54874-31-6

Basic information

• Product Name: 1,4-dimethyl-c-4-nitrocyclohexa-2,5-dien-r-1-yl acetate
• Synonyms: 1,4-dimethyl-c-4-nitrocyclohexa-2,5-dien-r-1-yl acetate
• CAS NO: 54874-31-6
• Molecular Weight: 211.218
• Mol File: 54874-31-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,4-dimethyl-c-4-nitrocyclohexa-2,5-dien-r-1-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-dimethyl-c-4-nitrocyclohexa-2,5-dien-r-1-yl acetate(54874-31-6)
• EPA Substance Registry System: 1,4-dimethyl-c-4-nitrocyclohexa-2,5-dien-r-1-yl acetate(54874-31-6)

Safety Data

• Hazardous Substances Data: 54874-31-6(Hazardous Substances Data)

Upstream product

• 54913-24-5 (Z)-1,4-dimethyl-4-nitrocyclohexa-2,5-dienol 
• 75-36-5 acetyl chloride 
• 106-42-3 para-xylene 
• 108-24-7 acetic anhydride 

Downstream Products

• 54874-35-0 (E)-1,4-dimethyl-4-nitrocyclohexa-2,5-dienyl methyl ether 
• 54874-34-9 (Z)-1,4-dimethyl-4-nitrocyclohexa-2,5-dienyl methyl ether 
• 54913-24-5 (Z)-1,4-dimethyl-4-nitrocyclohexa-2,5-dienol 
• 74492-13-0 3-Ethoxy-3,6-dimethyl-6-nitro-cyclohexa-1,4-diene 
• 74492-12-9 3-Ethoxy-3,6-dimethyl-6-nitro-cyclohexa-1,4-diene 
• 78024-94-9 (Z)-2,6-dideuterio-1,4-dimethyl-4-nitrocyclohexa-2,5-dienyl acetate 
• 74492-17-4 3-Allyloxy-3,6-dimethyl-6-nitro-cyclohexa-1,4-diene 
• 74492-16-3 3-Allyloxy-3,6-dimethyl-6-nitro-cyclohexa-1,4-diene 
• 106-42-3 para-xylene 
• 877-48-5 2,5-dimethylphenyl acetate 
• 29559-27-1 1-methyl-4-(nitromethyl)benzene 
• 89-58-7 mononitro-p-xylene 
• 133205-72-8 3,6-dimethyl-t-5-nitrato-r-3,c-4,t-6-trinitrocyclohexene 
• 133205-72-8 3,6-dimethyl-c-5-nitrato-r-3,t-4,c-6-trinitrocyclohexene 

Relevant articles and documents

Ipso Nitration. Solvolytic Behavior of 1,4-Dimethyl-4-nitrohexadienyl Acetate and 1,4-Dimethyl-4-nitrocyclohexadienol

The solvolytic rearomatizations of the E and Z isomers of 1,4-dimethyl-4-nitrocyclohexadienyl acetate (1) have been examined in aqueous ethanol and in sulfuric acid solutions.Solvolysis of 1 in aqueous ethanol involves the elimination of nitrous acid and the migration of the acetoxyl group to yield 2,5-dimethylphenyl acetate.The kinetic behavior of this solvolytic reaction parallels that of the secondary adduct 4-nitro-3,4,5-trimethylcyclohexadienyl acetate (2).No kinetic isotope effects were detected when 1,4-dimethyl-4-nitrocyclohexadienyl-2,3,5,6-d4 acetate (1-d4) or 1,4-dimethyl-4-nitrocyclohexadienyl-Me-d6 (1-d6) were used as substrates.The collected data suggest a rate-limiting loss of nitrile ion from 1 followed by migration of the acetoxyl group and proton loss.The behavior of Z and E isomers of 1,4-dimethyl-4-nitrocyclohexadienol (3) in aqueous ethanol differs from that of 1 in several ways.The major product of solvolysis is 2,4-dimethylphenol.The rates of solvolysis of the stereoisomers of 3 do not differ appreciably one from another, and the spectral yield is only 30-40percent of that anticipated.These differences are taken to reflect a rate-limiting migration in the solvolysis of 3 rather than a rate-limiting loss of nitrate ion.Solvolysis of 1 in greater than 77percent sulfuric acid gives 1,4-dimethyl-2-nitrobenzene in quantitative yield.The yield of nitro aromatic falls off smoothly as the acid concentration is lowered toward 50percent.Within the 70-50percent acid range, the yield of side-chain substitution products appears to increase, hold roughly constant, and then decrease.Larger yields of nitro aromatic and smaller yields of side-chain substitution product are found when 1-d6 is used as a reactant.The solvolyses in strong acids are discussed in terms of re-formation of the ipso ion and subsequent partitioning.