246159-22-8

Basic information

• Product Name: 4,4,4-trifluoro-3,3-dihydroxy-butyric acid
• Synonyms: 4,4,4-trifluoro-3,3-dihydroxy-butyric acid
• CAS NO: 246159-22-8
• Molecular Weight: 174.077
• Mol File: 246159-22-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4,4,4-trifluoro-3,3-dihydroxy-butyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4,4-trifluoro-3,3-dihydroxy-butyric acid(246159-22-8)
• EPA Substance Registry System: 4,4,4-trifluoro-3,3-dihydroxy-butyric acid(246159-22-8)

Safety Data

• Hazardous Substances Data: 246159-22-8(Hazardous Substances Data)

Upstream product

• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 400-36-2 trifluoroacetylacetic acid 

Downstream Products

• 86302-40-1 trifluoroacetoacetic acid enol 

Relevant articles and documents

Preparative synthesis of 2,2-dimethyl-5-(trifluoroacetyl)-1,3-dioxane-4,6-dione (2-trifluoroacetyl Meldrum's acid) and 2,2-dimethyl-6-(trifluoromethyl)-4H-1,3-dioxin-4-one and their synthetic usefulness as (trifluoroacetyl)ketene precursors

A simple and reliable method for the preparation of 2,2-dimethyl-5-(trifluoroacetyl)-1,3-dioxane-4,6-dione and 2,2-dimethyl-6-(trifluoromethyl)-4H-1,3-dioxin-4-one on a multigram scale was developed. These (trifluoroacetyl)ketene precursors were used in the hetero-Diels-Alder reaction with dialkylcyanamides and 1-ethoxyprop-1-yne, as well as in some reactions with nucleophiles.

The 4,4,4-trifluoroacetoacetic acid keto-enol system in aqueous solution. Generation of the enol by hydration of trifluoroacetylketene

Trifluoroacetylketene was generated in aqueous solution by flash photolysis of 2,2-dimethyl-6-trifluoromethyl-4H-1,3-dioxin-4-one and its spiro analogue, 4-trifluoromethyl-1,5-dioxaspiro[5.5]undec-3-en-2-one, and rates of hydration of the ketene to 4,4,4-trifluoroacetoacetic acid enol as well as subsequent ketonization of the enol were measured in this solvent across the acidity range [H+] = 10-1-10-12 M. Analysis of the rate profile produced by these data provides the acidity constants pQa,E = 1.85 for the carboxylic acid group of the enol and pQEa = 9.95 for its enolic hydroxyl group, which make these groups 2 and 3 orders of magnitude more acidic, respectively, than the corresponding groups in the parent unfluorinated acetoacetic acid enol. Rates of enolization of the keto group of 4,4,4-trifluoroacetoacetic acid were also measured, by bromine scavenging, and these, together with a value of the equilibrium constant for hydration of the keto group to its gem-diol derivative based upon a free energy relationship, Kh = 2900, provide an estimate of the keto-enol equilibrium constant for this system: pKE = 0.28. This is greater, by 2 orders of magnitude, than the keto-enol equilibrium constant for the unfluorinated acetoacetic acid.