180140-09-4

Basic information

• Product Name: (E)-N,N'-Bis-(4-bromo-phenyl)-1,2-dichloro-N,N'-dimethyl-ethene-1,2-diamine
• Synonyms: (E)-N,N'-Bis-(4-bromo-phenyl)-1,2-dichloro-N,N'-dimethyl-ethene-1,2-diamine
• CAS NO: 180140-09-4
• Molecular Weight: 465.015
• Mol File: 180140-09-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (E)-N,N'-Bis-(4-bromo-phenyl)-1,2-dichloro-N,N'-dimethyl-ethene-1,2-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-N,N'-Bis-(4-bromo-phenyl)-1,2-dichloro-N,N'-dimethyl-ethene-1,2-diamine(180140-09-4)
• EPA Substance Registry System: (E)-N,N'-Bis-(4-bromo-phenyl)-1,2-dichloro-N,N'-dimethyl-ethene-1,2-diamine(180140-09-4)

Safety Data

• Hazardous Substances Data: 180140-09-4(Hazardous Substances Data)

Upstream product

• 35452-54-1 4’-bromo-N-methylformanilide 
• 79-37-8 oxalyl dichloride 

Relevant articles and documents

Carbenes from Vilsmeier reagents by the action of bases in POCl3; The umpolung of Vilsmeier reagents

When para-substituted N-methylformanilides are treated in POCl3 with a base, the corresponding Vilsmeier reagent formed undergoes ready deprotonation to give an amino-chlorocarbene from which a range of products derive; a carba- moyl chloride, N-methylisatins, dimers ? [1,2-dichloro-1,2- bis(N-methyl-N-arylamino)ethenes], trimers ? [5,10-dimethyl- 11-(N-methyl-N-arylamino)-10H-indolo[3,2-b]quinolinium and 5,10-dimethyl-10H-indolo[3,2-b]quinolinium salts] and tetramers ? [1,1′-dimethyl-3,3′-bis(N-methyl-N-arylamino)-2,2-biindolyl] are isolated, depending upon the base used and the para-substituent.

Synthetic applications of aminochlorocarbenes: A two-step conversion of N-methylformanilides into 3-arylamino-2-chloroindoles

The thermal cyclisation of 1,2-diarylamino-1,2-dichloroethenes (dimers of arylaminochlorocarbenes) in DMF affords 3-arylamino-2-chloroindoles in good yields (70-91%).