2-Amino-5-Methyl-Benzonitrile Chemical Properties

Melting point:

59-63 °C

Boiling point:

152°C/15mmHg(lit.)

Density 

1.10±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

soluble in Methanol

form 

Solid

pka

2.25±0.10(Predicted)

color 

White to Brown

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

RIDADR 

UN 3335

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

2926907090

2-Amino-5-Methyl-Benzonitrile Usage And Synthesis

Uses

2-Amino-5-methylbenzonitrile can be used in combination therapy to treat Mucopolysaccharidosis I.

Synthesis

5-Methyl-2-nitrobenzonitrile (1.92 g, 11.84 mmol) was added in batches to a mixed solution of concentrated hydrochloric acid (12 mL) and ethanol (EtOH, 12 mL) with SnCl2 (11.22 g, 59.2 mmol) in stirring. The temperature was controlled at 20-30 °C using an ice bath during the reaction. The reaction mixture was continued to be stirred at room temperature for 1 h. The reaction mixture was then poured into pre-cooled aqueous 6N NaOH solution (ca. 30 mL) and neutralized to pH 7. The product was extracted with ethyl acetate (EtOAc), followed by washing of the organic layer with brine, drying with anhydrous magnesium sulfate (MgSO4), and concentration to give the target product, 2-amino-5-methylbenzonitrile (1.56 g, 99% yield) as a yellowish brown solid. The structure of the product was analyzed by 1H NMR (400 MHz, DMSO-d6) δ 2.21 (s, 3H), 5.79 (bs, 2H), 6.68-6.71 (d, 1H), 7.10-7.13 (dd, 1H), 7.15 (s, 1H); 13C NMR (DMSO-d6) δ 20.13,93.99,116.12, 118.94,125.38,132.32,135.76,150.21; mass spectrum (MS) m/z 133 (MH+) confirmed.

References

[1] Patent: US2008/306053, 2008, A1. Location in patent: Page/Page column 60
[2] Tetrahedron, 1994, vol. 50, # 18, p. 5515 - 5525
[3] Patent: US2004/92739, 2004, A1. Location in patent: Page 4
[4] Journal of Heterocyclic Chemistry, 1987, vol. 24, # 2, p. 345 - 349
[5] Chemische Berichte, 1905, vol. 38, p. 3555

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