400-36-2

Basic information

• Product Name: 4,4,4-TRIFLUORO-3-OXO-BUTYRIC ACID
• Synonyms: 4,4,4-TRIFLUORO-3-OXO-BUTYRIC ACID;4,4,4-trifluoro-3-oxobutanoic acid
• CAS NO: 400-36-2
• Molecular Formula: C₄H₃F₃O₃
• Molecular Weight: 156.0600296
• Mol File: 400-36-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 189.633 °C at 760 mmHg
• Flash Point: 68.488 °C
• Appearance: /
• Density: 1.519
• Vapor Pressure: 0.25mmHg at 25°C
• Refractive Index: 1.359
• Storage Temp.: 2-8°C
• PKA: 0.83±0.32(Predicted)
• CAS DataBase Reference: 4,4,4-TRIFLUORO-3-OXO-BUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4,4-TRIFLUORO-3-OXO-BUTYRIC ACID(400-36-2)
• EPA Substance Registry System: 4,4,4-TRIFLUORO-3-OXO-BUTYRIC ACID(400-36-2)

Safety Data

• Hazardous Substances Data: 400-36-2(Hazardous Substances Data)

Usage

General Description

4,4,4-Trifluoro-3-oxo-butyric acid is a synthetic chemical compound characterized by its structure, which includes three fluorine atoms and a ketone functional group. Its molecular formula is C4H3F3O3 and it is also known by its systematic name, butanoic acid, 4,4,4-trifluoro-3-oxo-. 4,4,4-TRIFLUORO-3-OXO-BUTYRIC ACID belongs to the trifluorobutyric acids and derivatives class of compounds, and is used in a broad range of industrial and manufacturing applications due to its unique physical and chemical properties. However, like other chemical substances, appropriate precautions should be taken while handling or using it due to potential health hazards.

InChI:InChI=1/C4H3F3O3/c5-4(6,7)2(8)1-3(9)10/h1H2,(H,9,10)

Upstream product

• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 86302-40-1 trifluoroacetoacetic acid enol 
• 2261-53-2 4,4,4-trifluoro-3-oxobutanoyl chloride 

Downstream Products

• 340-71-6 2-oxo-4-phenyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester 
• 86302-40-1 trifluoroacetoacetic acid enol 
• 246159-22-8 4,4,4-trifluoro-3,3-dihydroxy-butyric acid 
• 421-50-1 1,1,1-trifluoro-2-propanone 
• 328956-11-2 7-Fluoro-6-methyl-4-trifluoromethyl-2(1H)-quinolinone 
• 1378854-54-6 C₄H₂F₃NO₃ 
• 1178533-14-6 3-phenyl-7-(trifluoromethyl)-3,4-dihydro-5H-imidazo[4,5-b]pyridin-5-one 
• 1178533-27-1 1-benzyl-7-(trifluoromethyl)-1H-imidazo[4,5-b]pyridin-5(4H)-one 
• 59938-06-6 4-ethoxy-1,1,1-trifluoro-3-butene-2-one 
• 205582-88-3 methyl 2-methyl-6-(trifluoromethyl)nicotinate 
• 917251-94-6 8-chloro-5-fluoro-2-(trifluoromethyl)quinolin-4-ol 
• 328956-13-4 6-methoxy-4-(trifluoromethyl)quinolin-2(1H)-one 
• 144765-05-9 6-trifluoromethyl-4-oxo-4H-1,3-dioxine-2-spirocyclohexane 
• 15719-64-9 methylammonium carbonate 

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.

METHOD FOR PREPARATION OF 4-ALKOXY-1,1,1-TRIFLUOROBUT-3-EN-2-ONES FROM TRIFLUOROACETYLACETIC ACID

The invention discloses a method for the preparation of 4-alkoxy and 4-aryloxy-1,1,1-trifluorobut-3-en-2-ones from trifluoroacetylacetic acid and orthoesters. Such compound can be used for the preparation of pharmaceutical, chemical or agro-chemical products.

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.