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HomeProduct name list6-Hydroxypicolinic acid

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
6-Hydroxypicolinic acid Structural

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.
6-Hydroxypicolinic acid synthesis

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)
ghs
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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