6-Hydroxypicolinic acid
Synonym(s):6-Hydroxypicolinic acid;6-Hydroxypyridine-2-carboxylic acid
- CAS NO.:19621-92-2
- Empirical Formula: C6H5NO3
- Molecular Weight: 139.11
- MDL number: MFCD00192220
- EINECS: 417-690-8
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-09-09 19:09:56
What is 6-Hydroxypicolinic acid?
Chemical properties
Light yellow Cryst
The Uses of 6-Hydroxypicolinic acid
6-Hydroxypyridine-2-carboxylic acid 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) 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.
Properties of 6-Hydroxypicolinic acid
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 |
CAS DataBase Reference | 19621-92-2(CAS DataBase Reference) |
Safety information for 6-Hydroxypicolinic acid
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 6-Hydroxypicolinic acid
InChIKey | VRCWSYYXUCKEED-UHFFFAOYSA-N |
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