Isonicotinic acid

Isonicotinic acid Basic information
Product Name:Isonicotinic acid
Synonyms:4-PYRIDINECARBOXYLIC ACID FOR SYNTHESIS;Isonicotinic aci;66 kDa neurofilament protein;ANTI-INA (ALPHA INTERNEXIN) (CENTER) antibody produced in rabbit;NEF5;Neurofilament 5;Pyridine-4-carboxylic acid, 4-Carboxypyridine;Isonicotinic acid, CP,98%
CAS:55-22-1
MF:C6H5NO2
MW:123.11
EINECS:200-228-2
Product Categories:Building Blocks;C6;Nitrogen cyclic compounds;API’s;Chemical Synthesis;Heterocyclic Building Blocks;Pyridine;API intermediates;Heterocycles;Pyridines;carboxylic acid;bc0001;55-22-1
Mol File:55-22-1.mol
Isonicotinic acid Structure
Isonicotinic acid Chemical Properties
Melting point ≥300 °C (lit.)
Boiling point 260 °C (15 mmHg)
density 1,47g/cm
refractive index 1.5423 (estimate)
Fp 260°C/15mm
storage temp. no restrictions.
solubility 6g/l
pka4.96(at 25℃)
form powder
color yellow to tan
PH3-4 (6g/l, H2O, 20℃)(saturated solution)
Water Solubility 5.2 g/L (20 ºC)
Merck 14,5187
BRN 109599
InChIKeyTWBYWOBDOCUKOW-UHFFFAOYSA-N
CAS DataBase Reference55-22-1(CAS DataBase Reference)
NIST Chemistry ReferenceIsonicotinic acid(55-22-1)
EPA Substance Registry SystemIsonicotinic acid (55-22-1)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 2
RTECS NS1103000
TSCA Yes
HS Code 29333999
ToxicityLD50 orally in Rabbit: 5000 mg/kg
MSDS Information
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Isonicotinic acidEnglish
ACROSEnglish
SigmaAldrichEnglish
ALFAEnglish
Isonicotinic acid Usage And Synthesis
Chemical Propertiesisonicotinic 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.
UsesIsonicotinic 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
DefinitionChEBI: 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.
PreparationIsonicotinic 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.
ApplicationIsonicotinic 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 MethodsCrystallise 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.]
Isonicotinic acid Preparation Products And Raw materials
Raw materialsVanadium(V) oxide
Preparation Products2-Chloro-4-pyridinecarboxylic acid–>Forchlorfenuron–>4-Amino-2-chloropyridine–>4-ISOCYANATOPYRIDINE–>ISONICOTINOYL CHLORIDE HYDROCHLORIDE–>2-IODO-ISONICOTINIC ACID–>3-BROMO-N-PHENYLPYRIDINE-4-CARBOXAMIDE–>2-SULFANYLISONICOTINIC ACID–>2,5-BIS(4-PYRIDYL)-1,3,4-THIADIAZOLE–>3-Bromoisonicotinic acid–>2-Chloropyridine-4-carbonyl chloride–>4-(Ethylaminomethyl)pyridine–>N-PHENYLISONICOTINAMIDE–>Isoniazid–>4-Pyridylcarbinol–>Isonicotinic acid chloride–>3,4-Pyridinedicarboxylic acid–>Ethyl isonicotinate

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