473294

Bis(pinacolato)diboron

99%

• Synonym(s): 4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi-1,3,2-dioxaborolane
• Empirical Formula (Hill Notation): C₁₂H₂₄B₂O₄
• CAS Number: 73183-34-3
• Molecular Weight: 253.94
• MDL number: MFCD00799570
• UNSPSC Code: 12352103
• PubChem Substance ID: 24870893
• NACRES: NA.22

Properties

• Assay: 99%
• form: powder (or crystals)
• mp: 137-140 °C (lit.)
• SMILES string: CC1(C)OB(OC1(C)C)B2OC(C)(C)C(C)(C)O2
• InChI: 1S/C12H24B2O4/c1-9(2)10(3,4)16-13(15-9)14-17-11(5,6)12(7,8)18-14/h1-8H3
• InChI key: IPWKHHSGDUIRAH-UHFFFAOYSA-N

Description

General description

Bis(pinacolato)diboron or (B₂pin₂) is the most commonly used diborane reagent in organic synthesis due to its high stability in air and moisture. It can be synthesized by treating tetrakis(dimethylamino)diboron with pinacol in acidic conditions.

Application

Reagent used for the cis-vicinal diborylation of acetylenes and olefins with Pt catalysis; borylation of aromatics by Pd catalysis.

Substrate used in a new palladium-catalyzed cyclization of 1,6-enynes leading to homoallylic alkylboronates.

Used to construct a tetramethylpyrrolidine nitroxide scaffold for the synthesis of paramagnetic heterocycles by Suzuki coupling.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves