401814-54-8

Basic information

• Product Name: Benzene, 1,1'-[(1E,3E,5E)-3-nitro-1,3,5-hexatriene-1,6-diyl]bis[3-methoxy-
• CAS NO: 401814-54-8
• Molecular Formula: C20H19NO4
• Molecular Weight: 337.375
• Mol File: 401814-54-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1'-[(1E,3E,5E)-3-nitro-1,3,5-hexatriene-1,6-diyl]bis[3-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-[(1E,3E,5E)-3-nitro-1,3,5-hexatriene-1,6-diyl]bis[3-methoxy-(401814-54-8)
• EPA Substance Registry System: Benzene, 1,1'-[(1E,3E,5E)-3-nitro-1,3,5-hexatriene-1,6-diyl]bis[3-methoxy-(401814-54-8)

Safety Data

• Hazardous Substances Data: 401814-54-8(Hazardous Substances Data)

Upstream product

• 26905-40-8 3-methoxybenzylmagnesium chloride 
• 132170-79-7 (1E,3E)-1,4-bis(diethylammino)-2,3-dinitro-1,3-butadiene 

Relevant articles and documents

From 3,4-dinitrothiophene to 1,2-diaryl-4-nitrobenzenes through (E,E,E)-1,6-diaryl-3-nitro-1,3,5-hexatrienes

The reactions between 1,2-bis(diethylamino)-2,3-dinitro-1,3-butadiene, easily obtainable by ring-opening of 3,4-dinitrothiophene with diethylamine, and arylmethylmagnesium chlorides in THF at 0°C furnished good yields of (E,E,E)-1,6-diaryl-3-nitro-1,3,5-hexatrienes. To explain the formation of the hexatrienes, a mechanism is advanced which involves, in particular, tautomerisation of the intermediate 1,6-diaryl-3,4-dinitro-2,4-hexadienes followed by base-induced elimination of nitrous acid. The electrocyclic disrotatory conversion of the hexatrienes into the corresponding 5,6-diaryl-2-nitro-1,3-cyclohexadienes was analysed by 1H NMR spectroscopy and exploited for the high-yielding synthesis of 1,2-diaryl-4-nitrobenzenes employing, as oxidants, either DDQ or iodine in the presence of cyclohexene oxide as HI scavenger.