| Description | 2-Methyl-5-nitroaniline, also known as 5-nitro-o-toluidine, is an intermediate compound in the synthesis of a wide range of azo dyes and is an in vivo metabolic product of 2,4-dinitrotoluene. |
Chemical Properties| 5-Nitro-o-toluidine is a yellow, crystallinesolid. |
| Uses | 2-Methyl-5-nitroaniline may be employed as analytical standard for the surfactant mediated transformations (?254nm) of 2,4-dinitrotoluene. |
Uses| 5-Nitro-o-toluidine is used in the synthesis of numerous dyes. |
| Preparation | 2-Methyl-5-nitrobenzenamine?in concentrated sulfuric acid nitration. |
Preparation| o-Toluidine(500 mg, 4.19 mmol) was added with vigorous stirring to a balloon with concentrated sulfuric acid (3.9 ml, 71.4 mmol). The temperature of the reaction is 10 ℃ (salt/ice, cold bath). After that, an acid mixture (0.9 mlHNO3 and 0.9 ml H2SO4) was added to the solution for 2 h. The mixture was placed on ice and basified with NaOH. Finally, 2-methyl-5-nitroaniline was collected by filtration and washed with water. |
| Definition | ChEBI: A C-nitro compound in which the nitro compound is meta to the amino group and para to the methyl group of o-toluidine. |
Air & Water Reactions| Insoluble in water. 2-Methyl-5-nitroaniline is sensitive to moisture, light, or prolonged exposure to air. |
| Reactivity Profile | 2-Methyl-5-nitroaniline is incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides and chloroformates. |
Fire Hazard| Flash point data for 2-Methyl-5-nitroaniline are not available; however, 2-Methyl-5-nitroaniline is probably combustible. |
| Toxicology | Genetic toxicity studies for 2-methyl-5-nitroaniline indicate generally positive results in reverse-mutation assays in Salmonella typhimurium and Escherichia coli, and in Syrian hamster embryo (SHE) cell transformation assays; the compound is weaker in potency than other 2,4-dinitrotoluene metabolites. |
Safety Profile| Confirmed carcinogenwith experimental carcinogenic data.Moderately toxic by ingestion. Mutation datareported. Decomposes exothermically whenheated to 150℃. When heated todecomposition it emits toxic fumes of NOx.See also NITRO COMPOUNDS OFAROMATIC HYDROCARBONS. |
| Carcinogenicity | Thereare no data available for evaluating carcinogenic risk tohumans. When 5-nitro-o-toluidine was administered in adietary feeding study to F344 rats (50 or 100 ppm) andB6C3F1 mice (1200 or 2300 ppm) of both sexes, hepatocellularcarcinomas were produced in mice but not in rats. |
Shipping| UN2660 Nitrotoluidines (mono), Hazard Class:6.1; Labels: 6.1-Poisonous materials. |
| Purification Methods | Acetylate the aniline, and the acetyl derivative is crystallised to constant melting point; then hydrolyse it with 70% H2SO4 and the free base is regenerated by treatment with NH3 [Bevan et al. J Chem Soc 4284 1956]. [Beilstein 12 H 844. 12 IV 1807.] |
Incompatibilities| Incompatible with oxidizers (chlorates,nitrates, peroxides, permanganates, perchlorates, chlorine,bromine, fluorine, etc.); contact may cause fires or explosions.Keep away from alkaline materials, strong bases,strong acids, oxoacids, epoxides, acid chlorides; acid anhydrides;chloroformates. |
| Waste Disposal | Consult with environmentalregulatory agencies for guidance on acceptable disposalpractices. Generators of waste containing this contaminant(≥100 kg/mo) must conform with EPA regulations governingstorage, transportation, treatment, and waste disposal. |
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