4-Chloronicotinic acid Chemical Properties

Melting point:

139-143 °C

Boiling point:

301.9±22.0 °C(Predicted)

Density 

1.470±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Soluble in organic solvents at 20°C

form 

powder

pka

0.78±0.25(Predicted)

color 

White

BRN 

9255849

InChIKey

IMRGVWZLCZERSQ-UHFFFAOYSA-N

CAS DataBase Reference

10177-29-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT, KEEP COLD

PackingGroup 

III

HS Code 

29333990

MSDS

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

4-Chloronicotinic acid Usage And Synthesis

Chemical Properties

White to light brown solid

Uses

4-Chloronicotinic Acid is a building block used in a synthesis of benzocanthinones via tributyltin hydride radical induced cyclization. It is also used in a synthesis of heterocyclic analogues of xanthone.

Uses

Building block used in a synthesis of benzocanthinones via tributyltin hydride radical induced cyclization. Also used in a synthesis of heterocyclic analogues of xanthone.

Synthesis

1. Neutralization reaction: Neutralize 4-chloropyridine hydrochloride using 10% NaOH solution to obtain 4-chloropyridine (1). 2. lithiation reaction: 4-chloropyridine (1) (15 mmol) was dissolved in THF (250 ml) under nitrogen protection, cooled to -78 °C, and 1.2 equivalents of lithium diisopropylammonium was slowly added (1.5 M hexane solution containing 1 equivalent of THF, ALDRICH). 3. carboxylation reaction: the resulting anion is reacted with dry CO? to produce 4-chloropyridine-3-carboxylic acid (3, i.e. 4-chloronicotinic acid). 4. Isolation and purification: The reaction mixture was treated and isolated to obtain 4-chloronicotinic acid as a colorless solid in 60-80% yield.

References

[1] Journal of Organic Chemistry, 1995, vol. 60, # 2, p. 292 - 296
[2] Patent: US2011/53975, 2011, A1. Location in patent: Page/Page column 60
[3] Patent: WO2009/87238, 2009, A2. Location in patent: Page/Page column 97; 98-99
[4] Patent: WO2005/21546, 2005, A1. Location in patent: Page/Page column 124-125
[5] Journal of Medicinal Chemistry, 2016, vol. 59, # 5, p. 1869 - 1879

4-Chloronicotinic acid(10177-29-4)Related Product Information

• 4-Chloropyridinium chloride
• 2-Picolinic acid
• Inositol nicotinate
• 5-Ethyl-2-(4-isopropyl-4-methyl-5-oxo-1H-imidazolin-2-yl)nicotinic acid
• Xanthinol nicotinate
• Nicotinic acid
• Methyl nicotinate
• Chromium picolinate
• Isonicotinic acid
• Zinc picolinate
• 2-Chloronicotinic acid
• N,N-Dimethylpropionamide
• 2,2-Dimethylbutyryl chloride
• 2-Phenylbutyric acid
• Difluorochloromethane
• Ethyl chloroformate
• 4,6-DICHLORO-8-METHYLQUINOLINE-3-CARBOXYLIC ETHYL ESTER
• ETHYL 4-CHLORO-8-FLUOROQUINOLINE-3-CARBOXYLATE