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Sigma-Aldrich

Potassium cyclopropyltrifluoroborate

≥99%

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About This Item

Empirical Formula (Hill Notation):
C3H5BF3K
CAS Number:
1065010-87-8
Molecular Weight:
147.98
MDL number:
MFCD09265031
UNSPSC Code:
12352103
PubChem Substance ID:
24884175
NACRES:
NA.22

Assay

≥99%

form

powder

mp

348-350 °C

SMILES string

[K+].F[B-](F)(F)C1CC1

InChI

1S/C3H5BF3.K/c5-4(6,7)3-1-2-3;/h3H,1-2H2;/q-1;+1

InChI key

CFMLURFHOSOXRC-UHFFFAOYSA-N

General description

May contain 5-10% cyclopropylboronic acid

Application

Organotrifluoroborate involved in Suzuki-Miyaura cross-coupling reactions

Organotrifluoroborates as versatile and stable boronic acid surrogates.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360FD

Hazard Classifications

Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Charette, A. B. et al.
Synlett, 1779-1779 (2005)
Guo-Hua Fang et al.
Organic letters, 6(3), 357-360 (2004-01-30)
[reaction: see text] Stereospecific cyclopropanation of alkenylboronic esters of pinacol followed by in situ treatment with excess KHF(2) afforded the corresponding potassium cyclopropyl trifluoroborates in high yields, which then underwent Suzuki-Miyaura cross-coupling reactions with aryl bromides to give cyclopropyl-substituted arenes

Articles

Potassium Organotrifluoroborates

These bench stable Potassium Organotrifluoroborates are useful for Suzuki-Miyaura cross-coupling reactions and have also been used for a variety of other C-C bond forming reactions. Importantly, these reagents are compatible with a wide range of functional groups and are stable to many commonly used and harsh reaction conditions.

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