2,6-Dichloro-4-(trifluoromethyl)nicotinonitrile Chemical Properties

Melting point:

38 °C

Boiling point:

282.4±35.0 °C(Predicted)

Density 

1.63±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

crystals

pka

-6.82±0.10(Predicted)

color 

Colourless

CAS DataBase Reference

13600-42-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi,Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-26-36/37/39

RIDADR 

3439

HazardClass 

TOXIC

HS Code 

2933399990

2,6-Dichloro-4-(trifluoromethyl)nicotinonitrile Usage And Synthesis

Chemical Properties

yellow powder

Uses

3-Cyano-2,6-dichloro-4-trifluoromethylpyridine is used as a reagent in the synthesis of cyano(trifluoromethyl)aminopyridine derivatives which are used as androgen receptor antagonists for stimulating hair growth and reducing sebum production. 3-Cyano-2,6-dichloro-4-trifluoromethylpyridine is also used in the preparation of novel analogs of marine indole alkaloids which are used as potential anticancer agents.

Synthesis

GENERAL STEPS: In a 500 mL round bottom flask, 84.5 g (414 mmol) of 2,6-dihydroxy-3-cyano-4-(trifluoromethyl)pyridine, 400 g of phosphoryl chloride and 35 g of catalyst were added. The mixture was heated and refluxed for 20 h, during which the progress of the reaction was monitored by TLC. Upon completion of the reaction, the reflux unit was changed to a distillation unit to evaporate the excess phosphorus trichloride. The reaction mixture was slowly poured into an ice-water mixture and a white solid was precipitated. The solid was collected by filtration and dried to give 79.6 g of the target product 2,6-dichloro-3-cyano-4-(trifluoromethyl)pyridine in 79.78% yield.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 475 - 477
[2] Patent: CN107382848, 2017, A. Location in patent: Paragraph 0043; 0046-0047

2,6-Dichloro-4-(trifluoromethyl)nicotinonitrile(13600-42-5)Related Product Information

• 2-Chloro-5-chloromethylpyridine
• 2,6-Lutidine
• 4-Methylpyridine
• 3-Cyanopyridine
• Pyridine
• 4-(Trifluoromethyl)pyridine
• Azamethiphos
• Dichlorodimethylsilane
• Dichloroacetic acid
• 2-Chloro-4-(trifluoromethyl)pyridine
• Clopyralid
• 4-(Trifluoromethyl)nicotinonitrile
• 2,6-Dichloro-4-(trifluoromethyl)pyridine
• 2-Chloro-4-methylpyridine-3-carbonitrile
• 2,6-Dichloro-4-methylnicotinonitrile
• 2,6-Dichloro-3-methylpyridine
• 2,6-Dichloronicotinonitrile
• 2-Chloro-3-cyanopyridine