2-Chloro-5-pyridineacetonitrile Chemical Properties

Melting point:

49-54°C

Boiling point:

182 °C(Press: 1 Torr)

Density 

1.262±0.06 g/cm3(Predicted)

Flash point:

>110℃

storage temp. 

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

form 

solid

pka

-1.02±0.10(Predicted)

Appearance

Brown to reddish brown Solid

InChI

InChI=1S/C7H5ClN2/c8-7-2-1-6(3-4-9)5-10-7/h1-2,5H,3H2

InChIKey

BLGUCBUETMYJTB-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=CC=C1CC#N

CAS DataBase Reference

39891-09-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T,Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

RIDADR 

UN 3439 6.1 / PGIII

WGK Germany 

3

HazardClass 

IRRITANT, TOXIC

HS Code 

2933399990

2-Chloro-5-pyridineacetonitrile Usage And Synthesis

Uses

2-Chloro-5-cyanomethylpyridine

Synthesis

General procedure for the synthesis of 2-chloro-5-pyridylacetonitrile from 2-chloro-5-chloromethylpyridine and sodium cyanide: Step 1. Synthesis of (6-chloropyridin-3-yl)acetonitrile. To a stirred solution of 2-chloro-5-chloromethylpyridine (25 g, 0.154 mol) in ethanol (40 mL) was slowly added an aqueous solution of sodium cyanide (8.17 g, 0.167 mol) (18 mL) at 0 °C. The reaction mixture was heated to reflux for 2 hours, followed by continued stirring at room temperature for 18 hours. Upon completion of the reaction, the solvent was removed by vacuum evaporation and the residue was dissolved in water and extracted with dichloromethane (500 mL). The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography with the eluent being a 70/30 dichloromethane/hexane solvent mixture to give 20 g (85% yield) of brown oily product. The product was solidified by standing and ESI-MS m/z 153 (MH+).

References

[1] Patent: WO2010/130708, 2010, A1. Location in patent: Page/Page column 105
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 7, p. 2168 - 2173
[3] Patent: WO2013/13817, 2013, A1. Location in patent: Page/Page column 111
[4] Patent: WO2013/13815, 2013, A1. Location in patent: Page/Page column 221
[5] Patent: US2013/29961, 2013, A1. Location in patent: Paragraph 0705

2-Chloro-5-pyridineacetonitrile(39891-09-3)Related Product Information

• Pentachloropyridine
• 2-Chloro-5-fluoropyridine
• Epichlorohydrin
• 2-Chloro-3-cyanopyridine
• Pyridine
• 2-Pyridylacetonitrile
• 2,6-Lutidine
• 2-Chloro-5-chloromethylpyridine
• Chloroacetonitrile
• Clopidol
• Glycolonitrile
• Chloroacetic acid
• Benzeneacetonitrile
• 2-Chloropyridine
• Difluorochloromethane
• acetonitrile
• 3-PYRIDYLACETONITRILE
• 4,6-Dichloropyridine-3-acetonitrile