4-Chloro-3-nitrobenzonitrile Chemical Properties

Melting point:

98-100 °C (lit.)

Boiling point:

284.8±25.0 °C(Predicted)

Density 

1.6133 (rough estimate)

refractive index 

1.5557 (estimate)

storage temp. 

Sealed in dry,Room Temperature

Water Solubility 

Slightly soluble in water

form 

powder to crystal

color 

White to Light yellow to Green

BRN 

1639111

InChI

InChI=1S/C7H3ClN2O2/c8-6-2-1-5(4-9)3-7(6)10(11)12/h1-3H

InChIKey

XBLPHYSLHRGMNW-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

939-80-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-36/37

WGK Germany 

2

RTECS 

DI3050000

HS Code 

29269090

MSDS

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

4-Chloro-3-nitrobenzonitrile Usage And Synthesis

Chemical Properties

light yellow crystalline powder

Uses

4-Chloro-3-nitrobenzonitrile may be used in the synthesis of 3-nitro-4-thiocyanobenzonitryl.

General Description

FT-IR and μ-Raman spectra of 4-chloro-3-nitrobenzonitrile have been recorded in the range of 400-4000cm^-1 and 100-4000cm^-1, respectively. It has been prepred from the reaction of 4-chloro-3-nitrobenzamide and phosphorus oxychloride. Crystal structure of 4-chloro-3-nitrobenzonitrile has been reported. Molecules of 4-chloro-3-nitrobenzonitrile are linked by weak intermolecular C-H…O and C-H…N hydrogen bonds.

Synthesis

The general procedure for the synthesis of 4-chloro-3-nitrobenzonitrile from 4-chlorobenzonitrile was as follows: 4-chlorobenzonitrile (4 g, 29.2 mmol) was dissolved in 40 mL of anhydrous acetonitrile, and nitronium tetrafluoroborate (7.7 g, 58.39 mmol) was added slowly at 0 °C. The reaction mixture was stirred at room temperature for 20 hours. After completion of the reaction, the mixture was quenched by pouring it into cold water. The precipitated white solid product was collected by filtration and the filter cake was washed with cold water to remove impurities. The resulting crude product (4.0 g, 75.47% yield) could be used directly in the subsequent reaction steps without further purification.

References

[1] Journal of Medicinal Chemistry, 1990, vol. 33, # 4, p. 1252 - 1257
[2] Patent: WO2014/24056, 2014, A1. Location in patent: Page/Page column 40
[3] MedChemComm, 2017, vol. 8, # 10, p. 2003 - 2011
[4] Journal of Medicinal Chemistry, 1991, vol. 34, # 3, p. 1110 - 1116
[5] Recueil des Travaux Chimiques des Pays-Bas, 1922, vol. 41, p. 36

4-Chloro-3-nitrobenzonitrile(939-80-0)Related Product Information

• 2-CHLORO-6-NITROBENZONITRILE,6-CHLORO-2-NITROBENZONITRILE
• 5-CHLORO-2-NITROBENZONITRILE 97%,5-CHLORO-2-NITROBENZONITRILE,3-Chloro-6-nitrobenzonitrile
• 4-CHLORO-2-NITROBENZONITRILE
• 2-CHLORO-4-NITROBENZONITRILE
• 2-AMINO-3-CHLORO-5-NITROBENZONITRILE
• 2-CHLORO-5-NITROBENZONITRILE
• 4-Chlorobenzonitrile
• 3-AMINO-4-CHLOROBENZONITRILE
• 4-Chloro-3-nitrotoluene
• 4-CHLORO-3,5-DINITROBENZONITRILE
• 3-NITROBENZONITRILE
• 4-Chloro-3-nitrobenzonitrile
• 2,6-DICHLORO-3-NITROBENZONITRILE
• 3-Aminobenzonitrile
• 3-Chloro-5-nitrobenzonitrile 98%,3-CHLORO-5-NITROBENZONITRILE
• 3-Nitrobenzonitrile
• 2-CHLORO-3-NITROBENZONITRILE
• 3-Chloro-2-nitrobenzonitrile