719-11-9

Basic information

• Product Name: 4-methyl-N-(2,2,2-trifluorethyl)benzenesulfonamide
• Synonyms: 4-methyl-N-(2,2,2-trifluorethyl)benzenesulfonamide
• CAS NO: 719-11-9
• Molecular Weight: 253.245
• Mol File: 719-11-9.mol

Chemical Properties

• CAS DataBase Reference: 4-methyl-N-(2,2,2-trifluorethyl)benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methyl-N-(2,2,2-trifluorethyl)benzenesulfonamide(719-11-9)
• EPA Substance Registry System: 4-methyl-N-(2,2,2-trifluorethyl)benzenesulfonamide(719-11-9)

Safety Data

• Hazardous Substances Data: 719-11-9(Hazardous Substances Data)

Upstream product

• 753-90-2 trifluoroethylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 51060-12-9 1-tosyl-2,3-dimethylimidazolium chloride 
• 29981-92-8 1-tosyl-3-methyl-imidazolium chloride 

Relevant articles and documents

NUCLEOPHILIC SUBSTITUTION AT SULFONYL SULFUR ATOM : AMINOLYSIS OF 1-TOSYL-3-METHYL IMIDAZOLIUM CHLORIDE IN AQUEOUS MEDIUM.

Kinetics of the reaction of 1-tosyl-3-methyl-imidazolium chloride with various amines were measured to examine the nature of sulfonyl transfer in enzymatic reactions.The activations parameters and the value of the Broensted exponent, β=0.48, are consistent with a small degree of bonding between the entering amine and the sulfur atom in the transition state.Similarities in the nucleophilic behavior of sulfonyl and carbonyl groups are detected.

From ynamides to highly substituted benzo[b]furans: Gold(I)-catalyzed 5-endo-dig-cyclization/rearrangement of alkylic oxonium intermediates

A series of arylynamides with alkyloxy groups at the ortho position of the aryl group was prepared through a short alkylation/cross-coupling/amidation sequence. The gold-catalyzed conversion of these substrates combined both C-O and C-C formation steps, thus providing benzofurans with amine functionalities at the 2-position and alkyl groups at the 3-position. Cross-over experiments showed that the alkyl-migration step was an intermolecular process. X-ray crystal-structure analysis of two of the products supported our structural assignment. In some cases, the corresponding benzofurans without the alkyl group at the 3-position were obtained as side-products, which were formed through a competing protodeauration process. Golden touch: Arylynamides with o-alkyloxy groups were prepared through an alkylation/cross-coupling/amidation sequence. Their Au-catalyzed conversion provided benzofurans with amine groups at the 2-position and alkyl groups at the 3-position. Copyright

Sulfonyl transfer from imidazoles

The rate constants for the non-catalyzed bimolecular substitution of 1-tosylimidazole, 1, 1-tosyl-3-methylimidazolium, 2, and 1-tosyl-2,3-dimethylimidazolium, 3, chlorides by primary aliphatic amines (5 n Nu=0.5, 0.5 and 0.6 respectively.Despite large variations in the reactivity, 6 powers of ten from 1 to 2, and in the leaving group pK's, 7 units from 2 to 1, the nucleophile effect is found to be nearly constant.The nucleofuge effect is also independent of the nucleophile; apparent βL-coefficients of approximately - 0.9 are observed whatever the amine.These data correspond to rate-limiting transition states where there is small but significant bonding of the sulfonyl with the entering amines and with the leaving imidazoles.These results strongly suggest a concerted single-step displacement mechanism; however, a stepwise mechanism involving a very unstable and very short-lived pentahedric intermediate cannot be strictly ruled out.These findings are compared with those on other acyl transfers.