3-Chloro-4-cyanopyridine Chemical Properties

Melting point:

71-73°C

Boiling point:

233.3±20.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

Dichloromethane, Ethyl Acetate, Methanol

form 

Solid

pka

-0.41±0.18(Predicted)

color 

Pale Yellow

InChI

InChI=1S/C6H3ClN2/c7-6-4-9-2-1-5(6)3-8/h1-2,4H

InChIKey

JLLJPPBGJVCFGG-UHFFFAOYSA-N

SMILES

C1=NC=CC(C#N)=C1Cl

CAS DataBase Reference

68325-15-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37

RIDADR 

UN3439

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

3-Chloro-4-cyanopyridine Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

3-Chloro-4-cyanopyridine (cas# 68325-15-5) is a compound useful in organic synthesis.

Synthesis

The general procedure for the synthesis of 3-chloro-4-cyanopyridine from 4-cyanopyridine was as follows: to a stirred solution of 2,2,6,6-tetramethylpiperidine (17.16 mL, 100.854 mmol) in tetrahydrofuran (THF, 100 mL) at -30 °C was slowly added n-butyllithium (n-BuLi, 2.17 M, 44.26 mL, 96.052 mmol). The reaction mixture was stirred at 25 °C for 15 min before being cooled to -78 °C and a solution of 4-cyanopyridine (5 g, 48.026 mmol) in THF (40 mL) was added slowly and dropwise. After continued stirring at -78 °C for 30 min, a THF (50 mL) solution of hexaethyl ethane (23.87 g, 100.854 mmol) was added. The resulting mixture was stirred at -78 °C for 30 min, followed by quenching the reaction with saturated ammonium chloride (NH4Cl) solution. Water (100 mL) was added to the reaction mixture and extracted with ethyl acetate (4 x 300 mL). The organic layers were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography using silica gel (100-200 mesh) and 5% ethyl acetate-hexane as eluent to yield 3-chloropyridine-4-carbonitrile (3.5 g, 25.26±1 mmol, 53% yield) as a light-white solid.The GC-MS analysis showed the molecular ion peak to be 138 m/z. The molecular ions were analyzed by GC-MS.

References

[1] Tetrahedron, 2006, vol. 62, # 25, p. 5862 - 5867
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 10118 - 10129
[3] Patent: WO2014/186035, 2014, A1. Location in patent: Page/Page column 182; 183
[4] Tetrahedron Letters, 2005, vol. 46, # 1, p. 135 - 137
[5] Journal of the American Chemical Society, 2013, vol. 135, # 24, p. 9213 - 9219

3-Chloro-4-cyanopyridine(68325-15-5)Related Product Information

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• 2,6-Dichloroisonicotinonitrile
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• 2-Cyano-4-chloropyridine, 4-Chloro-2-cyanopyridine, 4-Chloropicolinonitrile,4-CHLORO-2-CYANOPYRIDINE
• 2,3,5,6-TETRACHLOROISONICOTINONITRILE