3-Hydroxypicolinic acid

Base Information

• Chemical Name: 3-Hydroxypicolinic acid
• CAS No.: 874-24-8
• Molecular Formula: C6H5NO3
• Molecular Weight: 139.111
• Hs Code.: 29333990
• European Community (EC) Number: 212-859-0
• UNII: XV7XP64JR5
• DSSTox Substance ID: DTXSID80236320
• Nikkaji Number: J195.156D
• Wikipedia: 3-Hydroxypicolinic_acid
• Wikidata: Q10859486
• Metabolomics Workbench ID: 42237
• ChEMBL ID: CHEMBL1234326
• Mol file: 874-24-8.mol

Synonyms:3-hydroxy-2-pyridinecarboxylic acid;3-hydroxypicolinic acid

Chemical Property of 3-Hydroxypicolinic acid

Chemical Property:

• Appearance/Colour: Light yellow needles
• Vapor Pressure: 6.34E-09mmHg at 25°C
• Melting Point: 208-212 °C
• Refractive Index: 1.5423 (estimate)
• Boiling Point: 451.1 °C at 760 mmHg
• PKA: 1.14±0.50(Predicted)
• Flash Point: 226.6 °C
• PSA: 70.42000
• Density: 1.485 g/cm³
• LogP: 0.48540
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Acetonitrile (Slightly), DMSO (Slightly)
• Water Solubility.: Soluble in water (0.25g in 10ml).
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 139.026943022
• Heavy Atom Count: 10
• Complexity: 137

Purity/Quality:

99% ^*data from raw suppliers

3-Hydroxypicolinic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/22
• Safety Statements: 26-28-36/37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(N=C1)C(=O)O)O
• Uses: 3-Hydroxypicolinic acid (3-HPA) is a matrix material used in matrix-assisted laser desorption/ionization (MALDI) based mass spectroscopy (MS) for the analysis of large biomolecules and quantification of oligonucleotides.

Technology Process of 3-Hydroxypicolinic acid

There total 15 articles about 3-Hydroxypicolinic 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: 32.0%

3-amino-2-picolinehydroxamic acid (98140-94-4) → 3-hydroxypyridine-2-carboxylic acid (874-24-8) + 3-hydroxy-4-oxo-3,4-dihydro-5-azabenzo-1,2,3-triazine (655244-89-6)

Guidance literature:

With hydrogenchloride; sodium nitrite; In water; at 5 ℃; for 0.5h;

DOI:10.1021/jo030017a

Reference yield:

3-hydroxypyridine-2-carbonitrile (932-35-4) → 3-hydroxypyridine-2-carboxylic acid (874-24-8)

Guidance literature:

With water; sodium hydroxide; In ethanol; for 12h; Reflux;

Reference yield:

→ 3-hydroxypyridine-2-carboxylic acid (874-24-8)

Guidance literature:

With carbon dioxide; at 215 - 220 ℃; under 33097.9 Torr;

upstream raw materials:

2-Formyl-3-hydroxypyridin

2-Picolinic acid

3-amino-2-picolinehydroxamic acid

(S)-4,5-dihydro-2-(3-hydroxy-2-pyridinyl)-4-methyl-4-thiazolecarboxylic acid

Downstream raw materials:

2,6-diiodo-3-hydroxypyridine

3-benzyloxypyridine-2-carboxylic acid

3-benzyloxypyridine-2-carbonyl chloride

cis-[Pt(PPh₃)2Cl(picOH)]*CHCl₃

Refernces

• 1、 -. "Method for synthesizing 3-hydroxy-2-picolinic acid and derivatives thereof". . . Retrieved 2020/12/31.
• 2、 Suante,Mahanti. "Kinetic studies on the quinolinium dichromate oxidation of heteroacids". . p. 1813 - 1819. Retrieved 2007/10/03.