3-Methyl-2-nitroaniline Chemical Properties

Melting point:

107-108 °C

Boiling point:

288.6±20.0 °C(Predicted)

Density 

1.269±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

crystalline powder

pka

-0.11±0.10(Predicted)

color 

Orange

InChI

InChI=1S/C7H8N2O2/c1-5-3-2-4-6(8)7(5)9(10)11/h2-4H,8H2,1H3

InChIKey

VDCZKCIEXGXCDJ-UHFFFAOYSA-N

SMILES

C1(N)=CC=CC(C)=C1[N+]([O-])=O

Safety Information

HS Code 

2921420090

3-Methyl-2-nitroaniline Usage And Synthesis

Uses

3-Methyl-2-nitroaniline is used in the purification of 2-Methoxy-5-trifluoromethoxybenzaldehyde. It also an important component in preparing benzimidazoles. It is used in palladium-catalyzed synthesis of quinoxline deriitives.

Synthesis

General procedure for the synthesis of 3-methyl-2-nitroaniline from 3-methyl-2-nitrobenzamide: NaOH (2.220 g, 55.5 mmol) was dissolved in water (12 mL) at 0°C, followed by the addition of Br2 (0.322 mL, 6.26 mmol). Next, 3-methyl-2-nitrobenzamide (1 g, 5.55 mmol) was added all at once and the mixture was slowly heated in a water bath to 50-55°C (internal temperature), at which point oil droplets were observed to separate. The temperature was continued to be gradually increased to 70°C and maintained at this temperature for 1 hour. Subsequently, a solution of NaOH (0.7 g) dissolved in water (4 mL) was added and the temperature was slowly raised to 80°C and held for another 1 hour. After completion of the reaction, it was cooled to room temperature and extracted with EtOAc (3x50mL). The organic layers were combined, dried and concentrated to give 0.7 g (90% yield) of the target compound 3-methyl-2-nitroaniline.LC-MS analysis showed m/z of 153.1 (M + H)+ and retention time of 1.65 min.

References

[1] Patent: WO2015/92713, 2015, A1. Location in patent: Page/Page column 73; 74
[2] Patent: WO2016/203400, 2016, A1. Location in patent: Page/Page column 49
[3] Patent: WO2016/203401, 2016, A1. Location in patent: Page/Page column 60; 61
[4] Patent: WO2016/202253, 2016, A1. Location in patent: Page/Page column 126; 127
[5] Patent: WO2018/104766, 2018, A1. Location in patent: Page/Page column 60-61

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