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2-Bromophenylboronic acid

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Name

2-Bromophenylboronic acid

EINECS -0
CAS No. 244205-40-1 Density 1.671 g/cm3
PSA 40.46000 LogP 0.12890
Solubility Soluble in methanol. Slightly soluble in water. Melting Point 109-114 °C
Formula C6H6BBrO2 Boiling Point 329.17 °C at 760 mmHg
Molecular Weight 200.827 Flash Point 152.877 °C
Transport Information N/A Appearance White to off-white powder
Safety 37/39-26 Risk Codes 36/37/38-22
Molecular Structure Molecular Structure of 244205-40-1 (2-Bromophenylboronic acid) Hazard Symbols IrritantXi,HarmfulXn
Synonyms

Boronicacid, (2-bromophenyl)- (9CI);

 

2-Bromophenylboronic acid Synthetic route

potassium (2-bromophenyl)trifluoroborate

244205-40-1

(2-bromophenyl)boronic acid

Conditions
ConditionsYield
With iron(III) chloride; water In tetrahydrofuran at 20℃; for 0.5h;91%
121-43-7

Trimethyl borate

583-53-9

1,2-dibromobenzene

244205-40-1

(2-bromophenyl)boronic acid

Conditions
ConditionsYield
With LiC(CH3)3; HCl In tetrahydrofuran; diethyl ether (under Ar, Schlenk); soln. of o-dibromobenzene, THF-Et2O cooled to -115°C, LiC(CH3)3 (-78°C) added, stirred for 35 min at -115°C, treated with B(OCH3)3 in Et2O (-78°C), stirred for 2 h at -115-105°C; quenched with EtOH/HCl at -115°C, warmed to room temp., extd. with Et2O, organic layer washed with brine, H2O, dried over MgSO4, solvent removed by rotary evaporator, residue refluxed in H2O for 2 h, filtered,recrystd. from H2O; elem. anal.;66%

diisopropyl (2-bromophenyl)boronate

244205-40-1

(2-bromophenyl)boronic acid

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; hexane; toluene at 20℃; for 0.5h;
583-53-9

1,2-dibromobenzene

244205-40-1

(2-bromophenyl)boronic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triisopropyl borate; n-butyllithium / toluene; tetrahydrofuran; hexane / 2.08 h / -70 - 20 °C
2: aq. HCl / toluene; tetrahydrofuran; hexane / 0.5 h / 20 °C
View Scheme

C8H10BBrO2

244205-40-1

(2-bromophenyl)boronic acid

Conditions
ConditionsYield
With hydrogenchloride; water In tetrahydrofuran; diethyl ether; ethanol; pentane at -115 - 20℃;0.55 g
583-55-1

1-Bromo-2-iodobenzene

244205-40-1

(2-bromophenyl)boronic acid

Conditions
ConditionsYield
Stage #1: 1-Bromo-2-iodobenzene With isopropylmagnesium chloride In tetrahydrofuran at -42℃; for 2h; Inert atmosphere;
Stage #2: With Triisopropyl borate In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #3: With sodium hydroxide In tetrahydrofuran; water for 1h; Inert atmosphere;
121-43-7

Trimethyl borate

583-55-1

1-Bromo-2-iodobenzene

244205-40-1

(2-bromophenyl)boronic acid

Conditions
ConditionsYield
Stage #1: 1-Bromo-2-iodobenzene With lithium acetate; 1-propylmagnesium chloride; 3-butyl-1-methylimidazolium acetate In tetrahydrofuran at 0 - 10℃; for 4h; Inert atmosphere;
Stage #2: Trimethyl borate In tetrahydrofuran at 10℃; for 3h; Inert atmosphere;
Stage #3: With acetic acid at 15℃; for 0.333333h; Inert atmosphere;
86.83 g
126-30-7

2,2-Dimethyl-1,3-propanediol

244205-40-1

(2-bromophenyl)boronic acid

884010-16-6

2,2-dimethylpropane-1,3-diyl [2-bromophenyl] boronate

Conditions
ConditionsYield
In toluene for 1h; Heating;100%
In dichloromethane at 20℃; for 3.5h;100%
In benzene Reflux;
In diethyl ether at 20℃; Inert atmosphere; Molecular sieve;
2943-42-2

di(4-methyl)phenylthiosulfonate

244205-40-1

(2-bromophenyl)boronic acid

15861-49-1

1-bromo-2-(4-methylphenylsulfanyl)benzene

Conditions
ConditionsYield
With sodium hydrogencarbonate; copper(II) sulfate In methanol at 20℃; for 24h; Inert atmosphere;100%
With sodium hydrogencarbonate; copper(II) sulfate In methanol at 20℃; for 24h; Inert atmosphere;95%
244205-40-1

(2-bromophenyl)boronic acid

1-bromo-4-fluoro-2-iodobenzene

2,2′-dibromo-5-fluoro-1,1′-biphenyl

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 110℃; Inert atmosphere;100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 90℃; Inert atmosphere;93%

2-Bromophenylboronic acid Specification

The 2-Bromophenylboronic acid, with the CAS registry number 244205-40-1, is also known as Boronic acid, B-(2-bromophenyl)-. It belongs to the product categories of Blocks; Boronic Acids; Bromides; B (Classes of Boron Compounds); Aryl; Boronic Acids and Derivatives. This chemical's molecular formula is C6H6BBrO2 and molecular weight is 200.83. What's more, its systematic name is (2-Bromophenyl)boronic acid. This chemical should be sealed and stored in a cool, ventilated and dry place. Moreover, it should be protected from oxides.

Physical properties of 2-Bromophenylboronic acid are: (1)ACD/LogP: 2.361; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.36; (4)ACD/LogD (pH 7.4): 2.30; (5)ACD/BCF (pH 5.5): 36.61; (6)ACD/BCF (pH 7.4): 32.17; (7)ACD/KOC (pH 5.5): 457.73; (8)ACD/KOC (pH 7.4): 402.23; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 40.46 Å2; (13)Index of Refraction: 1.598; (14)Molar Refractivity: 41.01 cm3; (15)Molar Volume: 120.196 cm3; (16)Polarizability: 16.257×10-24cm3; (17)Surface Tension: 52.0 dyne/cm; (18)Density: 1.671 g/cm3; (19)Flash Point: 152.877 °C; (20)Enthalpy of Vaporization: 60.34 kJ/mol; (21)Boiling Point: 329.17 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: Brc1ccccc1B(O)O
(2)Std. InChI: InChI=1S/C6H6BBrO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4,9-10H
(3)Std. InChIKey: PLVCYMZAEQRYHJ-UHFFFAOYSA-N  

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