Allylboronic acid pinacol ester

CAS: 72824-04-5

Ref. 3D-FA38545

Product Information

• Name: Allylboronic acid pinacol ester
• Synonyms: 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 4,4,5,5-Tetramethyl-2-Prop-2-En-1-Yl-1,3,2-Dioxaborolane
• CAS: 72824-04-5

Description

Allylboronic acid pinacol ester is an allylation reagent that is used to produce aldehydes from ketones. It reacts with water, yielding the desired product and formaldehyde as a byproduct. The reaction proceeds through a sequence of steps, in which the boronate ester first reacts with water to form an allylboronate ion and hydrogen gas. This intermediate then reacts with potassium t-butoxide to produce the desired allyl alcohol and potassium borohydride. Finally, the palladium complex catalyst reduces the carbonyl group of the starting material, converting it into an aldehyde. Allylboronic acid pinacol ester is commercially available as a white solid, but can also be synthesized from 2-chloro-5-pinacolylborane (pinacol) in high yield using catalytic cross coupling reactions.

• Brand: Biosynth

Chemical properties

• Molecular weight: 168.04 g/mol
• Formula: C₉H₁₇BO₂
• Purity: Min. 95%
• InChI: InChI=1S/C9H17BO2/c1-6-7-10-11-8(2,3)9(4,5)12-10/h6H,1,7H2,2-5H3
• InChI key: InChIKey=YMHIEPNFCBNQQU-UHFFFAOYSA-N
• SMILES: C=CCB1OC(C)(C)C(C)(C)O1