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790877

Sigma-Aldrich

Tris(2,2,2-trifluoroethyl) borate

97%

Synonym(s):

Tris(2,2,2-trifluoroethyl)borate, Sheppard Amidation Reagent, Tris(2,2,2-trifluoroethoxy)boron, Sheppard Reagent

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About This Item

Empirical Formula (Hill Notation):
C6H6BF9O3
CAS Number:
659-18-7
Molecular Weight:
307.91
MDL number:
MFCD00093768
UNSPSC Code:
12352103
PubChem Substance ID:
329768246
NACRES:
NA.22

Quality Level

100

assay

97%

form

liquid

refractive index

n/D 1.298 (lit.)

density

1.430 g/mL at 25 °C

SMILES string

FC(F)(F)COB(OCC(F)(F)F)OCC(F)(F)F

InChI

1S/C6H6BF9O3/c8-4(9,10)1-17-7(18-2-5(11,12)13)19-3-6(14,15)16/h1-3H2

InChI key

DIEXQJFSUBBIRP-UHFFFAOYSA-N

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Application

Reagent can promote the direct formation of amides from carboxylic acids and amines under thermal and microwave conditions.

pictograms

Flame
GHS02

signalword

Warning

hcodes

H226

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

109.9 °F

flash_point_c

43.3 °C

Certificates of Analysis (COA)

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Rachel M Lanigan et al.
The Journal of organic chemistry, 78(9), 4512-4523 (2013-04-17)
B(OCH2CF3)3, prepared from readily available B2O3 and 2,2,2-trifluoroethanol, is as an effective reagent for the direct amidation of a variety of carboxylic acids with a broad range of amines. In most cases, the amide products can be purified by a
Pavel Starkov et al.
Organic & biomolecular chemistry, 9(5), 1320-1323 (2011-01-08)
Simple borates serve as effective promoters for amide bond formation with a variety of carboxylic acids and amines. With trimethyl or tris(2,2,2-trifluoroethyl) borate, amides are obtained in good to excellent yield and high purity after a simple work-up procedure. Tris(2,2,2-trifluoroethyl)

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