529907

(E)-1-Pentene-1,2-diboronic acid bis(pinacol) ester

• Synonym(s): 1-[cis-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)] pentene, 2,2′-[(1Z)-1-Propyl-1,2-ethenediyl]bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane]
• Empirical Formula (Hill Notation): C₁₇H₃₂B₂O₄
• CAS Number: 307531-75-5
• Molecular Weight: 322.06
• MDL number: MFCD03093909
• UNSPSC Code: 12352103
• PubChem Substance ID: 24877718
• NACRES: NA.22

Properties

• refractive index: n20/D 1.455 (lit.)
• bp: 301-303 °C (lit.)
• density: 0.954 g/mL at 25 °C (lit.)
• SMILES string: CCC\C(=C\B1OC(C)(C)C(C)(C)O1)B2OC(C)(C)C(C)(C)O2
• InChI: 1S/C17H32B2O4/c1-10-11-13(19-22-16(6,7)17(8,9)23-19)12-18-20-14(2,3)15(4,5)21-18/h12H,10-11H2,1-9H3/b13-12-
• InChI key: MXQDNQSRLNMUOP-SEYXRHQNSA-N

Description

General description

(E)-1-Pentene-1,2-diboronic acid bis(pinacol) ester is an alkenyl boronate ester that can be utilized for Suzuki-Miyaura cross-coupling reaction. Boronate esters are air- and chromatography-stable.

Application

(E)-1-Pentene-1,2-diboronic acid bis(pinacol) ester can be used as a reactant in the stereoselective synthesis of γ-boryl substituted homoallylic alcohols by reacting with aromatic aldehydes via Ru-catalyzed double bond transposition reaction.

Safety Information

• Storage Class: 10 - Combustible liquids not in Storage Class 3
• wgk_germany: WGK 3
• flash_point_f: 169.0 °F - closed cup
• flash_point_c: 76.1 °C - closed cup
• ppe: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)