105973-44-2

Basic information

• Product Name: N,N-dimethyl-3-(o-tolyl)propanamide
• Synonyms: N,N-dimethyl-3-(o-tolyl)propanamide
• CAS NO: 105973-44-2
• Molecular Weight: 191.273
• Mol File: 105973-44-2.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: N,N-dimethyl-3-(o-tolyl)propanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-dimethyl-3-(o-tolyl)propanamide(105973-44-2)
• EPA Substance Registry System: N,N-dimethyl-3-(o-tolyl)propanamide(105973-44-2)

Safety Data

• Hazardous Substances Data: 105973-44-2(Hazardous Substances Data)

Upstream product

• 201230-82-2 carbon monoxide 
• 611-15-4 1-methyl-2-vinyl-benzene 
• 68-12-2 N,N-dimethyl-formamide 
• 127-19-5 N,N-dimethyl acetamide 
• 89-95-2 2-methyl-benzyl alcohol 
• 95-49-8 2-methylchlorobenzene 

Relevant articles and documents

Iridium-catalyzed selective α-alkylation of unactivated amides with primary alcohols

The first α-alkylation of unactivated amides with primary alcohols is described. An effective and robust iridium pincer complex has been developed for selective α-alkylation of tertiary and secondary acetamides involving a borrowing hydrogen methodology. The method is compatible with alcohols bearing various functional groups. This presents a convenient and environmentally benign protocol for α-alkylation of amides.

Radical condensation between benzylic alcohols and acetamides to form 3-arylpropanamides

A new radical condensation reaction is developed where benzylic alcohols and acetamides are coupled to generate 3-arylpropanamides with water as the only byproduct. The transformation is performed with potassium tert-butoxide as the only additive and gives rise to a variety of 3-arylpropanamides in good yields. The mechanism has been investigated experimentally with labelled substrates, trapping experiments and spectroscopic measurements. The findings indicate a radical pathway where potassium tert-butoxide is believed to serve a dual role as both base and radical initiator. The radical anion of the benzylic alcohol is proposed as the key intermediate, which undergoes coupling with the enolate of the amide to form the new C-C bond. Subsequent elimination to the corresponding cinnamamide and olefin reduction then affords the 3-arylpropanamides.

Manganese-catalyzed direct C-C coupling of α-C-H bonds of amides and esters with alcohols: Via hydrogen autotransfer

Herein we report an efficient manganese-catalyzed C-alkylation of unactivated amides and tert-butyl acetate using alcohols as alkylating agents. This elegant approach exhibits a broad substrate scope providing the C-C coupled products of amides via a hydrogen auto-transfer strategy using aryl, heteroaryl, and aliphatic alcohols.