1737-07-1

Basic information

• Product Name: N-tosyl 2,2,2-trifluoroacetaldimine
• CAS NO: 1737-07-1
• Molecular Weight: 251.229
• Mol File: 1737-07-1.mol

Chemical Properties

• CAS DataBase Reference: N-tosyl 2,2,2-trifluoroacetaldimine(CAS DataBase Reference)
• NIST Chemistry Reference: N-tosyl 2,2,2-trifluoroacetaldimine(1737-07-1)
• EPA Substance Registry System: N-tosyl 2,2,2-trifluoroacetaldimine(1737-07-1)

Safety Data

• Hazardous Substances Data: 1737-07-1(Hazardous Substances Data)

Upstream product

• 75-90-1 2,2,2-Trifluoroacetaldehyde 
• 70-55-3 toluene-4-sulfonamide 

Downstream Products

• 235418-59-4 N-<1-(trifluoromethyl)-3-undecenyl>tosylamide 
• 1415638-74-2 N-(1,1,1-trifluoro-6-phenylhexa-3,5-diyn-2-yl)-4-methylbenzenesulfonamide 
• 235418-60-7 N-<4-phenyl-1-(trifluoromethyl)-3-butenyl>tosylamide 

Relevant articles and documents

Synthesis of organofluorine compounds using ene type reaction of N-(p-toluenesulfonyl)trifluoroacetaldehyde imine

N-Tosyltrifluoroacetaldehyde imine (4) reacted as an enophile, but it is very sensitive to moisture and the yields of ene products were low. N-(2,2,2-Trifluoro-1-ethoxyethyl)tosylamide (11), obtained by the reaction of trifluoroacetaldehyde ethyl hemiacetal (1) with tosylamide (3) in the presence of TiCl4 followed by addition of ethanol, was found to react as a good substitute for 4 to give the same products from the ene reaction of 4 in much better yields.

Alkenyl Exchange of Allylamines via Nickel(0)-Catalyzed C-C Bond Cleavage

A functional group exchange reaction between allylamines and alkenes via nickel-catalyzed C - C bond cleavage and formation was developed. This reaction provides a novel protocol, which does not require the use of unstable imine substrates, for the synthesis of allylamines, which are widely used in the production of fine chemicals, pharmaceuticals, and agrochemicals.

Synthesis of organofluorine compounds using the ene reaction of N-(p- toluenesulfonyl)trifluoroacetaldehyde imine

N-Tosyltrifluoroacetaldehyde imine (4) reacted with terminal olefins by only heating together to give the ene reaction products. This means the imine is much more reactive than trifluoroacetaldehyde (2) itself as an enophile. However, 4 was very sensitive to moisture and the yields were low even if it was used without isolation. Further, it did not react with non-terminal olefins. In the course on study of the mechanism of this reaction, we found that N-(2,2,2-trifluoro-1-ethoxyethyl)tosylamide (12), obtained by the reaction of trifluoroacetaldehyde ethyl hemiacetal (1) with tosylamide (3) in the presence of titanium(IV) chloride followed by addition of ethanol, reacted in the presence of sodium hydride and titanium(IV) chloride to give the same products from the ene reaction of 4 in much better yields. Interestingly, this reaction proceeded with non-terminal olefins.