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665533

Sigma-Aldrich

trans-2-(3-Chlorophenyl)vinylboronic acid pinacol ester

97%

Synonym(s):

2-(E-2-(3-Chlorophenyl)vinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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About This Item

Empirical Formula (Hill Notation):
C14H18BClO2
CAS Number:
871125-84-7
Molecular Weight:
264.56
MDL number:
MFCD08276867
UNSPSC Code:
12352103
PubChem Substance ID:
24884746
NACRES:
NA.22

assay

97%

refractive index

n20/D 1.536

bp

138-140 °C/0.9-1.0 mmHg

density

1.049 g/mL at 25 °C

SMILES string

CC1(C)OB(OC1(C)C)\C=C\c2cccc(Cl)c2

InChI

1S/C14H18BClO2/c1-13(2)14(3,4)18-15(17-13)9-8-11-6-5-7-12(16)10-11/h5-10H,1-4H3/b9-8+

InChI key

NZBKTAJNGYXYSQ-CMDGGOBGSA-N

Application

trans-2-(3-Chlorophenyl)vinylboronic acid pinacol ester can be used as a reactant:
  • To prepare aryl derivatives by C−C bond formation via palladium-catalyzed Suzuki−Miyaura reaction.
  • In the diastereoselective synthesis of alkenes via K3PO4-promoted transition metal-free nucleophilic substitution of unactivated alkyl triflates.
  • To synthesize (3-chlorophenyl)cyclopropyl boronic acid pinacol ester by reacting with diazomethane.

Storage Class

12 - Non Combustible Liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBD1620V
06602PD

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Mild Base Promoted Nucleophilic Substitution of Unactivated sp3-Carbon Electrophiles with Alkenylboronic Acids
Liu Shiwen, et al.
advanced synthesis and catalysis, 360(19), 3667-3671 (2018)
Automated library synthesis of cyclopropyl boronic esters employing diazomethane in a tube-in-tube flow reactor
Koolman HF, et al.
Organic & Biomolecular Chemistry, 14(27), 6591-6595 (2016)
Mild Base Promoted Nucleophilic Substitution of Unactivated sp3-Carbon Electrophiles with Alkenylboronic Acids
Liu Shiwen, et al.
Advanced Synthesis & Catalysis, 360(19), 3667-3671 (2018)

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