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681342

Sigma-Aldrich

Potassium (bromomethyl)trifluoroborate

90%

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About This Item

Linear Formula:
BrCH2BF3K
CAS Number:
888711-44-2
Molecular Weight:
200.84
MDL number:
MFCD09265154
UNSPSC Code:
12352103
PubChem Substance ID:
24885633
NACRES:
NA.22

Quality Level

100

assay

90%

form

solid

mp

225-230 °C

functional group

bromo

SMILES string

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

InChI

1S/CH2BBrF3.K/c3-1-2(4,5)6;/h1H2;/q-1;+1

InChI key

AZDFPIRYUOCVCJ-UHFFFAOYSA-N

Application

Organotrifluoroborate involved in:
  • Suzuki-Miyaura cross-coupling reactions
  • Synthesis of functionalized ethyltrifluoroborates
  • SN2 displacement with alkoxides

Organotrifluoroborates as versatile and stable boronic acid surrogates.
Versatile starting material for preparation of a variety of functionalized substrates for Suzuki coupling.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBC7305V
MKBD7450V
MKBD7450
64696DM
MKBB6053

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Gary A Molander et al.
Organic letters, 8(13), 2767-2770 (2006-06-16)
[reaction: see text] We have successfully prepared potassium azidoalkyltrifluoroborates from the corresponding halogen compounds in 94-98% yields through a nucleophilic substitution reaction with NaN(3). In the presence of various alkynes and Cu(I) as a catalyst, these azidotrifluoroborates easily formed 1,4-disubstituted

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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