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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.
Hazard Statements: H226
Flammable liquid and vapour.
Precautionary Statements: P210-P280a-P240-P241-P303+P361+P353-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Dispose of contents/container in accordance with local/regional/national/international regulations.