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Merck
CN

803774

Colby trifluoromethylation reagent

Synonym(s):

Hexafluoroacetone hydrate-1,8-diazo-bicyclo[5.4.0]undec-7-ene salt

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About This Item

Empirical Formula (Hill Notation):
C12H18F6N2O2
CAS Number:
1400691-55-5
Molecular Weight:
336.27
UNSPSC Code:
12352101

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SMILES string

OC([O-])(C(F)(F)F)C(F)(F)F.C1CCC2=[N+](CC1)CCCN2

form

solid

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Application

Colby trifluoromethylation reagent may be used for the preparation of fluorinated organic compounds.
The Colby Trifluoromethylation Reagent is an air-stable, white solid, which can be used as a source of fluoroform through the release of trifluoroacetate. This reagent can add trifluoromethyl groups in a nucleophlic fashion to carbonyls and sulfides.

General description

Colby trifluoromethylation reagent is an amidinate salt of hexafluoroacetone hydrate. This reagent can be prepared from the ethereal solution of hexafluoroacetone trihydrate. It undergoes various trifluoromethylation reactions with electrophiles under different reaction conditions to afford trifluoromethylated products.

Other Notes

Amidinate Salt of Hexafluoroacetone Hydrate for the Preparation of Fluorinated Compounds by the Release of Trifluoroacetate

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

hcodes

H302,H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Mark V Riofski et al.
Organic letters, 15(1), 208-211 (2012-12-18)
A powerful, new reagent, an amidinate salt of hexafluoroacetone hydrate, is an air-stable salt that can be used for the preparation of fluorinated organic molecules. Nucleophilic trifluoromethylation reactions are demonstrated following the base-promoted release of trifluoroacetate. This reagent is soluble

Related Content

Colby Group – Professor Product Portal

Prof. David Colby's laboratory is developing synthetic methods to enable the efficient modification of complex molecules, such as natural products, as well as the production of fluorinated compounds. They have focused on understanding how to cleave bonds in order to remodel structures, and their first major discovery is that the release of trifluoroacetate is a powerful approach to break carbon–carbon bonds. This strategy has enabled the invention of new reagents and methods for the synthesis of fluorinated products for drug discovery and for exploring medicinal chemistry.

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