473294

Bis(pinacolato)diboron

99%

• Synonyme(s) : 4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi-1,3,2-dioxaborolane
• Formule empirique (notation de Hill): C₁₂H₂₄B₂O₄
• Numéro CAS: 73183-34-3
• Poids moléculaire : 253.94
• Numéro MDL: MFCD00799570
• Code UNSPSC : 12352103
• ID de substance PubChem : 24870893
• Nomenclature NACRES : NA.22

Propriétés

• Pureté: 99%
• Forme: powder (or crystals)
• Pf: 137-140 °C (lit.)
• Chaîne SMILES: 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
• Clé InChI: IPWKHHSGDUIRAH-UHFFFAOYSA-N

Description

Description générale

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.

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type N95 (US)