3-CHLORO-4-METHYLBENZONITRILE Chemical Properties

Melting point:

45-48 °C (lit.)

Boiling point:

106°C/6mm

Density 

1.19

Flash point:

183 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Light yellow

InChI

InChI=1S/C8H6ClN/c1-6-2-3-7(5-10)4-8(6)9/h2-4H,1H3

InChIKey

INEMHABDFCKBID-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

21423-81-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

11

Safety Statements 

36

RIDADR 

UN 1325 4.1/PG 2

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2926907090

MSDS

• Language:English Provider:SigmaAldrich

3-CHLORO-4-METHYLBENZONITRILE Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

3-Chloro-4-methylbenzonitrile may be used in chemical synthesis studies.

Synthesis

In a 1L four-neck flask, 161.4 g of dimethyl 2-(4-cyano-2-chlorophenyl)-1,3-malonate (1 eq.), 21.7 g of water (2 eq.), and 140.9 g of 95% anhydrous calcium chloride (2 eq.) were added to 606 g of N,N-dimethylacetamide. The reaction was stirred and heated to 140-145°C and kept at this temperature for 20-24 hours. After completion of the reaction, cooled to 30 °C, 352.5 g of water and 303 g of dichloromethane were added. About 70.2 g of concentrated hydrochloric acid was added slowly and the pH of the system was adjusted to 5-7. After partitioning, the aqueous layer was extracted with dichloromethane and the organic phases were combined. The organic phase was concentrated under reduced pressure to give a solution of N,N-dimethylacetamide containing 3-chloro-4-methylbenzonitrile. Vacuum distillation was continued to collect 3-chloro-4-methylbenzonitrile until no product evaporated, resulting in 75.9 g of white solid in 83.0% yield.

References

[1] Patent: CN107673994, 2018, A. Location in patent: Paragraph 0135; 0136; 0137

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