methyl 3-nitro-5-(trifluoromethyl)benzoate Chemical Properties

Boiling point:

283.2±40.0 °C(Predicted)

Density 

1.442±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Appearance

Light yellow to yellow Solid

Safety Information

HS Code 

2916399090

methyl 3-nitro-5-(trifluoromethyl)benzoate Usage And Synthesis

Synthesis

3-Nitro-5-(trifluoromethyl)benzoic acid (1 g, 4.25 mmol) was dissolved in methanol (15 mL) and concentrated sulfuric acid (5 drops) was added as a catalyst. The reaction mixture was heated to reflux for 48 hours. After completion of the reaction, methanol was removed by distillation under reduced pressure. The residue was dissolved in ethyl acetate (20 mL) and washed sequentially with 5% sodium carbonate solution (3 x 20 mL) and saturated saline (20 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford methyl 3-nitro-5-trifluoromethylbenzoate without further purification. The yield was 87% and the product was a colorless oil.1H NMR (500 MHz, CDCl3) δ 9.05 (t, J = 1.8 Hz, 1H), 8.68 (t, J = 1.8 Hz, 1H), 8.63 (s, 1H), 4.05 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 163.62, 148.47, 133.16, 132.83 (q, J = 34.7 Hz), 131.87 (q, J = 3.5 Hz), 127.50, 124.42 (q, J = 3.8 Hz), 122.37 (q, J = 273.2 Hz), 53.26.

References

[1] Patent: WO2012/37132, 2012, A1. Location in patent: Page/Page column 47
[2] Patent: US2012/71489, 2012, A1. Location in patent: Page/Page column 59
[3] Patent: WO2017/125530, 2017, A1. Location in patent: Page/Page column 283
[4] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 12, p. 4158 - 4181
[5] Patent: WO2014/141187, 2014, A1. Location in patent: Page/Page column 119

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