| Identification | More | [Name]
6-Hydroxypicolinic acid | [CAS]
19621-92-2 | [Synonyms]
19621-92-22-PYRIDINECARBOXYLIC ACID, 1,6-DIHYDRO-6-OXO-
2-PYRIDINECARBOXYLIC ACID, 1,6-DIHYDRO-6-OXO
6-CARBOXY-2(1H)-PYRIDINONE
6-HYDROXY-2-PYRIDINECARBOXYLIC ACID
6-HYDROXYPICOLINIC ACID
6-HYDROXYPYRIDINE-2-CARBOXYLIC 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-HYDROXYPICOLINIC ACID 97+%
2-CARBOXY-1,6-DIHYDRO-6-OXOPYRIDINE
6-CARBOXY-2-HYDROXY-PYRIDINE
6-Hydroxypicolinic acid, 6-Hydroxypyridine-2-carboxylic acid | [EINECS(EC#)]
417-690-8 | [Molecular Formula]
C6H5NO3 | [MDL Number]
MFCD00192220 | [Molecular Weight]
139.11 | [MOL File]
19621-92-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Light yellow Cryst | [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 | [form ]
Powder | [pka]
3.29±0.20(Predicted) | [color ]
Yellow to brown | [BRN ]
115842 | [InChIKey]
VRCWSYYXUCKEED-UHFFFAOYSA-N | [CAS DataBase Reference]
19621-92-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow Cryst | [Uses]
6-Hydroxypyridine-2-carboxylic acid(19621-92-2) may be used in the preparation of ruthenium(II) complex, [RuH(CO)(6-OH-py-2-COO)(PPh3)2].
| [Definition]
ChEBI: 6-Hydroxypicolinic acid is an aromatic carboxylic acid and a member of pyridines. | [General Description]
6-Hydroxypyridine-2-carboxylic acid (6HPA, 6-Hydroxypicolinic acid,19621-92-2) 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.
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