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142-08-5 - 2-Hydroxypyridine, 98% - 2-Pyridinol - 2(1H)-Pyridone - A14522 - Alfa Aesar

A14522 2-Hydroxypyridine, 98%

CAS Number
142-08-5
Synonyms
2-Pyridinol
2(1H)-Pyridone

Size Price ($) Quantity Availability
25g 37.39
100g 101.66
500g 326.40
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2-Hydroxypyridine, 98%

MDL
MFCD00006268
EINECS
205-520-3

Chemical Properties

Formula
C5H5NO
Formula Weight
95.10
Melting point
102-111°
Boiling Point
280-281°
Flash Point
210°(410°F)
Density
1.39
Solubility
Soluble in water 450 g/L @ 20°C and ethanol, slightly soluble in benzene and ether.

Applications

2-Hydroxypyridine is a bifunctional catalyst for a wide variety of acylation reactions, catalyst for generating β-oxopropyl carbonates from cyclic carbonates and alcohols and in the aminolysis of a polyglutamate. It is used in peptide synthesis.

Notes

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from strong oxidizing agents.

Literature References

Felix Plasser; Giovanni Granucci; Jiri Pittner; Mario Barbatti, Maurizio Persico; Hans Lischka. Surface hopping dynamics using a locally diabatic formalism: charge transfer in the ethylene dimer cation and excited state dynamics in the 2-pyridone dimer. Journal of Chemical Physics. 2012, 137 (22), 22A514.

Susan Blaser; Philipp Ottiger; Simon Lobsiger; Hans-Martin Frey; Samuel Leutwyler. Intermolecular clamping by hydrogen bonds: 2-pyridone⋅NH3. ChemPhysChem. 1999, 12 (10), 1841-1850.

Bifunctional catalyst for a wide variety of acylation reactions. See, for example: J. Chem. Soc. (C), 89 (1969).

For use of 2-pyridyl esters as active esters in peptide coupling, see: J. Chem. Soc.(C), 2896 (1971); Chem. Ber., 118, 468 (1985). The group can be introduced on to the N-protected peptide using DCC in pyridine, and is displaced by the amino-residue under mild conditions. For peptide reagents, see Appendix 6. Similar methodology has also been used in an improved preparation of trichloroethyl esters: Synthesis, 24 (1979).

Reacts with SOCl2 to form di-2-pyridyl sulfite, a useful reagent for in situ formation of N-sulfinylamines, nitriles, isocyanides and carbodiimides under mild conditions: Tetrahedron Lett., 27, 1925 (1986).

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H315-H319-H335

Toxic if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P301+P310-P305+P351+P338-P304+P340-P362-P312-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
105786
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2933.39
TSCA
Yes
RTECS
UV1144050

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