85653-54-9

Basic information

• Product Name: 4-Ethoxy-3-Nitrotoluene
• Synonyms: 4-Ethoxy-3-Nitrotoluene;2-nitro-4-methylphenetole;1-Ethoxy-4-methyl-2-nitrobenzene
• CAS NO: 85653-54-9
• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 181.18854
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 85653-54-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Ethoxy-3-Nitrotoluene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Ethoxy-3-Nitrotoluene(85653-54-9)
• EPA Substance Registry System: 4-Ethoxy-3-Nitrotoluene(85653-54-9)

Safety Data

• Hazardous Substances Data: 85653-54-9(Hazardous Substances Data)

Usage

General Description

4-Ethoxy-3-Nitrotoluene is an organic chemical compound with the molecular formula C9H11NO3. It is a nitro derivative of toluene with an ethoxy group attached to the benzene ring. 4-Ethoxy-3-Nitrotoluene is primarily used as an intermediate in the synthesis of various pharmaceuticals, agrochemicals, and dyes. It is known for its pale yellow to orange crystalline appearance, and it is considered to be a hazardous substance due to its potential for causing skin and eye irritation. The chemical is also flammable and should be handled with care when used in industrial processes.

Upstream product

• 78-10-4 tetraethoxy orthosilicate 
• 1225036-72-5 potassium 4-methyl-2-nitrobenzoate 
• 119-33-5 4-methyl-2-nitrophenol 
• 75-03-6 ethyl iodide 
• 74-96-4 ethyl bromide 
• 622-60-6 1-ethoxy-4-methylbenzene 
• 64-67-5 diethyl sulfate 

Downstream Products

• 23385-48-0 5-Methyl-2-aethoxy-thiophenol 
• 6331-70-0 2-ethoxy-5-methylaniline 

Relevant articles and documents

Copper-mediated ortho-nitration of (hetero)arenecarboxylates

Various (hetero)arenecarboxylic acids were converted to the corresponding Daugulis amides and nitrated selectively in the ortho-position in the presence of [CuNO3(PPh3)2] and AgNO2 at 50 °C. A microwave-assisted saponification allows regenerating the carboxylate group within minutes, which may then be removed tracelessly by protodecarboxylation, or substituted by aryl- or alkoxy-groups via decarboxylative cross-coupling.

Nighttime tropospheric chemistry: Kinetics and product studies in the reaction of 4-Alkyl- and 4-Alkoxytoluenes with NO3 in gas phase

Alkylbenzenes are important constituents of gasoline and industrial solvents and contribute to the formation of tropospheric ozone. The removal of these compounds from the troposphere is due to reaction with OH during the day and with NO3 during the night. Five para-substituted toluenes are reacted with the nitrate radical in gas phase. Samples to be used for product analysis were preconcentrated and analyzed by GC-MSD analysis with the use of a reference curve. The yields of methanol, ethanol, and formaldehyde were determined by FTIR analysis of the reaction mixture in the chamber. Carbonyl compounds, benzyl alcohols, and nitroderivatives were formed. In the case of the alkoxytoluenes, products were also an alkanol, benzyl alcohols, and nitrophenols. Indirect rate constants measurements were performed by comparing by FTIR measurements the decay of the aromatic compound under investigation to that of a reference compound, with a known rate constant for the reaction with NO3 added to the gas mixture. Wall loss constants were evaluated by FTIR. A Hammett correlation with ρ = - 4.3 ± 0.6; r2-= 0.87 was obtained. This and the kinetic isotope effect of 1.5-1.8 suggest a reaction mechanism occurring via an addition-elimination pathway.