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MilliporeSigma

790877

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

Key Documents

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Quality Level

100

assay

97%

form

liquid

refractive index

n/D 1.298 (lit.)

density

1.430 g/mL at 25 °C

functional group

fluoro

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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Tris(2,2,2-trifluoroethyl) borate 97%

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Sigma-Aldrich

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Tris(trimethylsilyl) borate

2,2,2-Trifluoroethyl trifluoromethanesulfonate 95%

Sigma-Aldrich

752924

2,2,2-Trifluoroethyl trifluoromethanesulfonate

Bis(2,2,2-trifluoroethyl) ether 98%

Sigma-Aldrich

287571

Bis(2,2,2-trifluoroethyl) ether

assay

97%

assay

99%

assay

95%

assay

98%

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

refractive index

n/D 1.298 (lit.)

refractive index

n20/D 1.386 (lit.)

refractive index

n20/D 1.306

refractive index

n20/D 1.300 (lit.)

form

liquid

form

liquid

form

liquid

form

liquid

density

1.430 g/mL at 25 °C

density

0.831 g/mL at 25 °C (lit.)

density

1.611 g/mL at 25 °C

density

1.404 g/mL at 25 °C (lit.)

functional group

fluoro

functional group

-

functional group

fluoro, triflate

functional group

ether, fluoro

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ8389
MKCS2757
MKCP4222
MKCN0097
MKCL7393

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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)
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

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