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Pinacolborane


Other Names:

4,4,5,5-Tetramethyl-1,3,2-dioxaborolane







General Information:


Structure:



CAS Number: 25015-63-8

Molecular Weight: 127.98 g/mol

Density: 42-43 C


Pinacolborane is a reagent typically used to form boronic esters. The boronic esters are usually formed by either Pd-catalyzed borylation or hydroboration. Bis(pinacolato)diboron is much more commonly used than pinacolborane for the Pd-catalyzed formation of boronic esters. Pinacolborane, however, is a more atom-economical boron source than bis(pinacolato)diboron.




Common Uses:


Reagent for the formation of pinacol boronate esters via Pd-catalyzed borylation





Reagent for the formation of pinacol boronate esters via hydroboration





Safety:


Pinacolborane is air and moisture sensitive. Incompatible with strong oxidizing agents, strong acids, bases, water, and alcohols.




References:


1) www.sigmaaldrich.com: 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane (link)

2) www.alfa.com: Pinacolborane (link)

3) K. L. Billingsley, S. L. Buchwald, J. Org. Chem., 2008, 73, 5589-5591.