Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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 Code

12 - Non Combustible Liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service