Isopropenylboronic acid pinacol ester

• CAS: 126726-62-3
• Catalog Number: ACM126726623
• Category: Boronic Esters
• Molecular Weight: 168.04g/mol
• Molecular Formula: C9H17BO2
• IUPAC Name: 4,4,5,5-tetramethyl-2-prop-1-en-2-yl-1,3,2-dioxaborolane
• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C(=C)C
• InChI: InChI=1S/C9H17BO2/c1-7(2)10-11-8(3,4)9(5,6)12-10/h1H2,2-6H3
• InChI Key: SVSUYEJKNSMKKW-UHFFFAOYSA-N
• Application: Isopropenylboronic acid pinacol ester serves as a highly versatile reagent in a variety of chemical reactions, including the palladium-catalyzed Suzuki-Miyaura cross-coupling, inverse-electron-demand Diels-Alder reaction, Simmons-Smith cyclopropanation, polyene cyclization, and stereoselective aldol reactions. It is also integral to Grubbs cross-metathesis, intramolecular Suzuki-Miyaura reactions, stereoselective cross-metathesis, dipolar cycloaddition, iodosulfonylation, asymmetric conjugate addition, and intramolecular hydroacylation. Notably, this ester plays a crucial role in the synthesis of therapeutic kinase and enzymatic inhibitors. Its applications extend to serving as an intermediate in the preparation of both cyclic and acyclic organic compounds, and it has been demonstrated that its α-Substituted Allyl/Crotyl variant can achieve highly diastereo- and enantioselective allylboration of aldehydes.
• Complexity: 193
• Covalently-Bonded Unit Count: 1
• Exact Mass: 168.13216g/mol
• Formal Charge: 0
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Heavy Atom Count: 12
• Monoisotopic Mass: 168.13216g/mol
• Rotatable Bond Count: 1