2-Methyl-5-nitroaniline Chemical Properties

Melting point:

103-106 °C(lit.)

Boiling point:

294.61°C (rough estimate)

Density 

1.2333 (estimate)

refractive index 

1.6276 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Crystalline Powder

pka

2.34±0.10(Predicted)

color 

Ochre to yellow-orange

Water Solubility 

<0.1 g/100 mL at 19 ºC

BRN 

879021

Exposure limits

ACGIH: TWA 1 mg/m3

Stability:

Stable. Incompatible with strong oxidizing agents, acid chlorides, acid anhydrides, acids, chloroformates.

CAS DataBase Reference

99-55-8(CAS DataBase Reference)

NIST Chemistry Reference

Benzenamine, 2-methyl-5-nitro-(99-55-8)

IARC

3 (Vol. 48) 1990

EPA Substance Registry System

2-Methyl-5-nitroaniline (99-55-8)

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

23/24/25-40-52/53

Safety Statements 

36/37-45-61

RIDADR 

UN 2660 6.1/PG 3

WGK Germany 

3

RTECS 

XU8225000

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214300

Hazardous Substances Data

99-55-8(Hazardous Substances Data)

Toxicity

LD50 orl-rat: 574 mg/kg NCIMR* NIH-71-E-2144,73

MSDS

• Language:English Provider:C.I. 37105
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Methyl-5-nitroaniline Usage And Synthesis

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, crystalline solid.

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 carcinogen with experimental carcinogenic data. Moderately toxic by ingestion. Mutation data reported. Decomposes exothermically when heated to 150℃. When heated to decomposition it emits toxic fumes of NOx. See also NITRO COMPOUNDS OF AROMATIC HYDROCARBONS.

Carcinogenicity

There are no data available for evaluating carcinogenic risk to humans. When 5-nitro-o-toluidine was administered in a dietary feeding study to F344 rats (50 or 100 ppm) and B6C3F1 mice (1200 or 2300 ppm) of both sexes, hepatocellular carcinomas 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 environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.

2-Methyl-5-nitroaniline(99-55-8)Related Product Information

• Betaine
• 2,3-DIAMINOTOLUENE
• Methyl acetate
• Kresoxim-methyl
• DINITROTOLUENE
• ALTRENOGEST
• Methylparaben
• Paraquat dichloride
• 3-Nitrotoluene
• Basic Violet 1
• Methanol
• Acetonitrile
• Toluidine Blue O
• 2-Nitrotoluene
• p-Toluidine
• Glycine
• Methyl acrylate
• 3-Aminobenzotrifluoride