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Home > Encyclopedia > 2-Chloro-5-hydroxypyridine

2-Chloro-5-hydroxypyridine

2-Chloro-5-hydroxypyridine structure

2-Chloro-5-hydroxypyridine 

structure
  • CAS No:

    41288-96-4

  • Formula:

    C5H4ClNO

  • Chemical Name:

    2-Chloro-5-hydroxypyridine

  • Synonyms:

    6-CHLOROPYRIDIN-3-OL;6-Chloro-3-pyridinol;3-PYRIDINOL, 6-CHLORO-;2-CHLORO-5-HYDROXYPYRIDINE;2-CHLORO-5-PYRIDINOL;2-Chloro-5-Pyridol;2-Chloropyridin-5-ol;3-Pyridinol,6-chloro-(9CI)

  • Categories:

    Pharmaceutical Intermediates  >  Heterocyclic Compound

Description

Light yellow Cryst

2-Chloro-5-hydroxypyridine Basic Attributes

129.54

128.998138

1533716-785-6

DTXSID50356120

2933399090

Characteristics

33.1

1.4

Light yellow cryst

1.4±0.1 g/cm3

155-158°C

351.9°C at 760 mmHg

166.6±22.3 °C

1.584

Safety Information

III

IRRITANT

36/37/38-22

26-36/37/39-36-37

T,Xi,Xn

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

H315

|Warning|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 10 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

2-chloro-5-hydroxypyridine

2-Chloro-5-hydroxypyridine Use and Manufacturing

2-Chloro-5-acetoxypyridine (21.66 g, 126 mmol) was dissolved in 300 mL of methanol and K2CO3(8.70 g, 63 mmol) was added. The reaction was stirred at room temperature for approx. 2 h, then concentrated in vacuo. The residue was diluted with diethyl ether and water, and the aqueous layer was adjusted to neutral pH by the addition of 1N aqueous HCl. Following extraction with diethyl ether, the organics were combined, washed with a solution of saturated aqueous NaCl, dried with MgSO4, and concentrated in vacuo. The resulting yellow solid (15.58 g, 96percent) was used without further purification.11b. 3) 2-Chloro-5-hydroxypyridine; Potassium carbonate (400 mg) was added to a solution of the 5-acetoxy-2-chloropyridine (10 g) in methanol (200 ml), and the mixture was stirred at room temperature for 20 hours. The reaction solvent was evaporated under reduced pressure, and the residue was purified by chromatography on silica gel (ethyl acetate) to give 2-chloro-5-hydroxypyridine (6.86 g, 91percent) as a solid. To a solution of acetic acid 6-chloro-pyridin-3-yl ester (1.67 g, 9.8 MMOL) in methanol (10 mL) was added potassium carbonate (676 mg, 4.9 MMOL), and the resulting reaction stirred at ambient temperature for 2 hours. The reaction was concentrated to an oily solid which was partitioned between water and diethyl ether. The water layer was neutralized with 3N HCI (3.7 mL), and extracted with diethyl ether (1X). The organics were combined, washed with brine, dried over sodium sulfate, and concentrated in vacuo to give the above named compound as a tan solid (1.04 g, 82percent).

Computed Properties

Molecular Weight:129.54
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:128.9981414
Monoisotopic Mass:128.9981414
Topological Polar Surface Area:33.1
Heavy Atom Count:8
Complexity:78.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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