Chemical Properties
white to light yellow crystal powder
Uses
4-Methyl-3-nitrobenzonitrile may be used in the synthesis of (
E)-1-(4-cyano-2-nitrophenyl)-2-(4-(4-cyanophenoxy)phenyl)ethene and (
E)-1-(4-fluorophenyl)-2-(4-cyano-2-nitrophenyl)ethene.
Uses
2-Nitro-p-toluonitrile (cas# 939-79-7) is a compound useful in organic synthesis.
Synthesis
A. Synthesis of 4-methyl-3-nitrobenzonitrile. Nitric acid (20 mL) was slowly added dropwise to a mixture of 4-methylbenzonitrile (11 g, 0.098 mol) with concentrated sulfuric acid (20 mL) over a period of 1 hour at 0°C. After the dropwise addition was completed, the reaction mixture was continued to be stirred at 0°C for 1 hour. Subsequently, the reaction mixture was carefully poured into crushed ice to quench the reaction. The precipitate precipitated was collected by filtration to afford 4-methyl-3-nitrobenzonitrile (15.2 g, 95% yield) as a white solid. The product was characterized by 1H NMR (500 MHz, CDCl3): δ 8.27 (d, J = 1.6 Hz, 1H), 7.78 (dd, J = 8.0,1.7 Hz, 1H), 7.51 (d, J = 8.0 Hz, 1H), 2.69 (s, 3H).
References
[1] Patent: US2005/38032, 2005, A1. Location in patent: Page/Page column 29
[2] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 8, p. 1203 - 1208
[3] Journal of the Chemical Society, 1924, vol. 125, p. 2288
[4] Journal of the American Chemical Society, 1925, vol. 47, p. 1394
[5] Chemische Berichte, 1918, vol. 51, p. 561
