1665-87-8

Basic information

• Product Name: 2,5-Cyclohexadien-1-one, 2,4,6-tris(1,1-dimethylethyl)-4-nitro-
• CAS NO: 1665-87-8
• Molecular Formula: C18H29NO3
• Molecular Weight: 307.433
• Mol File: 1665-87-8.mol

Chemical Properties

• CAS DataBase Reference: 2,5-Cyclohexadien-1-one, 2,4,6-tris(1,1-dimethylethyl)-4-nitro-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Cyclohexadien-1-one, 2,4,6-tris(1,1-dimethylethyl)-4-nitro-(1665-87-8)
• EPA Substance Registry System: 2,5-Cyclohexadien-1-one, 2,4,6-tris(1,1-dimethylethyl)-4-nitro-(1665-87-8)

Safety Data

• Hazardous Substances Data: 1665-87-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,5-Cyclohexadien-1-one, 2,4,6-tris(1,1-dimethylethyl)-4-nitrois used as a reactive intermediate in organic synthesis for the formation of new compounds. Its unique molecular structure allows it to participate in various chemical reactions, making it a valuable component in the creation of diverse chemical entities.
Used in Research Chemistry:
As a research chemical, 2,5-Cyclohexadien-1-one, 2,4,6-tris(1,1-dimethylethyl)-4-nitrois employed in the study of organic chemistry. It aids in understanding the properties and reactivity of similar compounds, contributing to the advancement of chemical knowledge and the discovery of new reaction mechanisms.
Used in Pharmaceutical Synthesis:
2,5-Cyclohexadien-1-one, 2,4,6-tris(1,1-dimethylethyl)-4-nitrois used as a building block in the synthesis of various pharmaceuticals. Its incorporation into the molecular structures of drugs allows for the development of new therapeutic agents with potential applications in the treatment of various diseases and conditions.
Used in Agrochemical Synthesis:
In the agrochemical industry, 2,5-Cyclohexadien-1-one, 2,4,6-tris(1,1-dimethylethyl)-4-nitrois utilized as a key component in the synthesis of agrochemicals. Its role in the development of new pesticides, herbicides, and other agricultural chemicals is crucial for enhancing crop protection and productivity.

Upstream product

• 732-26-3 2,4,6-tri-tert-butylphenoxol 
• 3315-32-0 2,4,6-tri-tert-butylphenoxyl 
• 71-43-2 benzene 

Downstream Products

• 3383-21-9 3,5-di-tert-butyl-o-benzoquinone 
• 4971-61-3 2,4,6-tri-tert-butyl-4-hydroxy-2,5-cyclohexadienone 
• 732-26-3 2,4,6-tri-tert-butylphenoxol 
• 100699-37-4 2,4-di-t-butyl-4,6-dimethoxycyclohexa-2,5-dienone 
• 95872-23-4 2,4,6-tri-t-butyl-4-(4'-methylphenoxy)cyclohexa-2,5-dienone 
• 1020-31-1 3,5-Di-tert-butylcatechol 
• 92892-09-6 2,6-dimethyl-4-nitromethyl-phenol 
• 719-22-2 2,6-Di-tert-butyl-1,4-benzoquinone 
• 70702-91-9 2,4,6-tri-tert-butyl-6-hydroxy-cyclohexa-2,4-dienone 
• 1206714-46-6 1,3,5-tri-tert-butyl-4-oxocyclohexa-2,5-dienyl nitrite 
• 1206714-49-9 1,3,5-tri-tert-butyl-6-oxocyclohexa-2,4-dienyl nitrite 
• 115-11-7 isobutene 

Relevant articles and documents

The slow rearrangement of a sterically hindered nitro-cyclohexadienone and the absence of phenol oxidation by nitrogen monoxide

The exposure of 2,4,6-tri-tert-butylphenol (1) in solution to NO 2 results in the rapid formation of 2,4,6-tri-tert-butyl-4nitro-2,5- cyclohexadienone (2), which then undergoes a slow (ca. 3 d) rearrangement in the absence of air. The mechanism, that describes this rearrangement is understood for the first time and involves the initial isomerization of 2 to form a (-ONO)-substituted cyclohexadieneone (6). The nitrite moiety undergoes bond homolysis releasing NO. while forming an oxyl radical intermediate. An lntermolecular, concerted hydrogen abstraction, which proceeds between 6 and this oxyl radical, results in the simultaneous formation of all stable products, some of which have not been previously observed, Furthermore, when 1 is exposed, to NO. under anaerobic conditions, no reaction is observed. Wiley-VCH Verlag GmbH & Co. KGaA.

New insights into the reactivity of nitrogen dioxide with substituted phenols: A solvent effect

Various alkyl-substituted phenols react readily with nitrogen dioxide (.NO2) in different solvents at room temperature. In all cases nitration is the major reaction and leads to the formation of mono- and dinitrophenols and 4-nitrocyclohexa-2,5-dienones from 2,4,6-tri-substituted phenols. Oxidation, dimerisation and, in one case, nitrosation are also observed. The reaction pathway followed changes according to the solvent and to the nature and the number of substituents on the phenolic ring. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

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.

Reactions of 2-t-Butyl-4,6-dimethylphenol, 2,4-Di-t-butyl-6-methylphenol and 2,4,6-Tri-t-butylphenol with Nitrogen Dioxide

Reaction of 2-t-butyl-4,6-dimethylphenol (10) with nitrogen dioxide in benzene gives the C4-epimeric 4,5,6-trinitrocyclohex-2-enones (13) and (14).In contrast, similar reaction of 2,4-di-t-butyl-6-methylphenol (11) gives substituted cyclohex-3-enones, 2,5,6-trinitro ketones (20)-(23), 2-hydroxy-5,6-dinitro ketones (27) and (28) and the 6-hydroxy-2,5-dinitro ketone (29).Reaction of 2,4,6-tri-t-butylphenol (12) with nitrogen dioxide gives initially the 4-nitro dienone (35), but de-t-butylated products (36) and (37) are formed in long-term reactions.X-ray crystal structures are reported for compounds (13), (14), (21), (22), (23), (27), (28)and (29).