Isonicotinic acid Property

Melting point:

≥300 °C (lit.)

Boiling point:

260 °C (15 mmHg)

Density 

1,47g/cm

refractive index 

1.5423 (estimate)

Flash point:

260°C/15mm

storage temp. 

no restrictions.

solubility 

6g/l

pka

4.96(at 25℃)

form 

powder

color 

yellow to tan

PH

3-4 (6g/l, H2O, 20℃)(saturated solution)

Water Solubility 

5.2 g/L (20 ºC)

Merck 

14,5187

BRN 

109599

InChIKey

TWBYWOBDOCUKOW-UHFFFAOYSA-N

CAS DataBase Reference

55-22-1(CAS DataBase Reference)

NIST Chemistry Reference

Isonicotinic acid(55-22-1)

EPA Substance Registry System

Isonicotinic acid (55-22-1)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

2

RTECS 

NS1103000

TSCA 

Yes

HS Code 

29333999

Toxicity

LD50 orally in Rabbit: 5000 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

Isonicotinic acid Chemical Properties,Usage,Production

Chemical Properties

isonicotinic acid is also known as pyridine-4-carboxylic acid. white to light yellow crystal powder or white needle crystals. odorless, sublimable. molecular weight 123.11. melting point 319°C . slightly soluble in cold water, soluble in hot water, insoluble in alcohol, benzene and ether. isonicotinic acid is an amphoteric compound that is soluble in both acids and bases. soluble in hot water and ethanol, slightly soluble in cold water and ether. stable to heat and oxidation.

Uses

Isonicotinic acid is a metabolite of isoniazid. It is an isomer of nicotinic acid. The chronic toxicity of isonicotinic acid is slightly higher than that of isonicotinic acid hydrazide ( INH ) .
Isonicotinic acid is a moderately basic compound (based on its pKa). Isonicotinic acid is an organic compound with a carboxyl group on a pyridine ring. The carboxyl group for isonicotinic acid is on the 4-position instead of the 3-position for nicotinic acid. It is an isomer of nicotinic acid. Isonicotinic acid is a metabolite of isoniazid.
Isonicotinic acid considered to be inactive isomer of nicotinic acid. Isonicotinic acid is a metabolite of pyridine-4-carboxy hydrazide (isonicotinyl hydrazide; isoniazid) a front-line weapon in the battle against tuberculosis. Isonicotinic acid and its derivatives are used in manufacturing pharmaceuticals and agrochemicals.
Used in the biological study of differentiation induced by nicotinic acid, nicotinamide and isonicotinic acid in human leukemia cell lines

Definition

ChEBI: Isonicotinic acid is a pyridinemonocarboxylic acid in which the carboxy group is at position 4 of the pyridine ring. It has a role as a human metabolite and an algal metabolite. It is a conjugate acid of an isonicotinate.

Preparation

Isonicotinic acid is synthesized by continuous oxidation with 4-methylpyridine as raw material and vanadium pentoxide as catalyst. The purity of the industrial product isonicotinic acid is more than 95%, and the yield of the above method is 70-75%. The consumption of 4-methylpyridine per ton of product is 1070kg.

Application

Isonicotinic acid (IN) can be used as:
An organocatalyst in the one pot four component condensation reaction, to synthesize pyranopyrazoles based heterocyclic compounds.
An organic ligand for the preparation of copper(I) halide coordination polymer [CuBr(IN)]n, by hydrothermal method.
As a starting material for the synthesis of cation-dimers with potent antimalarial activity.

Purification Methods

Crystallise the acid repeatedly from water and dry it under vacuum at 110o or sublime it at 260o/15mm (m 319o). [Beilstein 22 III/IV 518, 22/2 V 188.]