CAS 72824-04-5 Allylboronic acid pinacol ester

NAVIGATION

Allylboronic acid pinacol ester

PRICE INQUIRY

Catalog Number

ACM72824045

CAS Number

72824-04-5

Product Name

Allylboronic acid pinacol ester

Structure

Category

Salt

Synonyms

4,4,5,5-Tetramethyl-2-(2-propen-1-yl)-1,3,2-dioxaborolane

IUPAC Name

4,4,5,5-tetramethyl-2-prop-2-enyl-1,3,2-dioxaborolane

Molecular Weight

168.04

Molecular Formula

C9H17BO2

Canonical SMILES

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

InChI

InChI=1S/C9H17BO2/c1-6-7-10-11-8(2,3)9(4,5)12-10/h6H,1,7H2,2-5H3

InChI Key

YMHIEPNFCBNQQU-UHFFFAOYSA-N

Boiling Point

50-53 °C 5mmHg (lit.)

Purity

99.5%+

Density

0.896 g/ml

Appearance

Clear colorless liquid

Application

Allylboronic acid pinacol ester, a clear, colorless liquid, serves as a versatile reagent used in various chemical reactions. It plays a crucial role in Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions and olefin metathesis, allowing for the formation of complex molecular structures. Additionally, this compound facilitates intermolecular radical additions and allylboration of aldehydes when catalyzed by chiral spirobiindane diol (SPINOL) based phosphoric acids. It is also instrumental in Cobalt-catalyzed regioselective hydrovinylation of dienes with alkenes. Furthermore, allylboronic acid pinacol ester is used in nucleic acid-templated energy transfer processes, which can lead to photorelease reactions, demonstrating its broad utility in advanced synthetic chemistry applications.

Complexity

171

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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