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2-(2-Hydroxyethyl)pyridine is a metabolite of the anti-vertigo drug Betahistine. It acts as a reagent for protection of the 5'-phosphate of nucleotides as 2-pyridylethyl (Pet) esters. It is used for carboxyl protection of amino acids. It is also used to cleave such groups as Boc and Fmoc, and also to hydrogenolysis. It was used to prepare mononuclear nickel(II) acetate.
Miha Trdin; Valter Bergant; Ivan Leban; Nina Lah. Two concomitant polymorphs of monomeric nickel acetate with 2-pyridineethanol. Acta Chimica Slovenica. 2012, 59, (3), 478-483.
Takashi Niwa; Hideki Yorimitsu; Koichiro Oshima. Palladium-Catalyzed 2-Pyridylmethyl Transfer from 2-(2-Pyridyl)ethanol Derivatives to Organic Halides by Chelation-Assisted Cleavage of Unstrained Cmath image[BOND]Cmath image Bonds. Angewandte Chemie (International Edition). 2007, 46, (15), 2643-2645.
Reagent for protection of the 5'-phosphate of nucleotides as 2-pyridylethyl (Pet) esters. The group can be introduced by DCC-coupling, is stable to mild base, but can be cleaved by methoxide in pyridine-methanol: Chem. Ber., 103, 1032 (1970).
Has also been used for carboxyl protection of amino acids. Pet esters are stable to both mildly acidic and basic conditions used to cleave such groups as Boc and Fmoc, and also to hydrogenolysis. Cleavage is by quaternization with methyl iodide in the presence of mild base: Tetrahedron Lett., 25, 3971 (1984); Angew. Chem. Int. Ed., 23, 716 (1984). See Appendix 6.
Hazard Statements: H227-H315-H319-H335
Combustible liquid. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P210-P235-P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P362-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep cool. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant