257953-14-3

Basic information

• Product Name: N-ethyl-2,4-dimethylbenzenesulfonamide
• Synonyms: N-ethyl-2,4-dimethylbenzenesulfonamide
• CAS NO: 257953-14-3
• Molecular Weight: 213.301
• Mol File: 257953-14-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-ethyl-2,4-dimethylbenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-ethyl-2,4-dimethylbenzenesulfonamide(257953-14-3)
• EPA Substance Registry System: N-ethyl-2,4-dimethylbenzenesulfonamide(257953-14-3)

Safety Data

• Hazardous Substances Data: 257953-14-3(Hazardous Substances Data)

Upstream product

• 80-39-7 N-ethyl-4-methyl-benzenesulfonamide 
• 74-88-4 methyl iodide 

Downstream Products

• 92681-07-7 2-Ethyl-5-methyl-3-oxo-benzisothiazolin-1,1-dioxid 
• 257953-00-7 N-ethyl-5-methyl-1,2-benzisothiazoline-3-one-1-oxide 
• 7467-12-1 2,4-dimethylbenzenesulfonamide 

Relevant articles and documents

Selective ortho and benzylic functionalization of secondary and tertiary p-tolylsulfonamides. Ipso-bromo desilylation and Suzuki cross-coupling reactions

Kinetic vs thermodynamic deprotonation studies on secondary and tertiary sulfonamides 1 and 2 using n-BuLi have been carried out. While both 1 and 2 show kinetic ortho-metalation, thermodynamic conditions lead to ortho and benzylic deprotonation, respectively (Figures 1 and 2). Metalation of 1 using the n-BuLi/KOtBu superbase led to regioselective benzylic metalation (Figure 4); LDA deprotonation was also briefly explored. Application of the developed conditions allows the synthesis of diverse sulfonamide products 5a-e, 6a-e, 7a,b, and 8a-e. Ipso-bromo desilylation reactions afford sulfonamides 9a,b while Suzuki cross-coupling reactions furnish biaryl sulfonamides 11a-c.