4-Mercaptophenylboronic acid Specification

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