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Merck
CN

804673

Potassium (2-phenylacetyl)trifluoroborate

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经验公式(希尔记法):
C8H7BF3KO
化学文摘社编号:
分子量:
226.05
UNSPSC Code:
12352103
PubChem Substance ID:
MDL number:
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InChI

1S/C8H7BF3O.K/c10-9(11,12)8(13)6-7-4-2-1-3-5-7;/h1-5H,6H2;/q-1;+1

SMILES string

[K+].F[B-](F)(F)C(=O)Cc1ccccc1

InChI key

SEOSMCJOPUBHBF-UHFFFAOYSA-N

form

powder

mp

178-183 °C (d)

functional group

phenyl

General description

Potassium (2-phenylacetyl)trifluoroborate (potassium benzyltrifluoroborate, phenylacetyl trifluoroborate) belongs to the class of compounds known as potassium acyltrifluroborates (KATs). This trifluoroborate salt is stable and does not readily undergo trimerization. It undergoes palladium-catalyzed cross-coupling reaction with p-nitro triflate to form the corresponding biaryl. Phenylacetyl trifluoroborate acts as an acyl donor during the amidation of O-benzoyl hydroxylamine to form the corresponding amide.

Application

Potassium acyltrifluroborates (KATs) are bench, air and moisture stable reagents for rapid chemoselective amide bond formations with hydroxylamines. These amide bond forming reactions proceed under aqueous conditions without the need for coupling reagents or protecting groups. This product was introduced in collaboration with the Bode Research Group.

pictograms

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signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

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分析证书(COA)

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Organotrifluoroborates: Expanding Organoboron Chemistry
Molander GA and Figueroa RF
Aldrichimica Acta, 38(2), 58-58 (2005)
Amide-forming ligation of acyltrifluoroborates and hydroxylamines in water.
Aaron M Dumas et al.
Angewandte Chemie (International ed. in English), 51(23), 5683-5686 (2012-04-28)

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