3-Bromophenylboronic acid Chemical Properties

Melting point:

164-168 °C (lit.)

Boiling point:

330.5±44.0 °C(Predicted)

Density 

1.67±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

7.55±0.10(Predicted)

form 

Crystalline Powder

color 

White

BRN 

3127104

InChI

InChI=1S/C6H6BBrO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4,9-10H

InChIKey

AFSSVCNPDKKSRR-UHFFFAOYSA-N

SMILES

B(C1=CC=CC(Br)=C1)(O)O

CAS DataBase Reference

89598-96-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Bromophenylboronic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

Reactant involved in a variety of organic reactions including:• ;Oxidative cross coupling1,2• ;Gold salt catalyzed homocoupling3• ;1,4-Addition reactions with α,β-unsaturated ketones4• ;Enantioselective addition reactions5• ;Suzuki-Miyaura coupling for synthesis of anthranilamide-protected arylboronic acids6• ;C-H Functionalization of quinones7

Uses

suzuki reaction

Uses

Reactant involved in a variety of organic reactions including:

• Oxidative cross coupling
• Gold salt catalyzed homocoupling
• 1,4-Addition reactions with α,β-unsaturated ketones
• Enantioselective addition reactions
• Suzuki-Miyaura coupling for synthesis of anthranilamide-protected arylboronic acids
• C-H Functionalization of quinones

Synthesis

In a 500 mL round bottom flask, 1-bromo-3-iodobenzene (25.0 g, 88 mmol) was dissolved in 200 mL of tetrahydrofuran. The reaction solution was cooled to -78°C under nitrogen protection. n-Butyllithium (60.75 mL, 97 mmol) was slowly added dropwise to the cooled solution over a period of 30 minutes and stirring was continued at the same temperature for 1 hour. Subsequently, trimethyl borate (11 g, 106 mmol) was added dropwise at the same temperature, and then the mixture was gradually warmed to room temperature and stirred overnight. Upon completion of the reaction, 2 equivalents of hydrochloric acid was added dropwise to the reaction solution for acidification and stirring was continued for 1 hour. The reaction mixture was extracted with ethyl acetate, the organic layers were combined and concentrated under reduced pressure. The resulting crystals were dissolved in cold hexane to give Intermediate 11-a (12 g, 67.6% yield).

References

[1] Patent: KR2015/130206, 2015, A. Location in patent: Paragraph 0862-0867
[2] Patent: KR2016/13678, 2016, A. Location in patent: Paragraph 0324-0330

3-Bromophenylboronic acid(89598-96-9)Related Product Information

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