19621-92-2

Basic information

• Product Name: 6-Hydroxypicolinic acid
• Synonyms: 2-PYRIDINECARBOXYLIC ACID, 1,6-DIHYDRO-6-OXO;19621-92-22-PYRIDINECARBOXYLIC ACID, 1,6-DIHYDRO-6-OXO-;6-CARBOXY-2(1H)-PYRIDINONE;6-HYDROXYPYRIDINE-2-CARBOXYLIC ACID;6-oxo-1,6-dihydropyridine-2-carboxylic acid;6-Hydroxypyridine-2-carboxylic acid 95%;6-HYDROXYPICOLINIC ACID;6-HYDROXY-2-PYRIDINECARBOXYLIC ACID
• CAS NO: 19621-92-2
• Molecular Formula: C₆H₅NO₃
• Molecular Weight: 139.11
• EINECS: 417-690-8
• Product Categories: Heterocyclic Building Blocks;blocks;Carboxes;Pyridines;pyridine derivative;Acids and Derivatives;Heterocycles;pharmacetical;Carboxylic Acids;Pyridine;Organic acids;Carboxylic Acids;Building Blocks;C6;Chemical Synthesis
• Mol File: 19621-92-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 270 °C (dec.)(lit.)
• Boiling Point: 436 °C at 760 mmHg
• Flash Point: 217.5 °C
• Appearance: Yellow to brown/Powder
• Density: 1.451 g/cm³
• Vapor Pressure: 8.03E-09mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 3.29±0.20(Predicted)
• BRN: 115842
• CAS DataBase Reference: 6-Hydroxypicolinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Hydroxypicolinic acid(19621-92-2)
• EPA Substance Registry System: 6-Hydroxypicolinic acid(19621-92-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 19621-92-2(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow Cryst

Uses

6-Hydroxypyridine-2-carboxylic acid may be used in the preparation of ruthenium(II) complex, [RuH(CO)(6-OH-py-2-COO)(PPh3)2].

General Description

6-Hydroxypyridine-2-carboxylic acid (6HPA, 6-Hydroxypicolinic acid) is a picolinic acid derivative. It has been reported to exhibit enol-keto tautomerism. It is a chelating ligand exhibiting potential complexing ability (via N,O-chelation or N,O,O-chelation). Intramolecular proton transfer (IPT) in tautomeric forms of 6HPA has been investigated by density functional theory (DFT) calculations.

InChI:InChI=1/C6H5NO3/c8-5-3-1-2-4(7-5)6(9)10/h1-3H,(H,7,8)(H,9,10)/p-1

Upstream product

• 672-67-3 2H-pyran-2-one-6-carboxylic acid 
• 98-98-6 2-Picolinic acid 
• 499-83-2 Pyridine-2,6-dicarboxylic acid 
• 27992-32-1 6-bromo-2-hydroxypyridine 
• 124-38-9 carbon dioxide 

Downstream Products

• 142-08-5 2-Pyridone 
• 30062-34-1 methyl 6-hydroxypyridine-2-carboxylate 
• 26256-72-4 6-methoxy-pyridine-2-carboxylic acid methyl ester 
• 89640-67-5 6-hydroxy-pyridine-2-carboxylic acid amide 
• 26893-73-2 6-methoxypyridine-2-carboxylic acid 
• 352514-21-7 6-(hydroxymethyl)pyridin-2 (1H)-one 
• 1006886-15-2 chloro(η6-biphenyl)(6-hydroxopicolinato)osmium(II) 
• 852669-68-2 C₂₀H₂₁N₅O₄ 
• 1254364-55-0 C₃₀H₃₇BN₄O₈ 
• 1412573-56-8 [RuH(CO)(6-OH-py-2-COO)(PPh₃)₂] 
• 1412573-56-8 [RuH(CO)(6-OH-py-2-COO)(PPh₃)₂] 
• 1420476-93-2 2-benzyl-3,4-dihydro-1H-pyrido[1,2-a]pyrazine-1,6(2H)-dione 
• 1420476-95-4 2-benzyl-3-methyl-3,4-dihydro-1H-pyrido[1,2-a]pyrazine-1,6(2H)-dione 
• 1420476-96-5 2-(1-phenylethyl)-3,4-dihydro-1H-pyrido[1,2-a]pyrazine-1,6(2H)-dione 

Related news

Supramolecular architectures from the self-assembly of lanthanide ions with 6-Hydroxypicolinic acid (cas 19621-92-2) and 1,10-phenanthroline08/30/2019

Three new lanthanide complexes, [La(HpicO)3(phen)(H2O)]n (1) and Ln3(picO)4(phen)3(H2O)2·HpicO·0.5H2O (Ln=Er (2), Yb (3)) were synthesized by the hydrothermal reactions and characterized by single crystal X-ray diffraction, elemental analysis and IR spectrum. In complex 1, each La(III) ion is ...detailed

Relevant articles and documents

Photochemistry of the three carboxypyridines in water: A pH dependent reaction

The photochemistry of ortho, meta and para-carboxypyridines (pK a1 = 1.0-2.1 and pKa1 = 4.7-5.3) in aqueous medium was studied by laser-flash photolysis and product studies. At pH a1, hydroxylated compounds are produced with low quantum yields. Within the pH range 4-7, ortho and meta isomers undergo dimerization together with decarboxylation with a quantum yield showing a very sharp maximum around pKa2 (φmax = 0.09 and 0.01, respectively) while the para isomer is photostable. End-of-pulse transients assigned to triplet states were detected by laser-flash photolysis at pH a1 and pH > 4. Additionally, the carboxypyridinyl radicals were detected as secondary intermediates at pH a1 and 4 a1. This is in favour of an electron transfer reaction between triplet and starting compound producing a charge transfer species. The radical anion would escape as carboxypyridinyl radical while the radical cation may add water at pH a1 yielding the OH-adduct radical or may undergo decarboxylation at pH > 4. The high quantum yield of phototransformation of the ortho isomer at pH > 4 is due to an easy decarboxylation process. A reaction scheme is proposed accounting for the dependences of φ on both the pH and the carboxypyridines concentration. This study points out the distinct pattern of reactivity of carboxypyridines depending on the ionisation state of starting compounds and isomeric substitution.

Infrared spectrum, molecular structure and theoretical calculation of 2-pyridone-6-carboxylic acid

The X-ray and infrared spectroscopic analysis of 2-pyridone-6-carboxylic acid are reported. The crystals of investigated molecule belong to P21/c of the monoclinic system, a = 11.714 ?, b = 3.7088?, c = 18.223? and β = 123.71°. The molecule is found in the ketonic form. Comprehensive studies of the molecular structures and vibrational frequencies and infrared intensities of the molecule have been performed by using Hartree-Fock, density functional B3LYP and second-order Moller-Plesset MP2 methods with the 6-31G+(d, p) basis set. The calculated geometrical parameters of investigated molecule in gas phase were compared with the experimental X-ray data.

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Preparation of 6-Oxo-1,6-dihydropyridine-2-carboxylic Acid by Microbial Hydroxylation of Pyridine-2-carboxylic acid

Alcaligenes faecalis (DSM 6269) grown on pyridine-2-carboxylic acid induced regiospecific hydroxylation of the latter to 6-oxo-1,6-dihydropyridine-2-carboxylic acid on a preparative scale.