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6-Hydroxypicolinic acid

6-Hydroxypicolinic acid Structure
CAS No.
19621-92-2
Chemical Name:
6-Hydroxypicolinic acid
Synonyms
6-oxo-1,6-dihydropyridine-2-carboxylic acid;6-HYDROXYPICOLINIC ACID;6-CARBOXY-2(1H)-PYRIDINONE;6-hydroxy-2-pyridylic acid;6-HYDROXYPICOLINIC ACID 97+%;6-CARBOXY-2-HYDROXY-PYRIDINE;6-Hydroxypyridine-2-carboxyL;6-Hydroxy-2-pyridinecarboxylic;6-HPA, 6-hydroxypicolinic acid;6-oxo-1H-pyridine-2-carboxylicaci
CBNumber:
CB3712566
Molecular Formula:
C6H5NO3
Molecular Weight:
139.11
MOL File:
19621-92-2.mol
Modify Date:
2024/9/9 19:09:56

6-Hydroxypicolinic acid Properties

Melting point 270 °C (dec.) (lit.)
Boiling point 436.0±45.0 °C(Predicted)
Density 1.451±0.06 g/cm3(Predicted)
storage temp. Inert atmosphere,Room Temperature
pka 3.29±0.20(Predicted)
form Powder
color Yellow to brown
BRN 115842
InChIKey VRCWSYYXUCKEED-UHFFFAOYSA-N
CAS DataBase Reference 19621-92-2(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36
WGK Germany  3
HazardClass  IRRITANT
HS Code  29333990
NFPA 704
0
2 0

6-Hydroxypicolinic acid price More Price(4)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) 384305 6-Hydroxypyridine-2-carboxylic acid 95% 19621-92-2 5G ₹8995.58 2022-06-14 Buy
Sigma-Aldrich(India) 384305 6-Hydroxypyridine-2-carboxylic acid 95% 19621-92-2 25G ₹17807.13 2022-06-14 Buy
TCI Chemicals (India) H0876 6-Hydroxy-2-pyridinecarboxylic Acid 19621-92-2 5G ₹4500 2022-05-26 Buy
TCI Chemicals (India) H0876 6-Hydroxy-2-pyridinecarboxylic Acid 19621-92-2 25G ₹16800 2022-05-26 Buy
Product number Packaging Price Buy
384305 5G ₹8995.58 Buy
384305 25G ₹17807.13 Buy
H0876 5G ₹4500 Buy
H0876 25G ₹16800 Buy

6-Hydroxypicolinic acid Chemical Properties,Uses,Production

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.

Synthesis

6-Hydroxypicolinic acid is prepared by the reaction of 2-Bromo-6-hydroxypyridine and Carbon Dioxide. The specific synthesis steps are as follows:
To a solution of 2-bromo-6-hydroxypyridine (0.76 g, 4.4 mmol,1.0 equiv.) in dry THF (20 mL) at 0 C was added a 2 M solution of -PrMgCl in THF (2.2 mL,4.4 mmol, 1.0 equiv.) during 5 min. The clear solution was stirred at that temperature for anadditional 5 min, and a 2.5 M solution of n-BuLi in hexanes (3.5 mL, 8.8 mmol, 2.0 equiv.) wasadded dropwise during 5min, while maintaining the temperature below 20 C. The resultingmixture was stirred at that temperature for 0.5 h, dry CO2 (0.20 g, 1.0 equiv.) was added to20 C. The resulting mixture was warmed to 20 C in 0.5 h and quenched with water (6 mL).After stirring the mixture below 20 C for 10 min, the phases were separated and the water phasewas extracted one additional time with ethyl acetate. The resulting suspension was allowed to reachroom temperature and fitered through a mbox0.5 1 cm pad of silica gel eluted with 10 mL of ethylacetate. The ?ltrate was concentrated and the residue was puri?ed by ash chromatography on silicagel (eluent: petroleum ether/ethyl acetate = 10:1) to afford product 3m as off-white solid, 0.56 g (yield: 93percent) , m.p.: 275–277 C. 1H-NMR (600 MHz, DMSO) 7.56 (dd, J = 8.9, 7.0 Hz, 1H), 6.97 (d, J = 6.8 Hz,1H), 6.65 (d, J = 9.0 Hz, 1H). 13C-NMR (151 MHz, DMSO) 163.28, 162.67, 140.51, 137.97, 123.88, 110.42.
6-Hydroxypicolinic acid synthesis

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6-CARBOXY-2-HYDROXY-PYRIDINE 6-Hydroxypicolinic acid, 6-Hydroxypyridine-2-carboxylic acid 2-PYRIDINECARBOXYLIC ACID, 1,6-DIHYDRO-6-OXO 6-HYDROXYPICOLINIC ACID 97+% 2-CARBOXY-1,6-DIHYDRO-6-OXOPYRIDINE 6-Hydroxypyridine-2-carboxylic acid,6-Hydroxypicolinic acid, 6-Hydroxypyridine-2-carboxylic acid 6-Hydroxy-2-pyridinecarboxylic 6-oxo-1H-pyridine-2-carboxylic acid 6-HYDROXYPYRIDINE-2-CARBOXYLIC ACID 19621-92-22-PYRIDINECARBOXYLIC ACID, 1,6-DIHYDRO-6-OXO- 6-CARBOXY-2(1H)-PYRIDINONE 6-Hydroxypyridine-2-carboxylic acid 95% 6-HYDROXYPICOLINIC ACID 6-HYDROXY-2-PYRIDINECARBOXYLIC ACID 2-Hydroxy-6-PyridineCarboxylicAcid 6-Hydroxypyridine-2-Carboxylic Acid 6-Hydroxy-2-Pyridine Carboxylic Acid 2-Hydroxypyridine-6-carboxylic acid 2-PYRIDINE-6-HYDROXYCARBOXYLICACID 6-hydroxy-2-pyidine carboxylic acid 6-Hydroxypyridine-2-carboxylicacid:6-Hydroxypicolinic Acid 6-HPA, 6-hydroxypicolinic acid 6-Hydroxy-2-pyridinecarboxylicAcid> 6-Hydroxypyridine-2-carboxyL 6-oxo-1H-pyridine-2-carboxylicaci 6-hydroxy-2-pyridylic acid 6-Hydroxypicolinic acid ISO 9001:2015 REACH 6-oxo-1,6-dihydropyridine-2-carboxylic acid 19621-92-2 Building Blocks CARBOXYLIC ACID Heterocyclic Building Blocks Pyridines C6 Heterocyclic Building Blocks blocks Carboxes Pyridines pyridine derivative Acids and Derivatives Heterocycles Building Blocks C6 Chemical Synthesis Pyridine Organic acids pharmacetical Carboxylic Acids Carboxylic Acids