2-Chloro-4-cyanopyridine Chemical Properties

Melting point:

69-73 °C(lit.)

Boiling point:

104-106°C 15mm

Density 

1.33±0.1 g/cm3(Predicted)

Flash point:

104-106°C/15mm

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

-1.60±0.10(Predicted)

color 

White to Almost white

BRN 

113927

InChI

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

InChIKey

QRXBTPFMCTXCRD-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

33252-30-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-36/37/39-36/37

RIDADR 

3276

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Chloro-4-cyanopyridine Usage And Synthesis

Chemical Properties

White to off-white solid

Uses

2-Chloro-4-cyanopyridine is an intermediate used to prepare pyrrolopyridine inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2). It is also used to synthesize pyridinyl-tetrazoles as scaffold to identify matrix MMP-13 inhibitors for treatment of osteoarthritis.

Synthesis

The general procedure for the synthesis of 2-chloro-4-cyanopyridine from 4-cyanopyridine N-oxide was as follows: 120 g of 4-cyanopyridine-N-oxide, 360 mL of 1,2-dichloroethane, and 183.6 g of phosphorochloridic acid were added sequentially in a 1000 mL three-necked reaction flask. After the reaction system was cooled to -2±2°C, 151.5 g of triethylamine was added slowly dropwise for a controlled dropwise time of 2 hours. After the dropwise addition, the reaction was continued at the same temperature with stirring for 2 hours. Upon completion of the reaction, the reaction solution was concentrated by reduced pressure distillation until no fractions flowed out. 240 mL of water was added to the concentrated solution and a large amount of solid was precipitated after thorough stirring. The solid was collected by filtration and the filter cake was washed with appropriate amount of water to obtain 117.5 g of white solid product 2-chloro-4-cyanopyridine.

References

[1] Tetrahedron Letters, 2001, vol. 42, # 39, p. 6815 - 6818
[2] Patent: CN104945383, 2017, B. Location in patent: Paragraph 0031; 0035; 0036

2-Chloro-4-cyanopyridine(33252-30-1)Related Product Information

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• 3-CHLORO-4-CYANOPYRIDINE,3-Chloro-4-cyanopyridine ,98%
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• 2-CHLORO-3-CYANOPYRIDINE-4-BORONIC ACID
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• 2-chloro-5-cyanopyridine