943-15-7

Usage

Uses

Used in Chemical Synthesis:
2-NITRO-4-CYMENE is used as a chemical intermediate for the synthesis of 5-isopropyl-8-methylquinoline, a compound with potential applications in various chemical processes and industries.
Used in Electrochemistry:
In the electrochemistry field, 2-NITRO-4-CYMENE is utilized as a mediator solvent in perchlorate ion-selective electrodes. This application takes advantage of its properties within a poly(vinyl chloride) matrix membrane on a conductive silver-epoxy composite, enhancing the electrode's selectivity and performance in detecting perchlorate ions.
Used in Dye Industry:
Reduction products of 2-NITRO-4-CYMENE are significant as dye intermediates, playing a crucial role in the production of various dyes and pigments. This makes it an essential component in the dye industry, contributing to the development of a wide range of colorants for different applications.

InChI:InChI=1/C10H13NO2/c1-7(2)9-5-4-8(3)10(6-9)11(12)13/h4-7H,1-3H3

Upstream product

• 99-87-6 4-methylisopropylbenzene 
• 88-72-2 1-methyl-2-nitrobenzene 
• 67-63-0 isopropyl alcohol 
• 108-20-3 di-isopropyl ether 
• 56-23-5 tetrachloromethane 
• 7664-93-9 sulfuric acid 
• 52834-93-2 4-methyl-1-(1'-methylethyl)-t-4-nitrocyclohexa-2,5-dien-r-1-yl acetate 

Downstream Products

• 61263-70-5 bis-(5-isopropyl-2-methyl-phenyl)-diazene-N-oxide 
• 2051-53-8 5-isopropyl-2-methylphenylamine 
• 99068-90-3 5-isopropyl-2-methyl-1,3-dinitro-benzene 
• 1128-28-5 4-aminothymol 
• 858514-10-0 N-(5-isopropyl-2-methyl-phenyl)-hydroxylamine 
• 128196-18-9 3-chloro-5-isopropyl-2-methyl-aniline 
• 128175-69-9 1-chloro-5-isopropyl-2-methyl-3-nitro-benzene 
• 51556-93-5 trans-2,2'-Azo-p-cymene 
• 592478-90-5 1-(2,2-dimethoxy-ethyl)-4-isopropyl-2-nitro-benzene 
• 119056-41-6 5,5'-diisopropyl-2,2'-dimethyl-4,4'-benzylidene-di-phenol 
• 860405-03-4 bis-(4-amino-2-isopropyl-5-methyl-phenyl)-phenyl-methane 
• 860405-06-7 N-(4-amino-2-isopropyl-5-methyl-benzhydryl)-5-isopropyl-2-methyl-aniline 
• 861618-69-1 2-(carboxymethyl-amino)-4-(α-hydroxy-isopropyl)-benzoic acid 
• 35480-95-6 4-isopropyl-2-nitro-benzoic acid 

Relevant academic research and scientific papers

Reactions of 4-Methyl-1-(1'-methylethyl)-4-nitrocyclohexa-2,5-dien-1-yl Acetates with Nitrogen Dioxide: Towards a Mechanism for the Formation of Polynitro Cyclohexenyl Esters on Reaction of p-Cymene with Nitrogen Dioxide in Acetic Anhydride

The acetoxy nitro diene (21), the C3-epimeric 3,4,6-trinitro-5-nitratocyclohexenes (24) and (25) , the 3,6-dinitro-5-nitratocyclohexa-1,3-diene (29), and the 3,6-dinitro-5-acetoxycyclohexa-1,3-diene (32) are identified as probable intermediates in the formation of polynitro cyclohexenyl esters (4)-(13) on reaction of p-cymene with nitrogen dioxide in acetic anhydride; probable reaction pathways are discussed.The X-ray crystal analysis of 4-methyl-1-(1'-methylethyl)-t-5-nitrato-r-3,t-4,c-6-trinitrocyclohexene (24) is reported.

The Nitration of p-Cymene with Nitrogen Dioxide in Acetic Anhydride

Reaction of p-cymene (1) with nitrogen dioxide in acetic anhydride gives polynitro nitrates (4)-(10), polynitro acetates (11)-(13), and nitro aromatic compounds (14)-(17).X-Ray crystal analyses are reported for compounds (5)-(9), (11) and (12).

THE NITRATION OF p-CYMENE WITH NITROGEN DIOXIDE IN ACETIC ANHYDRIDE: THE ISOLATION AND X-RAY STRUCTURE DETERMINATION OF 6-METHYL-3-(METHYLETHYL)-t-5-NITRATO-1,r-3,c-4,t-6-TETRANITROCYCLOHEXENE

Reaction of p-cymene (1a) with nitrogen dioxide in acetic anhydride gives 2-nitro-p-cymene (1b), p-nitrotoluene (2), and the tetranitronitratocyclohexene (3) as the major products; the X-ray crystal structure of (3) is reported.

Electrophilic aromatic substitution. Part 24. The nitration of isopropylbenzene, 2- and 4-isopropyltoluene, 1-chloro-4-isopropylbenzene, 4-isopropylanisole, and 2-bromotoluene: Nitrodeisopropylation

The kinetics and products of nitration in aqueous sulphuric acid of the title compounds have been studied. 4-Isopropyl-phenol and -anisole are nitrated at or near the encounter rate. In 65-79% H2SO4 2-isopropyltoluene suffers ca. 25% ipso-attack; the only fate of W iPri (ipso-Wheland intermediate) is nitrodeisopropylation. From 4-isopropyltoluene WiPri is also nitrodeisopropylated, but some 1,2-nitro-migration may occur. From the same compound WiMe may be captured by water, rearrange, or give 4-methylacetophenone; a mechanism is proposed for the formation of the last compound. Nitrodeisopropylation occurs without the assistance of water. With 4-isopropylanisole, demethoxylation and nitrodeisopropylation are consequences of the formation of WiPri. The results are consistent with increasing attack at C-4 with increasing acidity, loss of isopropyl without assistance from water, and decomposition of the unobserved intermediate, 4-isopropyl-4-nitrocyclohexa-2,5-dienone, by two processes. One, acid-catalysed process gives 4-nitrophenol and possibly 4-isopropyl-2-nitrophenol. The other, probably radical, process gives 4-isopropyl-2-nitrophenol. In contrast to 4-bromotoluene, 2-bromotoluene is not nitrodebrominated.