10439-77-7

Basic information

• Product Name: N-METHYL-4-NITRO-O-TOLUIDINE
• Synonyms: 2,N-Dimethyl-4-nitroaniline;N,2-Dimethyl-4-nitrobenzeneamine;N,2-Dimethyl-4-nitroaniline 2-(Methylamino)-5-nitrotoluene;Methyl-(2-methyl-4-nitro-phenyl)-amine;N-Methyl-4-nitro-o-toluidine;2-(METHYLAMINO)-5-NITROTOLUENE;N-METHYL-4-NITRO-O-TOLUIDINE;N,2-DIMETHYL-4-NITROANILINE
• CAS NO: 10439-77-7
• Molecular Formula: C₈H₁₀N₂O₂
• Molecular Weight: 166.18
• Product Categories: Organic Nonlinear Optical Materials;Functional Materials
• Mol File: 10439-77-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 138 °C
• Boiling Point: 310.3 °C at 760 mmHg
• Flash Point: 141.5 °C
• Appearance: /
• Density: 1.212 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: very faint turbidity in hot Methanol
• CAS DataBase Reference: N-METHYL-4-NITRO-O-TOLUIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-METHYL-4-NITRO-O-TOLUIDINE(10439-77-7)
• EPA Substance Registry System: N-METHYL-4-NITRO-O-TOLUIDINE(10439-77-7)

Safety Data

• Hazardous Substances Data: 10439-77-7(Hazardous Substances Data)

Usage

General Description

N-Methyl-4-nitro-o-toluidine is a chemical compound used in several industrial applications. Structurally, it is an aromatic amine composed of a benzene ring with nitro, methyl and amino functional groups attached. Its molecular formula is C8H9N3O2. Its primary use is in dye manufacture where it serves as an intermediate, and it is also used in the production of other chemicals. As with many chemicals, caution is required when handling – it is harmful if inhaled, swallowed, or if it comes into contact with the skin. It is also categorized as hazardous for the environment, particularly aquatic life.

Upstream product

• 333-27-7 methyl trifluoromethanesulfonate 
• 99-52-5 2-methyl-4-nitro-benzenamine 
• 100-39-0 benzyl bromide 
• 616-38-6 carbonic acid dimethyl ester 
• 10596-01-7 N-methyl-N-nitroso-o-toluidine 
• 26198-11-8 N-formyl-2-methyl-4-nitroaniline 
• 7664-93-9 sulfuric acid 
• 156461-85-7 N-methyl-N-nitro-o-toluidine 
• 64-19-7 acetic acid 
• 32417-73-5 N,2-dimethyl-5-nitroformanilide 
• 74-88-4 methyl iodide 
• 90918-52-8 acetic acid-(2,N-dimethyl-4-nitro-anilide) 
• 124-41-4 sodium methylate 
• 6370-27-0 2,N-dimethyl-4-nitroso-aniline 

Downstream Products

• 32417-73-5 N,2-dimethyl-5-nitroformanilide 

Relevant articles and documents

Self-Immolative System for Disclosure of Reactive Electrophilic Alkylating Agents: Understanding the Role of the Reporter Group

The development of stable, efficient chemoselective self-immolative systems, for use in applications such as sensors, requires the optimization of the reactivity and degradation characteristics of the self-immolative unit. In this paper, we describe the effect that the structure of the reporter group has upon the self-immolative efficacy of a prototype system designed for the disclosure of electrophilic alkylating agents. The amine of the reporter group (a nitroaniline unit) was a constituent part of a carbamate that functioned as the self-immolative unit. The number and position of substituents on the nitroaniline unit were found to play a key role in the rate of self-immolative degradation and release of the reporter group. The position of the nitro substituent (meta- vs para-) and the methyl groups in the ortho-position relative to the carbamate exhibited an influence on the rate of elimination and stability of the self-immolative system. The ortho-methyl substituents imparted a twist on the N-C (aromatic) bond leading to increased resonance of the amine nitrogen's lone pair into the carbonyl moiety and a decrease of the leaving character of the carbamate group; concomitantly, this may also make it a less electron-withdrawing group and lead to less acidification of the eliminated β-hydrogen.

N-Methylation of poorly nucleophilic aromatic amines with dimethyl carbonate

Abstract: Dimethyl carbonate (DMC), an environmentally friendly methylation agent, is a substitute for traditional methylation agents such as methyl halides (CH3X, X?=?I, Br, Cl) or dimethyl sulfate. An efficient, convenient, and green method has been developed for N-methylation of poorly nucleophilic aromatic amines with DMC. It was found that the couple PEG400/K2CO3 provides good selectivity for the N-methylation product. Finally, the mechanism for reaction of amines with DMC was investigated, and a plausible multistep mechanism proposed and verified. Graphical Abstract: [Figure not available: see fulltext.]

Organophosphorus Compounds. XX. Approaches to the Synthesis of 2,3-Dihydro-1H-1.2-benzazaphospholes Involving C-C and C-P Ring Closure

Reaction of chloromethylphosphonic dichloride (9) with N-methylaniline gave N,N'-dimethyl-N,N'-diphenylchloromethylphosphonodiamide (10) which upon treatment with aluminium chloride underwent intramolecular Friedel-Crafts alkylation to afford 1-methyl-2-(N'-methyl-N'-phenylamino)-2,3-dihydro-1H-1,2-benzazaphosphole 2-oxide (13a).Similarly, N-methyl-N-phenyl(chloromethyl)phenylphosphinamide (15) was cyclized to give 1-methyl-2-phenyl-2,3-dihydro-1H-1,2-benzazaphosphole 2-oxide (13b). Some unsuccessful approaches to this heterocyclic ring system are also reported.