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659851

Sigma-Aldrich

Cyclopropylboronic acid pinacol ester

96%

Synonym(s):

2-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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About This Item

Empirical Formula (Hill Notation):
C9H17BO2
CAS Number:
126689-01-8
Molecular Weight:
168.04
MDL number:
MFCD05663847
UNSPSC Code:
12352103
PubChem Substance ID:
24884163

Quality Level

100

assay

96%

refractive index

n20/D 1.433

bp

146 °C

density

0.922 g/mL at 25 °C

SMILES string

CC1(C)OB(OC1(C)C)C2CC2

InChI

1S/C9H17BO2/c1-8(2)9(3,4)12-10(11-8)7-5-6-7/h7H,5-6H2,1-4H3

InChI key

XGBMQBPLWXTEPM-UHFFFAOYSA-N

Related Categories

Application

Cyclopropylboronic acid pinacol ester can be used:
  • As a cyclopropylating reagent in the study of thiophenol S-cyclopropylation, catalyzed by copper(II) acetate.
  • In one of the key synthetic steps for the preparation of 5-lipoxygenase activating protein (FLAP) inhibitor.

pictograms

Flame
GHS02

signalword

Warning

hcodes

H226

pcodes

P210

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

104.0 °F

flash_point_c

40 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Keith R Fandrick et al.
The Journal of organic chemistry, 80(3), 1651-1660 (2015-01-07)
A practical sequence involving a noncryogenic stereospecific boronate rearrangement followed by a robust formylation with an in situ generated DCM anion has been developed for the asymmetric construction of an all-carbon quaternary stereogenic center of a FLAP inhibitor. The key
Emeline Benoit et al.
Beilstein journal of organic chemistry, 15, 1162-1171 (2019-07-12)
The copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid is reported. The procedure operates under simple conditions to afford the corresponding aryl cyclopropyl sulfides in moderate to excellent yields. The reaction tolerates substitution in ortho-, meta- and para-substitution as well as

Articles

Boronic Acid Esters

The synthesis of biaryl compounds via the Suzuki–Miyaura coupling reaction has become more commonplace now that many arylboronic acids are readily available.

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