570214

trans-2-Phenylvinylboronic acid pinacol ester

• Synonym(s): (E)-4,4,5,5-Tetramethyl-2-(2-phenylvinyl)-1,3,2-dioxaborolane, (E)-4,4,5,5-Tetramethyl-2-styryl-1,3,2-dioxaborolane, 4,4,5,5-Tetramethyl-2-((E)-2-phenylethenyl)-1,3,2-dioxaborolane, trans-2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)styrene, trans-2-Styreneboronic acid pinacol ester
• Linear Formula: C₆H₅CH=CHBO₂C₂(CH₃)₄
• CAS Number: 83947-56-2
• Molecular Weight: 230.11
• MDL number: MFCD03453666
• UNSPSC Code: 12352103
• PubChem Substance ID: 24880535
• NACRES: NA.22

Properties

• mp: 27-33 °C (lit.)
• SMILES string: [H]\C(B1OC(C)(C)C(C)(C)O1)=C(\[H])c2ccccc2
• InChI: 1S/C14H19BO2/c1-13(2)14(3,4)17-15(16-13)11-10-12-8-6-5-7-9-12/h5-11H,1-4H3/b11-10+
• InChI key: ARAINKADEARZLZ-ZHACJKMWSA-N

Description

Application

Reactant for:

• Oxidative coupling reactions catalyzed by areneruthenium
• Cycloaddition reactions
• Preparation of allyl vinyl ethers via Cu-catalyzed coupling with alcohols
• Preparation of 5-vinyl-3-pyridinecarbonitriles as PKCθ inhibitors
• Diastereoselective addition to zincated hydrazones and stereospecific trapping of boron/zinc bimetallic intermediates by carbon electrophiles
• Regioselective and stereoselective Pd-catalyzed chelate-controlled intermolecular oxidative Heck reactions

Safety Information

• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves