193686-80-5

Basic information

• Product Name: 1H-Indole, 2-nitro-1-(phenylsulfonyl)-
• CAS NO: 193686-80-5
• Molecular Formula: C14H10N2O4S
• Molecular Weight: 302.31
• Mol File: 193686-80-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1H-Indole, 2-nitro-1-(phenylsulfonyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 2-nitro-1-(phenylsulfonyl)-(193686-80-5)
• EPA Substance Registry System: 1H-Indole, 2-nitro-1-(phenylsulfonyl)-(193686-80-5)

Safety Data

• Hazardous Substances Data: 193686-80-5(Hazardous Substances Data)

Upstream product

• 98-09-9 benzenesulfonyl chloride 
• 193686-70-3 2-nitroindole 
• 552-89-6 2-nitro-benzaldehyde 
• 16714-25-3 2-azidobenzaldehyde 
• 120-72-9 indole 
• 139409-34-0 2-bromo-1H-indole 
• 40899-71-6 1-benzenesulfonylindole 
• 99275-44-2 2-iodo-1-(phenylsulfonyl)-1H-indole 

Relevant articles and documents

A new synthesis of 2-nitroindoles

The C-2 lithiation of N-Boc- and N-(phenylsulfonyl)indoles (4-7) followed by reaction with dinitrogen tetroxide at low temperature affords the corresponding 2-nitroindoles 10-13 in 63-78% yields. Deprotection of the N-Boc-2-nitroindoles (10, 11) with trifluoroacetic acid gives 2-nitroindole (3) and 3-methyl-2-nitroindole (14) in essentially quantitative yields.

A convenient synthesis of 2-nitroindoles

The reaction of 2-iodo- and 2-bromoindoles with silver nitrite in aqueous acetone affords the corresponding 2-nitroindoles in modest to good yields.

Synthesis of 2-nitroindoles via the Sundberg indole synthesis

A three-step sequence has been developed for converting o-nitrobenzaldehydes into 2-nitroindoles. The key step involves the thermolysis of 2-(o-azidophenyl)nitroethylene (10) in xylenes which gives 2-nitroindole (4) in 54% yield, akin to the classic Sundberg indole synthesis. This procedure has also been utilized to synthesize 5,6-dimethoxy-2-nitroindole (14).