5-AMINO-2-METHYLBENZONITRILE Chemical Properties

Melting point:

88-91 °C(lit.)

Boiling point:

110°C/22mmHg(lit.)

Density 

1.1083 (rough estimate)

refractive index 

1.6231 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

Powder

color 

Yellow to brown

InChIKey

YDZVQWCVKXYGIU-UHFFFAOYSA-N

CAS DataBase Reference

50670-64-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN 3439 6.1/PG III

WGK Germany 

3

Hazard Note 

Toxic

HazardClass 

IRRITANT

HazardClass 

6.1

PackingGroup 

III

HS Code 

2926907090

MSDS

• Language:English Provider:SigmaAldrich

5-AMINO-2-METHYLBENZONITRILE Usage And Synthesis

Uses

5-Amino-2-methylbenzonitrile may be used as a starting material for the synthesis of 5-iodo-2-methylbenzonitrile and 5-hydroxy-2-methylbenzonitrile. It may also be used in the preparation of 5-(2,4-dioxothiazolidin-3-yl)-2-methylbenzonitrile by reacting with thioglycolic acid methyl ester in the presence of 1,1′-carbonyldiimidazole.

Synthesis

Step 2: Synthesis of 5-amino-2-methylbenzonitrile: 2-methyl-5-nitrobenzonitrile (25.0 g, 154 mmol), 10% palladium carbon catalyst (2.5 g), ethyl acetate (150 mL) and ethanol (150 mL) were mixed. The reaction mixture was stirred under hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by filtration through a pad of diatomaceous earth followed by concentration of the filtrate to afford 5-amino-2-methylbenzenecarbonitrile (19.6 g, 96% yield), the product was a tan solid. Mass spectral analysis showed m/e = 133 (M + H). Reference: Scholz, D. et al, J. Med. Chem. 41, 1050-1059 (1998).

References

[1] Patent: WO2005/97750, 2005, A1. Location in patent: Page/Page column 69
[2] Organic Letters, 2017, vol. 19, # 18, p. 4746 - 4749
[3] Organic Letters, 2003, vol. 5, # 7, p. 1131 - 1134
[4] Journal of Materials Chemistry, 2011, vol. 21, # 26, p. 9523 - 9531
[5] Patent: US5596006, 1997, A

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