2-Methyl-6-nitroaniline Chemical Properties

Melting point:

93-96 °C (lit.)

Boiling point:

124 °C / 1mmHg

Density 

1.19 g/cm3

refractive index 

1.6276 (estimate)

Flash point:

110 °C

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

<1mg/l

pka

-0.44±0.25(Predicted)

form 

Crystalline Powder

color 

Brownish

Water Solubility 

<0.1 g/100 mL at 23 ºC

BRN 

1868029

CAS DataBase Reference

570-24-1(CAS DataBase Reference)

NIST Chemistry Reference

2-Methyl-6-nitroaniline(570-24-1)

EPA Substance Registry System

2-Methyl-6-nitroaniline (570-24-1)

Safety Information

Hazard Codes 

T,N,Xi

Risk Statements 

23/24/25-33-51/53

Safety Statements 

28-36/37-45-61-28A

RIDADR 

UN 2660 6.1/PG 3

WGK Germany 

3

F 

10

Hazard Note 

Toxic

HazardClass 

6.1

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

29214300

MSDS

• Language:English Provider:2-Amino-3-nitrotoluene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

2-Methyl-6-nitroaniline Usage And Synthesis

Uses

2-Methyl-6-nitroaniline is a compound useful in organic synthesis. Dyes and metabolites, Environmental Testing.

Chemical Properties

Redish-Brown Solid

Uses

2-Methyl-6-nitroaniline (cas# 570-24-1) is a compound useful in organic synthesis. Dyes and metabolites, Environmental Testing

General Description

Orange-yellow prisms or brown granular powder.

Air & Water Reactions

2-Methyl-6-nitroaniline is sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

2-Methyl-6-nitroaniline is incompatible with acids, acid chlorides, acid anhydrides, chloroformates, and strong oxidizers.

Fire Hazard

Flash point data for 2-Methyl-6-nitroaniline are not available, but 2-Methyl-6-nitroaniline is probably combustible.

Synthesis

The general procedure for the synthesis of 2-methyl-6-nitroaniline from 2-methylacetanilide was carried out as follows: the modified Howard method [27] was used. Toluidine (1a or 1b; 53.5 mL, 0.5 mol) was slowly added to acetic anhydride (325 mL) in batches while maintaining constant stirring. The reaction solution was cooled to 12-13 °C in an ice-salt bath. Subsequently, 70% nitric acid (63 mL) was slowly added dropwise to the reaction mixture at a rate that maintained the temperature at 10-12 °C with constant stirring. The dropwise addition process took 2.5 h to complete, after which the solution was poured into 1.5 L of ice water. The resulting acetamide (3a, or a mixture of 3b and 3c) precipitate (as a cream-colored solid) was collected on a Brinell's funnel, washed with four 250 mL portions of ice water, and partially dried by suction. The wetted acetamide (3a, or a mixture of 3b and 3c) was mixed with 70% sulfuric acid (100 mL) and stirred at reflux for 3 hours. The acetamide 3b was separated from the reaction mixture by steam distillation to give the hydrolysis product of 2-methyl-6-nitroaniline (4b). After the distiller was cooled, the isolated bright orange needle-like crystals 4b were collected on a Brinell funnel and dried in a vacuum desiccator. If acetamide 3a was hydrolyzed, the warm reaction mixture was diluted with 350 mL of water and alkalized with 10% aqueous sodium hydroxide. After cooling to room temperature, 4-methyl-2-nitroaniline (4a) precipitated as a brown powder, which was separated by vacuum filtration, washed with three parts of 200 mL of water, and dried in a vacuum desiccator. The yields of compounds 4a and 4b were 53.6% (40.73 g) and 52.3% (39.78 g), respectively.

References

[1] Bulletin des Societes Chimiques Belges, 1969, vol. 78, p. 571 - 582
[2] Chemistry Letters, 1989, p. 1849 - 1852
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 13, p. 6047 - 6060
[4] Polyhedron, 2016, vol. 105, p. 137 - 149

2-Methyl-6-nitroaniline(570-24-1)Related Product Information

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