364-94-3

Basic information

• Product Name: N,N-DIETHYL CHLOROFLUOROACETAMIDE
• Synonyms: N,N-DIETHYL CHLOROFLUOROACETAMIDE;N1,N1-Diethyl-2-chloro-2-fluoroacetamide;2-Chloro-N,N-diethyl-2-fluoroacetamide
• CAS NO: 364-94-3
• Molecular Formula: C₆H₁₁ClFNO
• Molecular Weight: 167.61
• Mol File: 364-94-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 55 °C
• Flash Point: 80.8 °C
• Appearance: /
• Density: 1.123 g/cm³
• Vapor Pressure: 0.197mmHg at 25°C
• Refractive Index: 1.43
• CAS DataBase Reference: N,N-DIETHYL CHLOROFLUOROACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIETHYL CHLOROFLUOROACETAMIDE(364-94-3)
• EPA Substance Registry System: N,N-DIETHYL CHLOROFLUOROACETAMIDE(364-94-3)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 364-94-3(Hazardous Substances Data)

Usage

General Description

N,N-Diethyl chlorofluoroacetamide is a synthetic chemical compound commonly used as an insect repellent and as a defense against potential attacks from humans and animals. It is known for its powerful and persistent effects as a repellent, making it a popular choice for use in outdoor activities such as camping and hiking. The compound is also used in some commercial applications, such as a component of certain household pest control products. However, due to its potential toxicity and environmental impact, the use of N,N-Diethyl chlorofluoroacetamide is regulated in many countries, and alternative, more environmentally friendly repellents are being researched and developed.

InChI:InChI=1/C6H11ClFNO/c1-3-9(4-2)6(10)5(7)8/h5H,3-4H2,1-2H3

Upstream product

• 357-83-5 N-(2-chloro-1,1,2-trifluoroethyl)diethylamine 
• 71-36-3 butan-1-ol 
• 87651-34-1 pentachloro-2-(trimethylsiloxy)propene 
• 857899-86-6 (1-hydrohexafluoroisobutenyloxy)trimethylsilane 
• 67406-60-4 2,2-dichloro-1,1-difluoroethyldiethylamine 

Relevant articles and documents

Reaction of 1-hydrohexafluoroisobutenyloxytrimethylsilane with fluoride ion sources. 2,2,2′,2′-Tetrakis(trifluoromethyl)divinyl ether

The reaction of 1-hydrohexafluoroisobutenyloxytrimethylsilane (2a) with cesium fluoride in diglyme leads to elimination of trimethylfluorosilane to form the 1-hydrohexafluoroisobutenolate anion (3), which is silylated with trialkylchlorosilanes at the oxygen atom. In the presence of bis(trifluoromethyl)ketene N,N,O-trimethylaminoacetal or N-(α,α- difluoroalkyl)-dialkylamines, silane 2a is transformed into 2,2,2′, 2′-tetrakis(trifluoromethyl)divinyl ether. The reaction of trifluoroacetic anhydride with N-(1,1,2,2-tetrafluoroethyl)diethylamine affords trifluoroacetyl fluoride in quantitative yield.

TRANSFORMATION OF CHLOROFLUOROETHYLDIETHYLAMINES TO N,N-DIETHYLDIFLUOROACETAMIDE

Hydrolysis of 2-chloro-1,1,2-trifluoroethyldiethylamine (I) and 2,2-dichloro-1,1-difluoroethyldiethylamine (II) in the presence of triethylamine afforded N,N-diethylchlorofluoroacetamide (VII) and N,N-diethyldichloroacetamide (VIII), respectively.Triethylamine hydrofluoride, arising in the reaction, was used for fluorination and transformation of the amides VII and VIII to N,N-diethyldifluoroacetamide (VI).The C-Cl bond of the CHClF group in VII proved to be more reactive in nucleophilic substitution with fluoride ion than the corresponding bond in the CHCl2 group of VIII.