4-Amino-3-methylbenzonitrile Chemical Properties

Melting point:

93-94°C

Boiling point:

304.5±30.0 °C(Predicted)

Density 

1.10±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

1.58±0.10(Predicted)

color 

White to Gray to Brown

BRN 

3235728

InChIKey

MBZDCUMFFPWLTJ-UHFFFAOYSA-N

CAS DataBase Reference

78881-21-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-43-20/21-36/37/38

Safety Statements 

22-36/37/39-36/37-26-9

RIDADR 

3276

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

MSDS

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4-Amino-3-methylbenzonitrile Usage And Synthesis

Uses

4-Amino-3-methylbenzonitrile is a useful research chemical used in organic synthesis and other chemical processes.

Chemical Properties

Light yellow powder

Synthesis

General procedure for the synthesis of 4-amino-3-methylbenzonitrile from 3-methyl-4-nitrobenzonitrile: 9.89 g (61 mmol, 1 equiv.) of 3-methyl-4-nitrobenzonitrile was added to a stirred 100 mL tetrahydrofuran (THF) solution at room temperature. Subsequently, 1 g of 10% palladium carbon catalyst was added. Next, 25 mL of methanol was added. The reaction system was placed in a hydrogenation unit and the reaction was carried out at a hydrogen pressure of 50 psi. When hydrogen consumption was no longer observed, the reaction was stopped and filtered through diatomaceous earth to remove the catalyst. The product was purified by column chromatography using a 1:1 mixture of hexane and dichloromethane as the mobile phase. 7.5 g of 4-amino-3-methylbenzonitrile in beige powder form was finally obtained in 93% yield. The 1H-NMR (DMSO-d6) data of the product were as follows: δ 2.27 (3H, s), 6.06 (2H, s), 6.41 (1H, d), 6.46 (1H, s), 7.30 (1H, d).

References

[1] Journal of Medicinal Chemistry, 1999, vol. 42, # 18, p. 3572 - 3587
[2] Patent: US2017/44373, 2017, A1. Location in patent: Paragraph 0227; 0228
[3] Patent: US6353006, 2002, B1. Location in patent: Page column 23
[4] Patent: US2005/54655, 2005, A1. Location in patent: Page/Page column 15
[5] Patent: US2004/44203, 2004, A1. Location in patent: Page 27

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