421-05-6

Usage

InChI:InChI=1/C2ClF2N/c3-2(4,5)1-6

Upstream product

• 545-06-2 trichloroacetonitrile 
• 7664-39-3 hydrogen fluoride 
• 1588-39-2 chloro-difluoro-thioacetyl fluoride 
• 383-62-0 ethyl 2-chloro-2,2-difluoroacetate 
• 354-28-9 2-chloro-2,2-difluoroacetamide 

Downstream Products

• 353-85-5 trifluoroacetonitrile 
• 13337-86-5 2,4,6-tris-(chloro-difluoro-methyl)-2-(4-chloro-phenyl)-1,2-dihydro-[1,3,5]triazine 
• 13337-85-4 2,4-diphenyl-2,6-bis(chlorodifluoromethyl)-1,2-dihydrotriazine 
• 454-58-0 2-Difluorchlormethyl-pyridin 
• 13337-82-1 α-Chlor-α,α-difluor-acetophenon-imin 
• 13337-83-2 2,4,6-tris-(chloro-difluoro-methyl)-2-phenyl-1,2-dihydro-[1,3,5]triazine 
• 14727-31-2 2,4,6-tris-(chloro-difluoro-methyl)-2-(3,4-dichloro-phenyl)-1,2-dihydro-[1,3,5]triazine 

Relevant academic research and scientific papers

Activated dimethyl sulfoxide dehydration of amide and its application to one-pot preparation of benzyl-type perfluoroimidates

Various types of primary amides were treated under an activated dimethyl sulfoxide (DMSO) species, (COCl)2-DMSO and Et3N, as a dehydrating agent to obtain nitriles in excellent yield. This dehydration system was extended to a one-pot preparation of perfluoroimidates via volatile perfluoronitriles from perfluoroamides. Fifteen benzyl-type perfluoroimidates can be prepared in 70-90% yield as more stable imidates than the trichloro analogue. MPM- and DMPM-perfluoroimidates can be used to protect alcohols in place of the trichloroacetimidate with excellent chemical properties and in comparable yields.

Allyl, epoxy and glycosyl perfluoroimidates. One-pot preparation and reaction

The one-pot preparation of allyl, epoxy and glycosyl perfluoroimidates and their reaction are described. Volatile perfluoronitriles were generated from perfluoroamides with an 'activated' dimethyl sulfoxide (DMSO) species at -78°C. Allyl, epoxy and glycosyl perfluoroimidates were prepared in 44-92% yield following in situ nucleophilic addition of alcohol and sugar derivatives to nitriles. The obtained trifluoroacetimidates were more stable than the trichloro analogue and were easily purified by SiO2 column chromatography and/or distillation. The 3,3-sigmatropic rearrangement of allylic analogues, acid-catalyzed cyclization of the epoxy analogues and glycosylation of sugar analogues were studied comparing with their corresponding trichloroacetimidates. The trifluoroacetimidates were considerably less reactive than trichloroacetimidates due to their electron-withdrawing substituents on the imidate carbon.