4-Amino-3-nitrobenzonitrile Chemical Properties

Melting point:

159-162 °C (lit.)

Boiling point:

349.8±32.0 °C(Predicted)

Density 

1.41±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Soluble in ethanol and benzene.

pka

-3.52±0.10(Predicted)

form 

Powder, Crystals or Crystalline Powder

color 

Yellow

BRN 

778939

InChI

InChI=1S/C7H5N3O2/c8-4-5-1-2-6(9)7(3-5)10(11)12/h1-3H,9H2

InChIKey

JAHADAZIDZMHOP-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=C(N)C([N+]([O-])=O)=C1

CAS DataBase Reference

6393-40-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-36/37/39

RIDADR 

3276

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

MSDS

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

4-Amino-3-nitrobenzonitrile Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

4-Amino-3-nitrobenzonitrile is used in gamma irradiations effect on release of this compound from polyanhydride matrixes.

Uses

Gamma irradiations effect on release of 4-amino-3-nitrobenzonitrile from polyanhydride matrixes.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 36, p. 1746, 1993 DOI: 10.1021/jm00064a008

Synthesis

General procedure for the synthesis of 4-amino-3-nitrobenzonitrile from 4'-cyanoacetanilide: potassium nitrate (15.6 mmol) was dissolved in 8 mL of concentrated sulfuric acid and the mixture was cooled to below 0 °C. Under this cooling condition, 7.8 mmol of 4'-cyanoacetanilide was slowly added, keeping the reaction temperature at 0 °C for 3.5 hours. Upon completion of the reaction, the mixture was poured into an ice water bath and the resulting yellow solid was collected by filtration and washed with a small amount of cold water. Subsequently, the resulting product was suspended in 30 mL of 2 mol/L sulfuric acid solution and heated under reflux conditions for 3 hours. At the end of the reaction, the suspension was cooled to room temperature, and the yellow solid was again collected by filtration and washed with a small amount of cold water to finally obtain the target product 4-amino-3-nitrobenzonitrile in 74% yield.

References

[1] Journal of the Brazilian Chemical Society, 2018, vol. 29, # 6, p. 1304 - 1317
[2] Journal of the Chemical Society, 1950, p. 1722,1725
[3] Journal of Medicinal Chemistry, 1995, vol. 38, # 10, p. 1786 - 1792
[4] Australian Journal of Chemistry, 1994, vol. 47, # 2, p. 247 - 262
[5] Journal of Medicinal Chemistry, 1993, vol. 36, # 12, p. 1746 - 1753

4-Amino-3-nitrobenzonitrile(6393-40-4)Related Product Information

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