4-Amino-3-chlorobenzonitrile Chemical Properties

Melting point:

102-105 °C(lit.)

Boiling point:

277.8±25.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

-0.22±0.10(Predicted)

color 

Light yellow to Brown to Dark green

BRN 

1817655

CAS DataBase Reference

21803-75-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36/37-36/37/39

RIDADR 

3276

WGK Germany 

3

Hazard Note 

Harmful/Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

MSDS

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

4-Amino-3-chlorobenzonitrile Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Definition

ChEBI: 4-Amino-3-chlorobenzonitrile is a member of benzenes and a nitrile.

Synthesis

Step 1: N-chlorosuccinimide (12.4 g, 93 mmol) was slowly added to a stirred solution of 4-aminobenzonitrile (10.0 g, 84.7 mmol) in acetonitrile (100 mL) at 90 °C. After the addition was completed, the reaction mixture was stirred continuously at 90 °C for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure. The concentrated residue was dissolved in 500 mL of dichloromethane and washed with 5% aqueous sodium hydroxide. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 4-amino-3-chlorobenzonitrile as a brown solid (12.2 g, 95% yield).1H NMR (300 MHz, CDCl3) δ 7.54 (d, J = 1.7 Hz, 1H), 7.35 (dd, J = 1.8,8.4 Hz, 1H), 6.77 (d, J = 8.5 Hz, 1H ), 4.63 (br s, 2H).

References

[1] Synlett, 1999, # 12, p. 1984 - 1986
[2] Patent: EP2766359, 2016, B1. Location in patent: Paragraph 0383
[3] Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7529 - 7537
[4] Organic Letters, 2008, vol. 10, # 1, p. 113 - 116
[5] Synthesis, 1985, # 6/7, p. 669 - 670

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