CAS 244205-40-1 2-Bromophenylboronic acid - Materials / Alfa Chemistry

NAVIGATION

2-Bromophenylboronic acid

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Catalog Number

ACM244205401-1

CAS Number

244205-40-1

Product Name

2-Bromophenylboronic acid

Structure

Category

Salt; Other Electronic Materials

Synonyms

Boronic acid,B-(2-bromophenyl)-

IUPAC Name

(2-bromophenyl)boronic acid

Molecular Weight

200.83

Molecular Formula

C6H6BBrO2

Canonical SMILES

B(C1=CC=CC=C1Br)(O)O

InChI

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

InChI Key

PLVCYMZAEQRYHJ-UHFFFAOYSA-N

Boiling Point

329.2±44.0 °C

Melting Point

113 °C (lit.)

Purity

99.5%+

Density

1.67±0.1 g/ml

Application

2-Bromophenylboronic acid, appearing as a white to off-white powder, is a versatile boronic acid derivative prominently utilized in organic synthesis. Its primary function is to facilitate carbon-carbon bond formation, most notably in Suzuki coupling reactions, where aryl halides are paired with boronic acids or their esters in the presence of Pd(PPh3)4 to achieve this bond formation efficiently. Additionally, it serves as an inhibitor of hormone-sensitive lipase and plays a vital role in catalyzing amide bond formation between amines and carboxylic acids, promoting greener amidation processes by eliminating the need for preactivation or coupling reagents. Beyond these applications, 2-Bromophenylboronic acid is a crucial intermediate in the production of Organic Light-Emitting Diodes (OLEDs), underscoring its significance in both chemical synthesis and advanced material development.

Complexity

110

Covalently-Bonded Unit Count

Exact Mass

199.96442g/mol

Formal Charge

Heavy Atom Count

Monoisotopic Mass

199.96442g/mol

Rotatable Bond Count

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