2-Chloro-3-pyridinecarboxaldehyde Chemical Properties

Melting point:

50-54 °C (lit.)

Boiling point:

119 °C(Press: 30 Torr)

Density 

1.332±0.06 g/cm3(Predicted)

Flash point:

>230 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, DMSO

form 

Powder or Low Melting Solid

pka

-1.36±0.10(Predicted)

color 

White to off-white

InChI

InChI=1S/C6H4ClNO/c7-6-5(4-9)2-1-3-8-6/h1-4H

InChIKey

KHPAGGHFIDLUMB-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC=C1C=O

CAS DataBase Reference

36404-88-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36-43

Safety Statements 

26-36/37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

2-Chloro-3-pyridinecarboxaldehyde Usage And Synthesis

Chemical Properties

Brown Solid

Uses

Starting material for the preparation of 5-azaindoles by the Hemetsberger-Knittel reaction involving the thermal decomposition of alkenyl azides.1

Uses

Azaindazole intermediate.

Synthesis

General procedure for the synthesis of 2-chloro-3-pyridinecarboxaldehyde from 2-chloro-3-pyridinemethanol: The hydrolyzed product was transferred to a four-necked flask, 300 g of ethyl acetate and 0.8 g of TEMPO were added, and the mixture was stirred and cooled to 0 °C. Subsequently, 450 g of freshly prepared sodium hypochlorite solution (pH=11, 10% active chlorine) was slowly added dropwise, and the reaction temperature was controlled at 0-5 °C. After the dropwise addition, the reaction system was warmed up to room temperature and stirred continuously for 1 hour to ensure complete reaction. Post-treatment steps: the reaction mixture was allowed to stand and layered, the ethyl acetate phase was separated, washed with water, dried with anhydrous magnesium sulfate, concentrated and then cooled and crystallized to give 79 g of the light yellow crystalline product 2-chloro-3-pyridinecarboxaldehyde, with a purity of 98.2%, and based on the yield of 2-chloro-3-chloromethylpyridine was 89.6%.

References

[1] Patent: CN107501171, 2017, A. Location in patent: Paragraph 0028; 0034; 0035; 0036; 0037; 0044; 0045-0047
[2] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 5, p. 1595 - 1597
[3] Synthetic Communications, 2008, vol. 38, # 6, p. 889 - 904
[4] Synthesis, 2010, # 20, p. 3439 - 3448
[5] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 5, p. 694 - 707

2-Chloro-3-pyridinecarboxaldehyde(36404-88-3)Related Product Information

• 3-Bromo-2-chloropyridine
• Epichlorohydrin
• 2-Chloro-5-chloromethylpyridine
• 3-Aminopyridine
• 3-Pyridinecarboxaldehyde
• 4-Pyridinecarboxaldehyde
• 2-Chloro-3-fluoropyridine
• 2-Chloro-3-iodopyridine
• 3-Hydroxypyridine
• 2-Pyridinecarboxaldehyde
• Clopidol
• Pentachloropyridine
• 2-Chloro-3-cyanopyridine
• 2-CHLORO-4,6-DIMETHYLNICOTINAMIDE
• 2,6-Dichloronicotinic acid
• 2-Chloronicotinyl chloride
• 2-Chloronicotinamide
• 2-Chloronicotinic acid