CAS 16419-60-6 o-Tolylboronic acid - Materials / Alfa Chemistry

NAVIGATION

o-Tolylboronic acid

PRICE INQUIRY

Catalog Number

ACM16419606-1

CAS Number

16419-60-6

Product Name

o-Tolylboronic acid

Structure

Category

Salt

IUPAC Name

(2-methylphenyl)boronic acid

Molecular Weight

135.96g/mol

Molecular Formula

C7H9BO2

Canonical SMILES

B(C1=CC=CC=C1C)(O)O

InChI

InChI=1S/C7H9BO2/c1-6-4-2-3-5-7(6)8(9)10/h2-5,9-10H,1H3

InChI Key

NSJVYHOPHZMZPN-UHFFFAOYSA-N

Melting Point

166.5 °C

Application

o-Tolylboronic acid is an important organic boronic acid compound utilized predominantly in the Suzuki-Miyaura cross-coupling reactions catalyzed by palladium, particularly in aqueous environments. It also serves as a reagent in Ruthenium-catalyzed direct arylation and ligand-free copper-catalyzed coupling reactions, as well as Rhodium-catalyzed asymmetric 1,4-addition reactions. Additionally, it plays a significant role in the preparation of chiral monophosphorus ligands for asymmetric Suzuki-Miyaura coupling reactions, contributing to the synthesis of human farnesyl pyrophosphate synthase inhibitors, which have demonstrated potential as antitumor agents targeting multiple myeloma cells. Overall, o-Tolylboronic acid holds substantial importance in organic synthesis and finds applications in the medical and chemical industries.

Complexity

106

Covalently-Bonded Unit Count

Exact Mass

136.06956g/mol

Formal Charge

Heavy Atom Count

MeSH Entry Terms

para-tolylboronic acid;tolylboronic acid

Monoisotopic Mass

136.06956g/mol

Rotatable Bond Count