5-METHYL-2-NITROBENZONITRILE Chemical Properties

Melting point:

92 °C

Boiling point:

338.9±30.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Appearance

Off-white to yellow Solid

Safety Information

HS Code 

2926907090

5-METHYL-2-NITROBENZONITRILE Usage And Synthesis

Synthesis

Phosphorus trichloride (16.96 mL, 1.1 eq.) was slowly added to a solution of N,N-dimethylformamide (329.6 mL) of 5-methyl-2-nitrobenzamide (29.8 g, 0.165 mol) via syringe over a period of 20 minutes. The reaction mixture was stirred at 25 °C for 40 min, followed by heating to 100 °C and continued stirring for 15 min. Upon completion of the reaction, the mixture was slowly poured into ice (750 g) and the pH of the aqueous solution was adjusted to 9-10 with ammonia (75 mL).The aqueous layer was extracted with ethyl acetate (1000 mL, followed by 2 x 600 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 2-nitro-5-methylbenzonitrile (25.7 g, 96% yield) as a yellow solid, which could be used in subsequent reactions without further purification. The purity of the product was confirmed by 1H NMR: 1H NMR (CDCl3) δ 2.54 (s, 3H, CH3), 7.59 (d, J = 8.4 Hz, 1H, Ar-H), 7.71 (s, 1H, Ar-H), 8.24 (d, J = 8.4 Hz, 1H, Ar-H).

References

[1] Patent: US2004/92739, 2004, A1. Location in patent: Page 4
[2] Patent: US2009/253719, 2009, A1. Location in patent: Page/Page column 19-20
[3] Tetrahedron, 1994, vol. 50, # 18, p. 5515 - 5525
[4] Medicinal Chemistry Research, 1999, vol. 9, # 3, p. 176 - 185
[5] Patent: US2010/260825, 2010, A1. Location in patent: Page/Page column 4

5-METHYL-2-NITROBENZONITRILE(64113-86-6)Related Product Information

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• 2-Chloro-5-nitrobenzonitrile
• 2-Amino-5-Methyl-Benzonitrile
• 2-Nitrobenzonitrile
• 2-Nitro-5-(trifluoromethyl)benzonitrile
• 4,5-dimethyl-2-nitrobenzonitrile
• 3-cyano-4-nitrobenzoic acid
• 5-METHYL-2-NITROBENZONITRILE