CAS 126726-62-3 Isopropenylboronic acid pinacol ester

NAVIGATION

Isopropenylboronic acid pinacol ester

PRICE INQUIRY

Catalog Number

ACM126726623

CAS Number

126726-62-3

Product Name

Isopropenylboronic acid pinacol ester

Structure

Category

Salt

IUPAC Name

4,4,5,5-tetramethyl-2-prop-1-en-2-yl-1,3,2-dioxaborolane

Molecular Weight

168.04g/mol

Molecular Formula

C9H17BO2

Canonical SMILES

B1(OC(C(O1)(C)C)(C)C)C(=C)C

InChI

InChI=1S/C9H17BO2/c1-7(2)10-11-8(3,4)9(5,6)12-10/h1H2,2-6H3

InChI Key

SVSUYEJKNSMKKW-UHFFFAOYSA-N

Purity

96%

Application

Isopropenylboronic acid pinacol ester serves as a highly versatile reagent in a variety of chemical reactions, including the palladium-catalyzed Suzuki-Miyaura cross-coupling, inverse-electron-demand Diels-Alder reaction, Simmons-Smith cyclopropanation, polyene cyclization, and stereoselective aldol reactions. It is also integral to Grubbs cross-metathesis, intramolecular Suzuki-Miyaura reactions, stereoselective cross-metathesis, dipolar cycloaddition, iodosulfonylation, asymmetric conjugate addition, and intramolecular hydroacylation. Notably, this ester plays a crucial role in the synthesis of therapeutic kinase and enzymatic inhibitors. Its applications extend to serving as an intermediate in the preparation of both cyclic and acyclic organic compounds, and it has been demonstrated that its α-Substituted Allyl/Crotyl variant can achieve highly diastereo- and enantioselective allylboration of aldehydes.

Complexity

193

Covalently-Bonded Unit Count

Exact Mass

168.13216g/mol

Formal Charge

Heavy Atom Count

Monoisotopic Mass

168.13216g/mol

Rotatable Bond Count

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