1783-02-4

Basic information

• Product Name: 2,4,6-trimethyl-4-nitrocyclohexa-2,5-dien-1-one
• Synonyms: 2,4,6-trimethyl-4-nitrocyclohexa-2,5-dien-1-one
• CAS NO: 1783-02-4
• Molecular Weight: 181.191
• Mol File: 1783-02-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,4,6-trimethyl-4-nitrocyclohexa-2,5-dien-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-trimethyl-4-nitrocyclohexa-2,5-dien-1-one(1783-02-4)
• EPA Substance Registry System: 2,4,6-trimethyl-4-nitrocyclohexa-2,5-dien-1-one(1783-02-4)

Safety Data

• Hazardous Substances Data: 1783-02-4(Hazardous Substances Data)

Upstream product

• 527-60-6 Mesitol 
• 13021-15-3 2,4,6-trimethyl-N,N-dimethylaniline 

Downstream Products

• 92892-09-6 2,6-dimethyl-4-nitromethyl-phenol 

Relevant articles and documents

The mechanism of nitration of 2,4,6-trialkylphenols by nitrogen dioxide in solution

The apparent rate of reaction of 2,4,6-trialkylphenols with nitrogen dioxide in solution is that of a 6-nitrocyclohexa-2,4-dien-1-one to 4- nitrocyclohexa-2,5-dien-1-one isomerisation unless the 2- and 6-alkyl groups are sufficiently bulky when the rate limiting stage may involve reaction between the appropriate phenoxy radical and NO2.

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.

Isolation and Further Reactions of Charged Species resulting from ipso-attack in the Nitration of Aromatic Amines

Charged species resulting from ipso-attack in the nitration of aromatic amines can be precipitated as hexafluorophosphates but the isolation is complicated by addition and substitution reactions involving water in the solvent.