3,5-Dichlorobenzonitrile Chemical Properties

Melting point:

64-66 °C (lit.)

Boiling point:

283.76°C (rough estimate)

Density 

1.4980 (rough estimate)

refractive index 

1.6000 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol (Slightly)

form 

Crystalline Powder

color 

White to beige-brownish

BRN 

2207019

InChI

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

InChIKey

PUJSUOGJGIECFQ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

6575-00-4(CAS DataBase Reference)

NIST Chemistry Reference

3,5-Dichlorobenzonitrile(6575-00-4)

Safety Information

Hazard Codes 

Xn,T,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-37/39-36/37/39-22-36-36/37-9

RIDADR 

3276

WGK Germany 

3

Hazard Note 

Irritant/Toxic

TSCA 

N

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

MSDS

• Language:English Provider:3,5-Dichlorobenzonitrile
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3,5-Dichlorobenzonitrile Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

3,5-Dichlorobenzonitrile was used as internal standard during the programmed temperature vaporization-GC-MS determination of dichlobenil and 2,6-dichlorobenzamide in onions.

Synthesis

General procedure for the synthesis of 3,5-dichlorobenzonitrile from 3,5-dichloro-1-bromobenzene: iPrMgCl (2M in THF, 4.1 mL) and THF (5 mL) were added to a flask containing dry LiCl (0.35 g, 8.24 mmol) at 15 °C. After stirring for 15 min, a solution of 3,5-dichloro-1-bromobenzene (1.46 g, 8.03 mmol) in THF (1 mL) was slowly added to the reaction mixture and stirring was continued for 15 min. Subsequently, the reaction mixture was cooled to 0 °C, DMF (1.3 mL, 12 mmol) was added and stirred at this temperature for 2 hours. Upon completion of the reaction, aqueous NH3 (7 mL, 28-30%) and I2 (4.06 g, 16 mmol) were sequentially added to the mixture. After stirring for 2 h at room temperature, the reaction mixture was poured into saturated aqueous Na2SO3 solution and extracted with CHCl3 (3 x 30 mL). The organic layers were combined, dried with Na2SO4 and filtered. After removing the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 9:1, v/v) to afford pure 3,5-dichlorobenzonitrile (0.73 g) in 71% yield. Most of the nitrile compounds involved in this study were commercially available and were identified by comparison with real samples.

References

[1] Tetrahedron, 2013, vol. 69, # 5, p. 1462 - 1469

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