2-Amino-4-methylbenzonitrile Chemical Properties

Melting point:

92-95 °C (lit.)

Boiling point:

150-152 °C(Press: 15 Torr)

Density 

1.10±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

Powder

pka

1.94±0.10(Predicted)

color 

Light yellow to Yellow to Orange

CAS DataBase Reference

26830-96-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,T

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36-36/37

RIDADR 

3439

WGK Germany 

3

Hazard Note 

Toxic

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Amino-4-methylbenzonitrile Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

2-Amino-4-methylbenzonitrile was used in the synthesis of:

• 7-methyl-4-(phenylamino)quinazoline-2(1H)-selone
• racemic aminoquinolines, potential acetylcholinesterase (AChE) inhibitors

Synthesis

a) Synthesis of 2-amino-4-methylbenzonitrile 4-Methyl-2-nitrobenzonitrile (4.9 g, 30 mmol) was mixed with 10% palladium-carbon catalyst (500 mg) in 1,4-dioxane (60 mL), and the reaction was stirred overnight under a hydrogen atmosphere (balloon pressurized). Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration and the filtrate was concentrated under reduced pressure to give the crude product. The crude product was further purified by fast column chromatography (eluent: dichloromethane) to afford 2-amino-4-methylbenzonitrile as a light yellow solid (3.3 g, 83% yield). 1H-NMR (300 MHz, CDCl3) δ 7.26 (d, J = 8.3 Hz, 1H), 6.56 (s, 1H), 6.55 (s, 1H), 4.32 (br s, 2H), 2.29 (s, 3H).

References

[1] Chemical Communications, 2011, vol. 47, # 31, p. 8808 - 8810
[2] Journal of the Chemical Society, Perkin Transactions 2, 2001, # 2, p. 214 - 228
[3] Patent: US5891909, 1999, A
[4] Patent: EP906091, 2006, B1. Location in patent: Page/Page column 46
[5] Journal fuer Praktische Chemie (Leipzig), 1889, vol. <2> 40, p. 12

2-Amino-4-methylbenzonitrile(26830-96-6)Related Product Information

• ALTRENOGEST
• Glycine
• Benzonitrile
• N,N-Dimethyl-1,4-phenylenediamine
• 4-Nitrobenzonitrile
• p-Tolunitrile
• Lithium bis(trimethylsilyl)amide
• 2-Amino-4-methylbenzoic acid
• 2-Aminobenzonitrile
• 2-Cyanophenol
• Betaine
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• 4-Methyl-2-nitrobenzonitrile
• 2-NITRO-4-(TRIFLUOROMETHYL)BENZONITRILE
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• 4-AMINO-3-METHYLBENZONITRILE, 98+%,4-AMINO-3-METHYLBENZONITRILE
• 5-AMINO-2-METHYLBENZONITRILE
• ETHYL 4-CYANO-3-NITROBENZOATE