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529907

Sigma-Aldrich

(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]

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About This Item

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

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

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.[1]

Storage Class Code

10 - Combustible liquids not in Storage Class 3

WGK

WGK 3

Flash Point(F)

169.0 °F - closed cup

Flash Point(C)

76.1 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis of γ-Boryl-Substituted Homoallylic Alcohols with anti Stereochemistry Based on a Double-Bond Transposition
Miura T, et al.
Angewandte Chemie (International ed. in English), 58(4), 1138-1142 (2019)

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