6-Chloronicotinic acid Chemical Properties

Melting point:

190 °C (dec.)(lit.)

Boiling point:

241.15°C (rough estimate)

Density 

0.5

refractive index 

1.5870 (estimate)

Flash point:

192°C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

deionized water: soluble

form 

Crystalline Powder

pka

3.24±0.10(Predicted)

color 

Off-white to beige

Water Solubility 

Soluble in water (2 mg/ml at 20°C), ethanol, methanol, DMSO, and slightly soluble in chloroform.

Decomposition 

192 ºC

BRN 

115993

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

UAWMVMPAYRWUFX-UHFFFAOYSA-N

CAS DataBase Reference

5326-23-8(CAS DataBase Reference)

NIST Chemistry Reference

6-Chloronicotinic acid(5326-23-8)

EPA Substance Registry System

6-Chloronicotinic acid (5326-23-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25-37/39

WGK Germany 

3

TSCA 

T

HazardClass 

IRRITANT

HS Code 

29333999

MSDS

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6-Chloronicotinic acid Usage And Synthesis

Chemical Properties

Off-white to beige crystalline powder

Uses

6-Chloronicotinic acid is used as building block for different chemical synthesis. It is an intermediate for the synthesis of N-(thiophen-2-yl) benzamide derivatives as BRAFV600E inhibitors, and novel DNA-gyrase B inhibitors.

Uses

6-Chloropyridine-3-carboxylic acid (6-chloronicotinic acid/6-CNA) has been used to study its photolytic and photocatalytic degradation. 6-CNA is a degradation product of neonicotinoid insecticides imidacloprid and acetamiprid and is known to appear in different environmental matrices. The product has been used as a media component during the isolation of 6-CNA degrading bacterial strain from imidacloprid-exposed soil samples.

Definition

ChEBI: 6-Chloronicotinic acid is a member of pyridines and an aromatic carboxylic acid.

General Description

6-Chloropyridine-3-carboxylic acid is a metabolite of the neonicotinoid pesticides, imidacloprid and acetamiprid and occurs in different environmental matrices.(3) It is widely used in agricultural crop protection, domestic insect control and environmental pest management.

Synthesis

In a 1000ml flask, add 450g chlorobenzene, 100g 2-chloro-5-methylpyridine, and 3g catalyst cobalt acetate under stirring, heat the system to 80℃, introduce oxygen, and control the oxygen flow rate at 0.4L/min. React under this condition for 4 hours. After the reaction, cool the system to room temperature, filter, and dry to obtain a mixture of 119g 6-chloronicotinic acid and cobalt acetate. Place those mentioned above mixed crude product in a 1000ml flask, add 600g of recrystallization solvent methanol, stir and heat to reflux; wait for the 6-chloronicotinic acid crude product to dissolve completely, keep warm for 5min, slowly cool the system to 5℃, precipitate a white product, maintain this internal temperature and continue stirring for 1 hour, filter, wash the filter cake once with a small amount of cooled methanol, and dry the obtained damp product at 80℃ for 4 hours to obtain 98.5g 6-chloronicotinic acid, purity 99.52% (HPLC), yield 79.7%.

Purification Methods

Purify it by recrystallisation from hot H2O and sublime it in a vacuum. [Pechmann & Welsch Chem Ber 17 2384 1884, Herz & Murty J Org Chem 26 122 1961, Beilstein 22/2 V 177.]

6-Chloronicotinic acid(5326-23-8)Related Product Information

• Isonicotinic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Xanthinol nicotinate
• Inositol nicotinate
• 2-Hydroxy-5-pyridinecarboxylic acid
• 2,6-Dichloro-5-fluoronicotinic acid
• 3,4,5-Trifluorobenzaldehyde
• 5,6-Dichloronicotinic acid
• 6-CHLORO-4-ETHOXYNICOTINIC ACID
• Ethyl 4,6-dichloronicotinate
• 2,6-Dichloronicotinic acid
• 6-Chloronicotinic acid methyl ester C7H6ClNO2,6-CHLORONICOTINIC ACID METHYL ESTER
• Difluorochloromethane
• 4,6-Dichloronicotinic acid
• 2-Amino-5-chloropyridine-3-carboxylic acid
• 5-BROMO-6-CHLORONICOTINIC ACID METHYL ESTER
• Ethyl 6-chloronicotinate
• METHYL 5,6-DICHLORONICOTINATE