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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
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.
Solubility
Soluble in water 450 g/L @ 20°C and ethanol, slightly soluble in benzene and ether.
Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from strong oxidizing agents.
RUO – Research Use Only
General 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).