77815-19-1

Basic information

• Product Name: 2,4-dimethyl-4-nitrocyclohexa-2,5-dienone
• Synonyms: 2,4-dimethyl-4-nitrocyclohexa-2,5-dienone
• CAS NO: 77815-19-1
• Molecular Weight: 167.164
• Mol File: 77815-19-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2,4-dimethyl-4-nitrocyclohexa-2,5-dienone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dimethyl-4-nitrocyclohexa-2,5-dienone(77815-19-1)
• EPA Substance Registry System: 2,4-dimethyl-4-nitrocyclohexa-2,5-dienone(77815-19-1)

Safety Data

• Hazardous Substances Data: 77815-19-1(Hazardous Substances Data)

Upstream product

• 509-14-8 tetranitromethane 
• 6738-23-4 2,4-dimethylanisole 
• 105-67-9 2,4-Xylenol 
• 77815-20-4 4,6-dimethyl-6-nitrocyclohexa-2,4-dienone 

Downstream Products

• 13287-32-6 2,4-Dimethyl-4-nitrophenylacetat 
• 14452-34-7 2,4-dimethyl-6-nitrophenol 

Relevant articles and documents

Photochemical nitration by tetranitromethane. Part XXXVII. Adduct formation and the regiochemistry of attack of trinitromethanide ion on radical cations in the photochemical reactions of 2-methyl-, 2,3-dimethyl- and 2,4-Dimethylanisoles

The photolysis of the charge transfer (CT) complex of tetranitromethane and 2-methylanisole 2 in dichloromethane at 20 °C gives the epimeric 1-methoxy-6-methyl-6-nitro-3-trinitromethylcyclohexa-1,4-dienes 8 and 9 in addition to 2-methyl-4-trinitromethylanisole (3) and 2-methyl-4-nitroanisole (4). In acetonitrile the yields of compound 4 and adducts 8 and 9 are significantly higher. Similar reaction of 2,3-dimethylanisole (6) in dichloromethane gave nitro-trinitromethyl adducts 10 and 11, hydroxy-trinitromethyl adducts 12 and 13, 2,3-dimethyl-5-trinitromethylanisole (14), 4-methoxy-2,3-dimethylbenzonitrile N-oxide (15), 2,3-dimethyl-4-trinitromethylanisole (16), 2,3-dimethyl-4-nitroanisole (17), 2,3-dimethyl-4,6-dinitrophenol (18), 3-methoxy-4,5-dimethyl-benzoic acid (19) and the hydroxy dinitro compound (20). The photolysis of the CT complex of 2,4-dimethylanisole (7) with tetranitromethane in dichloromethane gave the epimeric 1-methoxy-4,6-dimethyl-6-nitro-3-trinitromethylcyclohexa-1,4-dienes 21 and 22, together with 4,6-dimethyl-3-trinitromethylanisole (23), 4,6-dimethyl-2-nitrophenol (24), 4,6-dimethyl-2-trinitromethylanisole (25), 4,6-dimethyl-3-nitroanisole (26), 4,6-dimethyl-2-nitroanisole (27) and 4,6-dimethyl-4-nitrocyclohexa-2,5-dienone (28). The modes of formation of the above products are discussed, including the effects of the reaction solvent on those processes. The X-ray crystal structure of 1-methoxy-2-methyl-c-6-nitro-r-3-trinitromethylcyclohexa-1,4-diene (9) is reported. Acta Chemica Scandinavica 1997.

ipso Nitration. XXIV. Nitration of 2-methylphenols. Formation and rearrangement of 6-methyl-6-nitrocyclohexa-2,4-dienones

Nitration of o-cresol and some mono-, di-, and trimethyl derivatives in acetic anhydride at -60 deg C gives 6-methyl-6-nitrocyclohexa-2,4-dienones.The dienones are more labile than the isomeric 4-methyl-4-nitrocyclohexa-2,5-dienones and, if the 2-position of the dienone is not blocked, undergo regiospecific rearrangement to 6-nitro-o-cresols. 2,3,6-Trimethyl- and 2,3,5,6-tetramethylphenol also give a 2,5-dienone with nitro attached to a secondary carbon.