3,4-Dichlorobenzonitrile Chemical Properties

Melting point:

74-78 °C (lit.)

Boiling point:

129-130 °C(Press: 0.01 Torr)

Density 

1.40±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Water Solubility 

Insoluble in water

form 

Powder or Crystalline Powder

color 

White to brown

BRN 

2326352

InChI

InChI=1S/C7H3Cl2N/c8-6-2-1-5(4-10)3-7(6)9/h1-3H

InChIKey

KUWBYWUSERRVQP-UHFFFAOYSA-N

SMILES

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

LogP

2.8 at 21.5℃

CAS DataBase Reference

6574-99-8(CAS DataBase Reference)

NIST Chemistry Reference

3,4-Dichlorobenzonitrile(6574-99-8)

Safety Information

Hazard Codes 

Xn,T,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

RIDADR 

3276

WGK Germany 

2

Hazard Note 

Irritant/Toxic

TSCA 

N

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

MSDS

• Language:English Provider:3,4-Dichlorobenzonitrile
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3,4-Dichlorobenzonitrile Usage And Synthesis

Chemical Properties

White solid

Uses

3,4-Dichlorobenzonitrilemay be used in the preparation of:

• 3,4-difluorobenzonitrile
• 3-chloro-4-fluorobenzonitrile
• 5-chloromethyl-3-( 3,4-dichlorophenyl)isoxazole
• N-[3-(2-pyridyl)isoquinolin-1-yl]-3,4-dichlorobenzamidine

General Description

3,4-Dichlorobenzonitrile (3,4-DCBN) is an aromatic nitrile that can be prepared from 3,4-dichlorobenzamide.

Flammability and Explosibility

Not classified

Synthesis

GENERAL STEPS: 3,4-Dichlorobenzaldehyde (1.0 mmol, 1.0 eq.) was dissolved in 4 mL of aqueous solution containing acetic acid (1.0 mmol, 1.0 eq.) in a 10 mL round-bottomed flask at 0°C. The reaction was carried out at 50°C with stirring for 6 hours or monitored by thin-layer chromatography (TLC) until the reaction was complete. The reaction mixture was stirred at 50 °C for 6 h or monitored by thin layer chromatography (TLC) until the reaction was complete. Upon completion of the reaction, the reaction was quenched with 10% aqueous NaHCO3 (1 mL) and subsequently extracted with ethyl acetate (3 x 10 mL). The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated by rotary evaporator to give the crude product 3,4-dichlorobenzonitrile. The product was characterized directly unless further purification by automated silica gel fast chromatography was required to remove trace impurities (three embodiments).

Toxics Screening Level

The initial threshold screening level (ITSL) for 3,4-dichlorobenzonitrile is 2 μg/m3 based on an annual averaging time.

References

[1] Synthetic Communications, 2000, vol. 30, # 17, p. 3109 - 3114
[2] Journal of Chemical Research - Part S, 2001, # 5, p. 190 - 191
[3] Tetrahedron Letters, 2016, vol. 57, # 34, p. 3844 - 3847
[4] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 11, p. 2815 - 2824
[5] Synthetic Communications, 2002, vol. 32, # 23, p. 3621 - 3624

3,4-Dichlorobenzonitrile(6574-99-8)Related Product Information

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