ChemicalBook Product Catalog Chemical Reagents Organic reagents Boric acid 4-Bromophenylboronic acid

4-Bromophenylboronic acid

Product Name4-Bromophenylboronic acid
CAS5467-74-3
MFC6H6BBrO2
MW200.83
EINECS226-779-9
MOL File5467-74-3.mol

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
pka	8.32±0.10(Predicted)
form	Crystalline Powder
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
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

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

Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

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

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

suzuki reaction

Synthesis

106-40-1

5467-74-3

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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