4-ISOPROPYL-2-NITROANILINE Chemical Properties

Melting point:

36-39

Boiling point:

142-144/0.4mm

Density 

1.172±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

0.40±0.10(Predicted)

Appearance

Yellow to orange Solid

Safety Information

Hazard Codes 

T

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

Hazard Note 

Toxic

HS Code 

2921420090

4-ISOPROPYL-2-NITROANILINE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 4-isopropyl-2-nitroaniline from 2,2,2-trifluoro-N-(2-nitro-4-isopropylphenyl)acetamide was as follows: to a stirring solution of 2,2,2-trifluoro-N-(4-isopropyl-2-nitrophenyl)acetamide (2.1 g, 7.6 mmol) in methanol (40 mL) was added sequentially water (20 mL) and potassium carbonate ( 0.5 g, 4 mmol). The reaction mixture was stirred at room temperature for 18 h, followed by partition extraction with ethyl acetate (50 mL) and saturated saline (50 mL). After separation of the organic layer, the aqueous layer was then extracted with ethyl acetate (3 x 25 mL). All organic layers were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (silica gel 230-400 mesh, 150 g, eluting sequentially with 20% and 30% ethyl acetate/hexane solvent mixture) to afford 4-isopropyl-2-nitroaniline 1.18 g (61% yield) as an orange oil. Its NMR hydrogen spectrum (CDCl3) data were as follows: δ 1.23 (6H, d), 2.85 (1H, m), 6.77 (1H, d), 7.28 (1H, dd), 7.96 (1H, d). Mass spectrometry (ESI+) showed the molecular ion peak m/z 181.2 ([M+H]+). The HPLC (Method D) retention time was 3.97 min.

References

[1] Patent: WO2011/126567, 2011, A1. Location in patent: Page/Page column 187

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