Isonicotinic acid

Base Information

• Chemical Name: Isonicotinic acid
• CAS No.: 55-22-1
• Deprecated CAS: 1580002-27-2
• Molecular Formula: C6H5NO2
• Molecular Weight: 123.111
• Hs Code.: HYSICAL AND CHEMICAL PROPERTIES PHYSICAL STATE
• European Community (EC) Number: 200-228-2
• NSC Number: 1483
• UNII: Y8SYN761TQ
• DSSTox Substance ID: DTXSID8020757
• Nikkaji Number: J4.559D
• Wikipedia: Isonicotinic_acid
• Wikidata: Q410465
• Pharos Ligand ID: K8NP3Q7CVXWG
• Metabolomics Workbench ID: 49821
• ChEMBL ID: CHEMBL1203
• Mol file: 55-22-1.mol

Synonyms:Acid, Isonicotinic;Acids, Isonicotinic;Isonicotinic Acid;Isonicotinic Acids

Chemical Property of Isonicotinic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 5.56E-07mmHg at 25°C
• Melting Point: ≥300 °C(lit.)
• Refractive Index: 1.5423 (estimate)
• Boiling Point: 395.997 °C at 760 mmHg
• PKA: 4.96(at 25℃)
• Flash Point: 193.3 °C
• PSA: 50.19000
• Density: 1.293 g/cm³
• LogP: 0.77980
• Storage Temp.: -20°C
• Solubility.: 6g/l
• Water Solubility.: 5.2 g/L (20 ºC)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 123.032028402
• Heavy Atom Count: 9
• Complexity: 108

Purity/Quality:

98%min ^*data from raw suppliers

Isonicotinic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: C1=CN=CC=C1C(=O)O
• Recent ClinicalTrials: Isonicotinic Acid Hydrazide Pretreatment With Misoprostol Induction of Abortion in First-trimester Missed Miscarriage
• 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

Technology Process of Isonicotinic acid

There total 145 articles about Isonicotinic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

pyridine-4-carbaldehyde (872-85-5) → pyridine-4-carboxylic acid (55-22-1)

Guidance literature:

With formic acid; dihydrogen peroxide; at 0 - 4 ℃; for 12h; other aromatic aldehydes;

DOI:10.1055/s-1993-25851

Reference yield: 97.0%

picoline (108-89-4) → pyridine-4-carboxylic acid (55-22-1)

Guidance literature:

With sulfuric acid; ozone; acetic acid; manganese(II) acetate; at 16 ℃; for 1h;

Reference yield: 91.0%

pyridine-4-carbaldehyde (872-85-5) → pyridine-4-methanol (586-95-8) + pyridine-4-carboxylic acid (55-22-1)

Guidance literature:

With sodium hydroxide; In water; at 25 ℃; for 4h;

DOI:10.1039/c5nj02313k

upstream raw materials:

4-vinylpyridine

picoline

4-Ethylpyridine

2,4,6-trimethyl-pyridine

Downstream raw materials:

6-isonicotinoyl-2-phenyl-8H-pyrido[3,2-d][1,2]oxazin-5-one

4-pyridinecarboxylic acid, methyl ester

2,5-bis(4-pyridyl)-1,3,4-oxadiazole

isonicotinic acid 4-nitrophenyl ester

Refernces

• 1、 Lewis,Brown. "-". . p. 890,892. Retrieved 1944.
• 2、 Zhu, Xiao-Yan,Gong, Jin-Song,Li, Heng,Lu, Zhen-Ming,Shi, Jin-Song,Xu, Zheng-Hong. "Bench-scale biosynthesis of isonicotinic acid from 4-cyanopyridine by Pseudomonas putida". . p. 739 - 744. Retrieved 2014.
• 3、 Sultan, Sundas,Zulqarnain, Muhammad,Shah, Afzal,Firdous, Naveeda,Nisar, Jan,Ashiq, Muhammad Naeem,Bakhsh, Esraa M.,Khan, Sher Bahadar. "Bimetallic cobalt-iron diselenide nanorod modified glassy carbon electrode: an electrochemical sensing platform for the selective detection of isoniazid". . p. 12649 - 12657. Retrieved 2021.
• 4、 Funai,Blesa. "Kinetics and mechanism of the reaction of iodine with isonicotinoylhydrazide". . p. 2923 - 2928. Retrieved 1984.
• 5、 Afanas'eva et al.. "-". . . Retrieved 1968.
• 6、 Zhang, He,Yu, Kai,Lv, Jing-Hua,Wang, Chun-Mei,Wang, Chun-Xiao,Zhou, Bai-Bin. "Assembly of three organic-inorganic hybrid supramolecular materials based on reduced molybdenum(V) phosphates". . p. 22 - 30. Retrieved 2014.
• 7、 Ghobadi, Kobra,Zare, Hamid R.,Khoshro, Hossein,Gorji, Alireza. "Communication-electrosynthesis of isonicotinic acid via indirect electrochemical reduction of pyridine in the presence of CO2". . p. H240 - H242. Retrieved 2016.
• 8、 Shibamoto, Akihiro,Sakaguchi, Satoshi,Ishii, Yasutaka. "Aerobic oxidation of methylpyridines to pyridinecarboxylic acids catalyzed by N-hydroxyphthalimide". . p. 505 - 508. Retrieved 2000.
• 9、 Mehta, Praveen Kumar,Bhatia, Shashi Kant,Bhatia, Ravi Kant,Bhalla, Tek Chand. "Thermostable amidase catalyzed production of isonicotinic acid from isonicotinamide". . p. 1400 - 1404. Retrieved 2015.
• 10、 Khoshro, Hossein,Zare, Hamid R.,Jafari, Abbas A.,Gorji, Alireza. "Dual activity of electrocatalytic activated CO2 toward pyridine for synthesis of isonicotinic acid: An EC′C′C mechanism". . p. 69 - 71. Retrieved 2015.