3463-36-3

Basic information

• Product Name: 1,2,4,5-tetramethyl-3-nitrobenzene
• Synonyms: 1,2,4,5-Tetramethyl-3-nitrobenzene; benzene, 1,2,4,5-tetramethyl-3-nitro-
• CAS NO: 3463-36-3
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.2157
• Mol File: 3463-36-3.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 283.6°C at 760 mmHg
• Flash Point: 122.5°C
• Density: 1.077g/cm³
• Vapor Pressure: 0.00536mmHg at 25°C
• Refractive Index: 1.538
• CAS DataBase Reference: 1,2,4,5-tetramethyl-3-nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4,5-tetramethyl-3-nitrobenzene(3463-36-3)
• EPA Substance Registry System: 1,2,4,5-tetramethyl-3-nitrobenzene(3463-36-3)

Safety Data

• Hazardous Substances Data: 3463-36-3(Hazardous Substances Data)

Usage

Structure

A derivative of benzene with four methyl group substituents and a nitro group at the 3-position

Physical state

Yellow crystalline solid

Uses

a. Precursor in the synthesis of various organic compounds and pharmaceuticals
b. Manufacturing of dyes, perfumes, and insecticides
c. Potential use as a corrosion inhibitor

Toxicological properties

Studied for its potential toxicological effects

Hazards

a. Toxic and hazardous substance
b. Can cause irritation to the skin, eyes, and respiratory system
c. Exposure to 1,2,4,5-tetramethyl-3-nitrobenzene can be harmful

Upstream product

• 95-93-2 1,2,4,5-tetramethylbenzene 
• 67-66-3 chloroform 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 509-14-8 tetranitromethane 
• 13171-61-4 2,3,5,6-tetramethyl-4-amino-1-nitrobenzene 
• 38899-21-7 2,3,5,6-tetramethylnitrosobenzene 

Downstream Products

• 134592-01-1 (E)-9-(4-amino-2,3,5,6-tetramethylstyryl)acridine 
• 134592-00-0 (Z)-9-(4-amino-2,3,5,6-tetramethylstyryl)acridine 
• 134592-04-4 (E)-9-(2,3,5,6-tetramethyl-4-nitrostyryl)acridine 
• 134592-02-2 2,3,5,6-tetramethyl-4-nitrobenzaldehyde 
• 46010-72-4 aminodurenol 
• 2217-46-1 2,3,5,6-tetramethylaniline 
• 5465-13-4 dinitrodurene 
• 58149-28-3 2,3,5,6-tetramethylphenylisocyanate 
• 30075-67-3 2,3,5,6-tetramethyl-4-nitrobenzyl chloride 
• 527-35-5 2,3,5,6-tetramethylphenol 

Relevant articles and documents

HNO3/HFIP: A Nitrating System for Arenes with Direct Observation of π-Complex Intermediates

This report describes an efficient nitrating system for the nitration of arenes at room temperature by using an equivalent of nitric acid in HFIP (1,1,1,3,3,3-hexafluoroisopropanol). The π-complex intermediate of an arene with a nitronium ion stabilized by HFIP can be directly observed by UV-vis spectra and is supported by theoretical calculations.

Photochemical nitration by tetranitromethane. Part XXXIII. Adduct formation in the photochemical reactions of 1,2,4,5- and 1,2,3,5-tetramethylbenzene

The photolysis of the charge-transfer complex of tetranitromethane and 1,2,4,5-tetramethylbenzene in dichloromethane or acetonitrile gives the epimeric 1,3,4,6-tetramethyl-3-nitro-6-trinitromethylcyclohexa-1,4-dienes 8 and 9, in addition to products of nuclear nitration 12 and side-chain modification 10, 11, and 13-18. Similar reactions of 1,2,3,5-tetramethylbenzene gave trans-1,3,5,6-tetramethyl-6-nitro-3-trinitromethylcyclohexa-1,4-diene 30 and two isomeric 'double' adducts 31 and 32, in addition to products of nuclear nitration 27 and side-chain modification 26, 28 and 29. The eliminative rearrangements of adducts 8 and 30 to give re-aromatized products in acetonitrile or [2H3] acetonitrile and in [2H] chloroform are reported. The photolysis of the charge-transfer complexes of tetranitromethane with either 1,2,4,5-tetramethylbenzene or 1,2,3,5-tetramethylbenzene in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFP) gives a marked increase in the yields of ring-nitration products 12 or 27, respectively, reactions presumed to proceed via a nitrosation-oxidation sequence. Reaction of 1,2,4,5-tetramethylbenzene with excess nitrogen dioxide in HFP also results in extensive ring nitration to give 12 and 2,3,5,6-tetramethyl-1,4-dinitrobenzene (25); the latter compound is seen as arising via the 2,3,5,6-tetramethyl-1,4-dinitrosobenzene (34). Similar reaction of 1,2,3,5-tetramethylbenzene gives ring-nitration product 27 as the major product. X-Ray crystal structures are reported for 2,4,6-trimethyl-1-(2′,2′,2′-trinitroethyl)benzene (26) and trans-1,3,5,6-tetramethyl-6-nitro-3-trinitromethyl-cyclohexa-1,4-diene (30). Acta Chemica Scandinavica 1996.

Direct Nitrosation of Aromatic Hydrocarbons and Ethers with the Electrophilic Nitrosonium Cation

Various polymethylbenzenes and anisoles are selectively nitrosated with the electrophilic nitrosonium salt NO(1+)BF4(1-) in good conversions and yields under mild conditions in which the conventional procedure (based on nitrile neutralization with strong acid) is ineffective.The reactivity patterns in acetonitrile deduced from the various time/conversions in Tables 2 and 3 indicate that aromatic nitrosation is distinctly different from those previously established for electrophilic aromatic nitration.The contrasting behavior of NO(1+) in aromatic nitrosation is ascribed to a rate-limiting deprotonation of the reversibly formed Wheland intermediate, which in the case of aromatic nitration with NO2(1+) occurs with no deuterium kinetic isotope effect.Aromatic nitroso derivatives (unlike the nitro counterpart) are excellent electron donors that are subject to a reversible one-electron oxidation at positive potentials significantly less than that of the parent polymethylbenzene or anisole.As a result, the series of nitrosobenzenes are also much better Broensted bases than the corresponding nitro derivatives, and this marked distinction, therefore, accounts for the large differentiation in the deprotonation rates of their respective conjugate acids (i.e.Wheland intermediates).