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

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

Uses

Used in Chemical Synthesis:
4,4,4-TRIFLUORO-3-OXO-BUTYRIC ACID is used as a key intermediate in the synthesis of various complex organic molecules. Its unique structure, which includes the trifluoromethyl group, is often incorporated into pharmaceuticals, agrochemicals, and specialty chemicals to enhance their properties or reactivity.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4,4,4-TRIFLUORO-3-OXO-BUTYRIC ACID is used as a building block for the development of new drugs. Its presence in the molecular structure can impart specific biological activities or improve the pharmacokinetic properties of the final drug product, such as solubility, stability, or bioavailability.
Used in Material Science:
4,4,4-TRIFLUORO-3-OXO-BUTYRIC ACID is used as a component in the formulation of advanced materials, such as polymers and coatings, that require specific chemical or physical properties. The introduction of the trifluoromethyl group can enhance the thermal stability, chemical resistance, or other desirable characteristics of these materials.
Used in Analytical Chemistry:
4,4,4-TRIFLUORO-3-OXO-BUTYRIC ACID is employed as a reagent or derivatization agent in analytical chemistry for the detection and quantification of various compounds. Its unique chemical properties can facilitate the identification and separation of target analytes in complex samples.
Used in Industrial Processes:
4,4,4-TRIFLUORO-3-OXO-BUTYRIC ACID is utilized in various industrial processes, such as the production of specialty chemicals, agrochemicals, and intermediates for the synthesis of other compounds. Its versatility and reactivity make it a valuable asset in the chemical manufacturing sector.

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 
• 2261-53-2 4,4,4-trifluoro-3-oxobutanoyl chloride 
• 86302-40-1 trifluoroacetoacetic acid enol 

Downstream Products

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

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 TRIFLUOROACETYLACETIC ACID

The invention discloses a method for the preparation of trifluoroacetylacetic acid in its dehydrated form with a low content of the hydrate of trifluoroacetoacetic acid.

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.

Synthesis of low-fluoride organic compounds

Organic compounds, e.g. fluorinated organic compounds such as fluorinated carboxylic acids or fluorinated carboxylic acid chlorides, may contain small amounts of carboxylic acid fluorides, hydrogen fluoride or hydrolyzable fluoride, which during the preparation of derivatives of the fluorinated organic compounds, for example by esterification, may yield corrosive fluorides or hydrogen fluoride. The invention is a method for the synthesis and/or purification of preferably fluorinated organic compounds such as carboxylic acids, carboxylic acid chlorides and derivatives such as esters thereof, starting from corresponding carboxylic acid chlorides containing acid fluorides or hydrolyzable fluoride, and alcohols under the catalytic action of “onium” salts of carboxylic acids, to obtain products which have a low fluoride content. Alternatively, an inorganic oxide adsorbent is utilized. The method is especially suitable for the synthesis of esters of trifluoroacetic acid, chlorodifluoroacetic acid, trifluoroacetoacetic acid and/or difluoroacetoacetic acid.

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.