659851
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
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
Product Name
Cyclopropylboronic acid pinacol ester, 96%
InChI
1S/C9H17BO2/c1-8(2)9(3,4)12-10(11-8)7-5-6-7/h7H,5-6H2,1-4H3
SMILES string
CC1(C)OB(OC1(C)C)C2CC2
InChI key
XGBMQBPLWXTEPM-UHFFFAOYSA-N
assay
96%
refractive index
n20/D 1.433
bp
146 °C
density
0.922 g/mL at 25 °C
Quality Level
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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.
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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
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