CAS 87199-17-5 4-Formylphenylboronic Acid (contains varying amounts of Anhydride)

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4-Formylphenylboronic Acid (contains varying amounts of Anhydride)

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Catalog Number

ACM87199175-1

CAS Number

87199-17-5

Product Name

4-Formylphenylboronic Acid (contains varying amounts of Anhydride)

Structure

Category

Liquid Crystal (LC) Building Blocks

Description

Liquid

IUPAC Name

(4-formylphenyl)boronic acid

Molecular Weight

149.94g/mol

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

Application

4-Formylphenylboronic Acid, available as a white to light yellow crystalline powder and containing varying amounts of anhydride, is primarily used as an essential substrate in Suzuki cross-coupling reactions. Its versatility extends to facilitating various chemical processes, including the palladium-catalyzed Suzuki-Miyaura cross-coupling in aqueous media and copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides. It serves as a reagent in ligand-free copper-catalyzed coupling reactions involving nitro arenes and arylboronic acids, as well as in triethylamine-catalyzed three-component Hantzsch condensations. Additionally, it is instrumental in copper-catalyzed nitrations, oxidative mono-cleavage of dialkenes catalyzed by Trametes hirsuta, and palladacycle-catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides. Furthermore, it supports palladium-catalyzed aerobic oxidative cross-coupling reactions, the synthesis of sensitizers with dithiafulvenyl units for high-efficiency dye-sensitized solar cells, and the development of novel protein synthesis inhibitors active against Gram-positive bacteria. Its utility also encompasses facilitating the Suzuki aryl-aryl coupling of the upper rim of hexahomotrioxacalix[3]arene and enabling rhodium-catalyzed cyclization to convert 1,5-enynes into cyclopentenes and spiro-cyclopentenes.

Complexity

130

Covalently-Bonded Unit Count

EC Number

438-670-5;617-982-7

Exact Mass

150.048824g/mol

Formal Charge

Heavy Atom Count

MeSH Entry Terms

4-formylphenylboronic acid;P-formylphenylboronic acid

Monoisotopic Mass