4-Bromophenylboronic acid Chemical Properties

Melting point:

284-288 °C (lit.)

Boiling point:

315.0±44.0 °C(Predicted)

Density 

1.67±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Crystalline Powder

pka

8.32±0.10(Predicted)

color 

Off-white to light beige

Water Solubility 

Soluble in methanol. Insoluble in water.

BRN 

2936347

InChI

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

InChIKey

QBLFZIBJXUQVRF-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

5467-74-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-22

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

CY8650000

TSCA 

T

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

• Language:English Provider:4-Bromobenzeneboronic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Bromophenylboronic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

suzuki reaction

Uses

4-Bromobenzeneboronic acid is a reagent used for Palladium catalyzed Suzuki-Miyaura cross-couplings, Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence. It is also used in the preparation of Protein modulators and enzymatic and kinase inhibitors, Gallate-based obovatol analogs with potential anti-tumor activity. It is used as a reagent for Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides, Pd-catalyzed arylative cyclization of alkyne-tethered enals or enones via carbopalladation of alkynes, Copper-catalyzed cross-couplings.

Uses

Labelled 4-Bromophenylboronic Acid (B686545). 4-Bromophenylboric acid is used in the preparation of arylboronates as inhibitors of fatty acid amide hydrolase.

Synthesis

GENERAL METHOD: 4-Bromoaniline (0.5 mmol, 1.0 eq.) was dissolved in methanol (1.0 mL), hydrochloric acid (0.5 mL, 1.5 mmol, 3.0 eq.) and water (0.5 mL) were added. The reaction mixture was stirred for 2 min and then sodium nitrite solution (0.25 mL, prepared by dissolving 35 mg of sodium nitrite in 0.25 mL of water) was added. Stir at 0-5 °C for 30 min, followed by the addition of hydrochloric acid (135 mg, 1.5 mmol, 3.0 equiv) in methanol (1.0 mL). Stirring was continued for 60 min. After completion of the reaction, it was diluted with water (10 mL) and extracted with dichloromethane (50 mL, 3 times). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 4-bromophenylboronic acid.

References

[1] Synlett, 2014, vol. 25, # 11, p. 1577 - 1584
[2] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612

4-Bromophenylboronic acid(5467-74-3)Related Product Information

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• Triphenylphosphine
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