Pinacolborane

CAS: 25015-63-8

Ref. 3D-FP27048

Product Information

• Name: Pinacolborane
• Synonyms: 4,4,5,5-Tetramethyl-1,3,2-dioxaborolanePinacolatoborane, 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-, 2,3-Butanediol, 2,3-dimethyl-, cyclic ester with boronic acid, 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane, HBpin, Pinacolatoborane, Pinacolboane, Pinacolboronane, �Pinacolborane? (4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane

Description

Pinacolborane is a macrocyclic compound that is used as an inhibitor in organic synthesis. Pinacolborane binds to the active site of the enzyme, caproic acid, which prevents it from reacting with other molecules. Pinacolborane has been shown to have optimal reactivity in reactions involving macrolides and aryl halides. This compound has been synthesized by the reduction of pinacol with lithium aluminum hydride (LiAlH4) at low temperatures. The reaction mechanism involves electron transfer from LiAlH4 to pinacolborane, followed by hydrogenation of the resulting pinacol borane adduct. It can also be synthesized by dehydrogenative coupling of pinacolic acid with benzaldehyde or acetophenone, using copper(I) chloride (CuCl) as a catalyst. Pinacolboranes are also excellent catalysts for asymmetric synthesis reactions because they are homogeneous and easily prepared.

• Brand: Biosynth

Chemical properties

• Molecular weight: 127.98 g/mol
• Formula: C₆H₁₃BO₂
• Purity: Min. 98 Area-%