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Home > Encyclopedia > 6-Hydroxypicolinic acid

6-Hydroxypicolinic acid

6-Hydroxypicolinic acid structure

6-Hydroxypicolinic acid 

structure
  • CAS No:

    19621-92-2

  • Formula:

    C6H5NO3

  • Chemical Name:

    6-Hydroxypicolinic acid

  • Synonyms:

    2-Pyridinecarboxylic acid,1,6-dihydro-6-oxo-;Picolinic acid,1,6-dihydro-6-oxo-;Picolinic acid,6-hydroxy-;1,6-Dihydro-6-oxo-2-pyridinecarboxylic acid;6-Hydroxypicolinic acid;6-Hydroxypyridine-2-carboxylic acid;2-Oxo-1,2-dihydropyridine-6-carboxylic acid;2-Hydroxypyridine-6-carboxylic acid;NSC 51589;6-Oxo-1,6-dihydropyridine-2-carboxylic acid;6-Hydroxy-2-picolinic acid;6-Oxopyridine-2-carboxylic acid;6-Oxo-1H-pyridine-2-carboxylicacid;19837-41-3

  • Categories:

    Pharmaceutical Intermediates  >  Heterocyclic Compound

Description

Light yellow Cryst


6-Hydroxypicolinic acid is an aromatic carboxylic acid and a member of pyridines.

6-Hydroxypicolinic acid Basic Attributes

139.11

139.11

417-690-8

51589

DTXSID10287567

29333990

Characteristics

66.4

-0.1

Yellow to brown Powder

1.451±0.06 g/cm3(Predicted)

282 °C (decomp)

436.0±45.0 °C(Predicted)

251.9±24.6 °C

1.626

8.03E-09mmHg at 25°C

Safety Information

IRRITANT

NONH for all modes of transport

3

36/37/38

26-36

Xi

P261-P305 + P351 + P338

H315-H319-H335

|Warning|H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

6-hydroxypicolinic acid

6-Hydroxypicolinic acid Use and Manufacturing

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.

Computed Properties

Molecular Weight:139.11
XLogP3:-0.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:139.026943022
Monoisotopic Mass:139.026943022
Topological Polar Surface Area:66.4
Heavy Atom Count:10
Complexity:239
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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