943-15-7

Basic information

• Product Name: 2-NITRO-4-CYMENE
• Synonyms: 4-Isopropyl-1-methyl-2-nitrobenzene;4-isopropyl-1-methyl-2-nitro-benzene;4-Isopropyl-2-nitrotoluene;Benzene, 1-methyl-4-(1-methylethyl)-2-nitro-;Methyl-4-isopropyl-2-nitro-benzene;2-NITRO-PARA-CYMENE, TECH., 90%;1-METHYL-4-(1-METHYLETHYL)-2-NITROBENZENE;2-Nitro-4-cymene,90%,tech.
• CAS NO: 943-15-7
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.22
• EINECS: 213-397-2
• Product Categories: Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 943-15-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 1°C (estimate)
• Boiling Point: 134 °C / 15mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.07 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.055mmHg at 25°C
• Refractive Index: n20/D 1.528(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 2-NITRO-4-CYMENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NITRO-4-CYMENE(943-15-7)
• EPA Substance Registry System: 2-NITRO-4-CYMENE(943-15-7)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 36/37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 943-15-7(Hazardous Substances Data)

Usage

Uses

2-Nitro-p-cymene was used in the synthesis of 5 -isopropyl-8-methylquinoline. It was used as mediator solvent in perchlorate ion-selective electrode with poly(vinyl chloride) matrix membrane on conductive silver-epoxy composite.

General Description

Reduction products of 2-nitro-p-cymene are significant dye intermediates.

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

Upstream product

• 88-72-2 1-methyl-2-nitrobenzene 
• 67-63-0 isopropyl alcohol 
• 108-20-3 di-isopropyl ether 
• 56-23-5 tetrachloromethane 
• 99-87-6 4-methylisopropylbenzene 
• 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 
• 204850-17-9 2-amino-4-isopropyl-benzoic acid methyl ester 
• 681292-74-0 2-amino-5-iodo-4-isopropyl-benzoic acid methyl ester 
• 681292-73-9 4-isopropyl-2-nitro-benzoic acid methyl ester 
• 774165-27-4 2-amino-4-isopropylbenzoic acid 
• 500303-64-0 ethyl N-[2-(2-aminoethyl)-5-isopropylphenyl]oxalamate hydrochloride 

Relevant articles and documents

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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).

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.