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Key Documents

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:
Molecular Weight:
168.04
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

104.0 °F

Flash Point(C)

40 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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

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