ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Cyanopyridine 2-Chloro-4-cyanopyridine

2-Chloro-4-cyanopyridine

Product Name2-Chloro-4-cyanopyridine
CAS33252-30-1
MFC6H3ClN2
MW138.55
EINECS608-852-0
MOL File33252-30-1.mol

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
Storage Class	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English
ALFA	English

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.

Materials Uses

2-Chloro-4-cyanopyridine is employed in the formulation of advanced materials, including polymers and coatings, offering improved durability and chemical resistance compared to similar compounds.

Synthesis

14906-59-3

33252-30-1

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

Chemical Properties

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MSDS

Usage And Synthesis

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