87433-28-1

Basic information

• Product Name: 3-methoxy-N-methyl-N,2,4,6-tetradeuteroaniline
• Synonyms: 3-methoxy-N-methyl-N,2,4,6-tetradeuteroaniline
• CAS NO: 87433-28-1
• Molecular Weight: 141.15
• Mol File: 87433-28-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-methoxy-N-methyl-N,2,4,6-tetradeuteroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methoxy-N-methyl-N,2,4,6-tetradeuteroaniline(87433-28-1)
• EPA Substance Registry System: 3-methoxy-N-methyl-N,2,4,6-tetradeuteroaniline(87433-28-1)

Safety Data

• Hazardous Substances Data: 87433-28-1(Hazardous Substances Data)

Upstream product

• 33692-24-9 N-Methyl-N-phenyl-p-toluolsulfinamid 
• 100-61-8 N-methylaniline 

Downstream Products

• 87433-16-7 N-(3-methoxy-2,4,6-trideuteriophenyl)-N-methylheptadeuterio-4-toluenesulfinamide 

Relevant articles and documents

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.