CAS 87199-17-5 4-Formylphenylboronic acid - Materials / Alfa Chemistry

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4-Formylphenylboronic acid

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Catalog Number

ACM87199175

CAS Number

87199-17-5

Product Name

4-Formylphenylboronic acid

Structure

Category

Salt

Synonyms

Boronic acid, B-(4-formylphenyl)-

IUPAC Name

(4-formylphenyl)boronic acid

Molecular Weight

149.94

Molecular Formula

C7H7BO3

Canonical SMILES

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

InChI

InChI=1S/C7H7BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5,10-11H

InChI Key

VXWBQOJISHAKKM-UHFFFAOYSA-N

Boiling Point

347.6±44.0 °C

Melting Point

237-242 °C (lit.)

Flash Point

164.013ºC

Purity

99.5%+

Density

1.24±0.1 g/ml

Appearance

off-white powder

Application

4-Formylphenylboronic acid, appearing as a white to light yellow crystal powder, plays a crucial role in various chemical reactions and applications. Primarily utilized as a substrate in Suzuki cross-coupling reactions, it facilitates palladium-catalyzed Suzuki-Miyaura cross-couplings in aqueous environments. This versatile compound also participates in copper-mediated, ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides, and ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids. It is effective in triethylamine-catalyzed three-component Hantzsch condensations and copper-catalyzed nitrations, and it aids in the oxidative mono-cleavage of dialkenes, catalyzed by Trametes hirsuta. Additionally, it contributes to palladacycle-catalyzed cross-couplings of arylboronic acids with carboxylic anhydrides or acyl chlorides, and palladium-catalyzed aerobic oxidative cross-couplings. Its utility extends to synthesizing sensitizers featuring dithiafulvenyl units for high-efficiency dye-sensitized solar cells, developing novel protein synthesis inhibitors effective against Gram-positive bacteria, and conducting Suzuki aryl-aryl couplings on hexahomotrioxacalix[3]arene. Furthermore, it enables rhodium-catalyzed cyclizations that transform 1,5-enynes into cyclopentenes and spiro-cyclopentenes.

EC Number

617-982-7

Exact Mass

150.04900

Hazard Statements

C:Corrosive

Safety Description

S22-S26-S37/39-S45

WGK Germany

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