4,6-DIMETHYL-2-NITROANILINE Chemical Properties

Melting point:

64-68 °C(lit.)

Boiling point:

319.1±37.0 °C(Predicted)

Density 

1.220±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Store in freezer, under -20°C

pka

0.27±0.25(Predicted)

Appearance

Yellow to orange Solid

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-37/39

RIDADR 

UN2811

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214990

MSDS

• Language:English Provider:SigmaAldrich

4,6-DIMETHYL-2-NITROANILINE Usage And Synthesis

Uses

2,4-Dimethyl-6-nitroaniline is used as a reagent in the synthetic preparation of 1,2-bis-substituted benzimidazoles as nonnucleoside HIV-1 reverse transcriptase inhibitors.

Synthesis

General procedure for the synthesis of 2-nitro-4,6-dimethylaniline from 2,4-dimethylaniline: 2,4-dimethylaniline (8.0 g, 66.0 mmol) was dissolved in acetic anhydride (50 mL) and concentrated nitric acid (5 mL) was added slowly and dropwise at 0 °C. The reaction mixture was stirred at 0 °C for 30 min and then diluted with ice water (200 mL). Subsequently, concentrated hydrochloric acid (10 mL) was added dropwise to the mixture and the resulting mixture was stirred under reflux conditions for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the solvent was removed by distillation under reduced pressure. The residue was diluted with aqueous ammonium hydroxide and the resulting orange solid was filtered and dried to give 2-nitro-4,6-dimethylaniline (10.6 g, 97% yield).

References

[1] Patent: WO2009/25478, 2009, A1. Location in patent: Page/Page column 33; 52-53
[2] Patent: US2010/197673, 2010, A1. Location in patent: Page/Page column 15
[3] Patent: KR101511771, 2015, B1. Location in patent: Paragraph 0406; 0407
[4] Tetrahedron Asymmetry, 2003, vol. 14, # 10, p. 1267 - 1273
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 21, p. 8743 - 8749

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