33692-24-9

Basic information

• Product Name: Benzenesulfinamide, N,4-dimethyl-N-phenyl-
• CAS NO: 33692-24-9
• Molecular Formula: C14H15NOS
• Molecular Weight: 245.345
• Mol File: 33692-24-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzenesulfinamide, N,4-dimethyl-N-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfinamide, N,4-dimethyl-N-phenyl-(33692-24-9)
• EPA Substance Registry System: Benzenesulfinamide, N,4-dimethyl-N-phenyl-(33692-24-9)

Safety Data

• Hazardous Substances Data: 33692-24-9(Hazardous Substances Data)

Upstream product

• 6873-55-8 p-tolylsulfinyl amide 
• 100-61-8 N-methylaniline 
• 91378-37-9 S,S-diphenyl-(N-p-tolylfulfinyl)sulfoximine 
• 10439-23-3 4-methylbenzenesulfinyl chloride 

Downstream Products

• 87433-16-7 N-(3-methoxy-2,4,6-trideuteriophenyl)-N-methylheptadeuterio-4-toluenesulfinamide 
• 87433-28-1 3-methoxy-N-methyl-N,2,4,6-tetradeuteroaniline 
• 100-61-8 N-methylaniline 
• 42843-43-6 N-dicyclohexyl-p-toluenesulfinamide 
• 49833-45-6 tert-butyl 4-methylphenyl sulfoxide 
• 30506-35-5 butyl(p-tolyl)sulfoxide 

Relevant articles and documents

Rare-Earth-Catalyzed Transsulfinamidation of Sulfinamides with Amines

A rare-earth-catalyzed transsulfinamidation of primary sulfinamides with alkyl, aryl, and heterocyclic amines for the synthesis of diverse secondary and tertiary sulfinamides has been realized. Unlike transition metal-catalyzed cross-coupling approaches restricted to non-commercially available disubstituted O-benzoyl hydroxylamines, this newly developed protocol is suitable for diverse readily available primary and secondary amines without any modifications. Excellent catalytic activity and selectivity are achieved with Eu(OTf)3 under mild reaction conditions, which extends the applicability of rare-earth catalysis.

Substitution at Tricoordinate Sulfur(IV). Rearrangement of Sulfinanilides to Anilino Sulfoxides

Seven N-methyl-N-aryl-p-toluenesulfinamides (1, 3-Me2NC6H4; 2, 3-MeOC6H4; 3, 4-MeOC6H4; 4, 3-MeC6H4; 5, Ph; 6, 3-ClC6H4; 7, 3-FC6H4), N-(3-methoxyphenyl)-p-toluenesulfinamide (8), and two N-methyl-N-aryl-methanesulfinamides (9, 3-Me2NC6H4; 10, 3-MeOC6H4) were prepared from the corresponding sulfinyl chloride and the substituted aniline.Sulfinanilides 2 and 7 were treated with alkyllithiums in vain attempts to induce rearrangement to the diaryl sulfoxides via endocyclic nucleophilic attack by carbon 2 of the aniline ring on sulfur.Instead, the alkyllithium cleaved the S-N bond to yield the aniline and alkyl p-tolyl sulfoxide.Upon treatment with gaseous HCl in chloroform, the sulfinanilides rearranged as follows: 1 gave 4-(dimethylamino)-2-(methylamino)-4'-methyldiphenyl sulfoxide (92percent yield), 2 gave 2-methoxy-4-(methylamino)-4'-methyldiphenyl sulfoxide (26percent yield) and 4-methoxy-2-(methylamino)-4'-methyldiphenyl sulfoxide (70percent yield), 4 gave 2-methyl-4-(methylamino)-4'-methyldiphenyl sulfoxide (71percent yield), 9 gave methyl 4-(dimethylamino)-2-(methylamino)phenylsulfoxide (20percent yield), and 10 gave methyl 2-methoxy-4-(methylamino)phenyl sulfoxide (5percent yield).Sulfinanilides 3 and 5-8 did not rearrange.A tentative mechanism for the rearrangement is proposed.