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Hydroxyacetone is used as a reagent in organic chemical reactions. It also serves as a component for Mannich reaction and aldol reactions. It is also used in the syntheses of 2-oxo-propionaldehyde, imidazoles, polyols, acrolein, dyes and skin tanning agents. It yields (R)-1,2-propanediol upon reduction of hydroxyacetone in the presence of a microbial cell catalyst.
Acetol esters, formed by DCC coupling, have been employed as a means of carboxyl protection, stable to acid and hydrogenolysis, in peptide synthesis. They can be cleaved with TBAF in THF: Tetrahedron Lett., 33, 3193 (1992).
Albuquerque, E. M.; Borges, L. E.; Fraga, M. A. Lactic acid production from aqueous-phase selective oxidation of hydroxyacetone. J. Mol. Catal. A: Chem. 2015, 400, 64-70.
St Clair, J. M.; Spencer, K. M.; Beaver, M. R.; Crounse, J. D.; Paulot, F.; Wennberg, P. O. Quantification of hydroxyacetone and glycolaldehyde using chemical ionization mass spectrometry. Atmos. Chem. Phys. 2014, 14 (8), 4251-4262.
Gefahrenhinweise (EU): H226
Flammable liquid and vapour.
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