3-Amino-4-methylbenzonitrile Chemical Properties

Melting point:

81 °C

Boiling point:

312.8±22.0 °C(Predicted)

Density 

1.10±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

2?+-.0.10(Predicted)

form 

crystals

color 

White to off white to clear shards

InChI

InChI=1S/C8H8N2/c1-6-2-3-7(5-9)4-8(6)10/h2-4H,10H2,1H3

InChIKey

IEWMNQUBZPVSSV-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=C(C)C(N)=C1

CAS DataBase Reference

60710-80-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

3276

Hazard Note 

Toxic

HazardClass 

IRRITANT

HS Code 

2926907090

3-Amino-4-methylbenzonitrile Usage And Synthesis

Chemical Properties

off-white crystalline

Uses

3-Amino-4-methylbenzonitrile is an organic compound commonly used as an intermediate in organic synthesis, especially in pharmaceutical and pesticide chemistry.

Synthesis

C.14.b. Synthesis of 3-amino-4-methylbenzonitrile: 120 g of 3-nitro-4-methylbenzonitrile was suspended in 1.2 L of ethanol, and 7 g of 10% Pd/C catalyst was added and the hydrogenation reaction was carried out in a 50 L hydrogen atmosphere at room temperature. Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration, followed by distillation under reduced pressure to remove the solvent to afford 95 g of pure 3-amino-4-methylbenzonitrile in 97% yield. The product was characterized by 1H-NMR (DMSO-d6; δ, ppm): 7.1 (dd, 1H); 6.90 (d, 1H); 6.85 (d, 1H); 5.35 (s, 2H, NH2); 2.15 (s, 3H).

References

[1] Patent: US6455671, 2002, B1
[2] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 8, p. 1203 - 1208
[3] Chemische Berichte, 1903, vol. 36, p. 4359
[4] Chemische Berichte, 1904, vol. 37, p. 1845
[5] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 1997, vol. 53, # 2, p. 141 - 150

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