3,5-Dichlorobenzonitrile

3,5-Dichlorobenzonitrile Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H331Toxic if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

3,5-Dichlorobenzonitrile Chemical Properties,Usage,Production

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