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Usage

Uses

Used in Pharmaceutical Industry:
2,5-Cyclohexadien-1-one,4-fluoro-4-nitro-(9CI) is used as a chemical intermediate for the synthesis of pharmaceutical compounds. Its unique structure with nitro and fluoro groups may contribute to the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical industry, 2,5-Cyclohexadien-1-one,4-fluoro-4-nitro-(9CI) is used as a building block for the creation of novel agrochemicals. Its chemical properties can be harnessed to develop pesticides or herbicides with improved efficacy and selectivity.
Used in Materials Chemistry:
2,5-Cyclohexadien-1-one,4-fluoro-4-nitro-(9CI) is utilized in materials chemistry for the development of new materials with specific properties. Its reactivity and structural features can be exploited to create materials with tailored characteristics for various applications, such as polymers, coatings, or adhesives.

Upstream product

• 459-60-9 1-fluoro-4-methoxybenzene 
• 405-51-6 4-fluorophenyl acetate 
• 371-41-5 4-Fluorophenol 

Downstream Products

• 394-33-2 2-nitro-4-fluorophenol 
• 364-32-9 4-fluoro-2,6-dinitrophenol 

Relevant academic research and scientific papers

The mechanism of the nitration of donor-activated benzenes with nitric and nitrous acid as studied by 15N CIDNP

15N CIDNP effects observed during nitration of phenolic compounds with nitric and nitrous acid are comparable showing that nitrous acid is not only a catalyst during nitration with nitric acid but also a reactive intermediate. The 15N CIDNP effects are generated in radical pairs formed during encounters of NO2 and arene radical cations or aroxyl radicals. The mechanism given is valid for arenes more reactive than toluene.

Formation of 4-Halo-4-nitrocyclohexa-2,5-dienones on Nitration of p-Halophenols and p-Halophenyl Acetates.

Nitration of p-chloro-, p-fluoro-, and p-bromo-phenol or the corresponding p-halophenyl acetates at -40 deg C and below gives the 4-halo-4-nitrocyclohexa-2,5-dienones in addition to the 4-halo-2-nitrophenols.The dienones isomerize to the nitrophenols at temperatures between -40 deg C and 0 deg C.Nitration of 4-chloro-2-methylphenol or its acetate gives both 4-chloro-2-methyl-4-nitrocyclohexa-2,5-dienone and 4-chloro-6-methyl-6-nitrocyclohexa-2,4-dienone. 4-Chloro-3-methylphenol and its acetate give 4-chloro-3-methyl-4-nitrocyclohexa-2,5-dienone.

ipso Nitration in p-halophenyl ethers

Addition of nitronium ion ipso to halogen occurs on nitration of the p-haloanisoles in acetic anhydride at -60 deg C.In the cases of p-fluoro- and p-chloro-anisole, addition of the nitronium ion is reversible and only small amounts of ipso products are obtained.With p-bromoanisole nitrodebromination occurs.When p-halophenyl ethers containing a trapping substituent, e.g., 2-(4-chlorophenoxy)-2-methylpropanoic acid, are used as substrates, substantial amounts of the spiro diene with nitro ipso to halogen, e.g., 3,3-dimethyl-8-chloro-8-nitro-1,4-dioxaspirodeca-6,9-dien-2-one, can be isolated.The results demonstrate that extensive ipso attack at the halogen-substituted position is general in the nitration of p-halophenyl ethers.Key words: ipso nitration, ether, diene, p-haloanisole.