2,3-DIMETHYL-6-NITROANILINE Chemical Properties

Melting point:

117-120 °C(lit.)

Boiling point:

314.38°C (rough estimate)

Density 

1.220±0.06 g/cm3 (20 ºC 760 Torr)

refractive index 

1.6273 (estimate)

storage temp. 

2-8°C, protect from light

form 

Crystalline Powder

pka

-0.16±0.25(Predicted)

color 

Dark yellow to orange-brown

CAS DataBase Reference

59146-96-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

RIDADR 

2811

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214200

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

2,3-DIMETHYL-6-NITROANILINE Usage And Synthesis

Chemical Properties

dark yellow to orange-brown crystalline powder

Uses

2,3-Dimethyl-6-nitroaniline is an aromatic compound used in the study of C-H pi interactions and pi-pi stacking. 

Application

2,3-Dimethyl-6-nitroaniline exhibits solubility in water, ethanol, and acetone, making it a versatile reagent for diverse scientific research applications.

Synthesis

General procedure for the synthesis of 2,3-dimethyl-6-nitroaniline and 2,3-dimethyl-4-nitroaniline from the compounds (CAS:114166-32-4) and N-(2,3-dimethyl-6-nitrophenyl)acetamide: To a solution of N-(2,3-dimethyl-6-nitrophenyl)acetamide (16.0 g, 1.0 equiv.) was added a 60% H2SO4 solution (150 mL). The reaction mixture was heated to reflux temperature, maintained for 1 hour and then cooled to room temperature. The solution was diluted with ice water (100 mL) and neutralized with 2N NaOH solution. The reaction mixture was extracted with EtOAc (3 x 50 mL). The organic phases were combined, washed sequentially with saturated NaHCO3 solution (2 × 50 mL) and saturated NaCl solution (2 × 50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (10% CH2Cl2/hexane) to afford 2,3-dimethyl-6-nitroaniline (5.5 g, 43%) and 2,3-dimethyl-4-nitroaniline (1.5 g, 12%). 1H NMR data for 2,3-dimethyl-6-nitroaniline (5.5 g, 43%): δ 2.05 (s, 3H), 2.20 (s, 3H), 6.15 (br s, 2H), 6.45 (d, J=8.7 Hz, 1H), 7.63 (d, J=9.0 Hz, 1H) in CDCl3; δ 2.10 (s 3H), 2.30 (s, 3H), 6.50 (d, J=8.7Hz, 1H), 7.15 (br s, 2H), 7.75 (d, J=9.0Hz, 1H). 1H NMR data for 2,3-dimethyl-4-nitroaniline: δ 2.10 (s, 3H), 2.45 (s, 3H), 4.05 (br s, 2H), 6.45 (d, J=9.0 Hz, 1H), 7.65 (d, J=8.7 Hz, 1H) in CDCl3; δ 2.00 (s, 3H), 2.35 (s 3H), 6.12 (br s, 2H), 6.53 (d, J=9.0 Hz, 1H), 7.63 (d, J=9.0 Hz, 1H).

References

[1] Patent: US6353006, 2002, B1. Location in patent: Page column 28-29

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