383-63-1

Basic information

• Product Name: Ethyl trifluoroacetate
• Synonyms: aceticacid,trifluoro-,ethylester;CF3COOC2H5;Ethyl ester of Trifluoroacetic acid;Ethyl trifluoroethanoate;ethylperfluoroacetate;Trifluoressigsαureethylester;trifluoro-aceticaciethylester;ETHYL 2,2,2-TRIFLUOROACETATE
• CAS NO: 383-63-1
• Molecular Formula: C₄H₅F₃O₂
• Molecular Weight: 142.08
• EINECS: 206-851-6
• Product Categories: Fluoro-Aliphatics ;Acetics acid and esters;Organic Fluorides;Fluorinated Building Blocks;Fluorinating Reagents & Building Blocks for Fluorinated Biochemical Compounds;Synthetic Organic Chemistry;organofluorine compounds;Building Blocks;C2 to C5;Carbonyl Compounds;Chemical Synthesis;Esters;Organic Building Blocks;Pharmaceutical intermediates
• Mol File: 383-63-1.mol
• Article Data: 56

Chemical Properties

• Melting Point: -78 °C
• Boiling Point: 60-62 °C(lit.)
• Flash Point: 30 °F
• Appearance: Clear/Liquid
• Density: 1.194 g/mL at 25 °C(lit.)
• Vapor Pressure: 56mmHg at 25°C
• Refractive Index: n20/D 1.307(lit.)
• Storage Temp.: 2-8°C
• Solubility: 4g/l
• PKA: 0.43[at 20 ℃]
• Water Solubility: HYDROLYSIS
• Sensitive: Moisture Sensitive
• BRN: 1761411
• CAS DataBase Reference: Ethyl trifluoroacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl trifluoroacetate(383-63-1)
• EPA Substance Registry System: Ethyl trifluoroacetate(383-63-1)

Safety Data

• Hazard Codes: F,Xn,C
• Statements: 11-22-37/38-41-34
• Safety Statements: 9-16-26-36/39-45-36/37/39
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 1
• TSCA: T
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 383-63-1(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to yellow liquid

Uses

Different sources of media describe the Uses of 383-63-1 differently. You can refer to the following data:
1. Ethyl Trifluoroacetate is an intermediate used in the synthesis of various pharmaceutically active molecules and agricultural products. Ethyl Trifluoroacetate is also useful for the preparation of tri fluoroacylated compounds.
2. Ethyl trifluoroacetate is used as an intermediate in organic synthesis to prepare organic fluorine compounds like 3-ethyl-1-methylimidazolium trifluoroacetate (EMITA). It is involved in the syntheses of various pharmaceutically active molecules and agricultural products. It is also useful for the preparation of tri fluoroacylated compounds.

Flammability and Explosibility

Highlyflammable

Purification Methods

Fractionate it through a long Vigreux column (p 11). IR has max at 1800 (CO2) and 1000 (OCO) cm-1 [Fuson et al. J Chem Phys 20 1627 1952, Bergman J Org Chem 23 476 1958]. [Beilstein 2 IV 463.]

InChI:InChI=1/C4H5F3OS/c1-2-9-3(8)4(5,6)7/h2H2,1H3

Upstream product

• 866-23-9 diethyl (trichloromethyl)phosphonate 
• 76-05-1 trifluoroacetic acid 
• 74-84-0 ethane 
• 407-25-0 trifluoroacetic anhydride 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 368-66-1 2,4,6-tris(trifluoromethyl)-1,3,5-triazine 
• 7732-18-5 water 
• 129880-37-1 Sodium; 2-ethoxy-2,3,3,3-tetrafluoro-propionate 
• 433-28-3 trifluoro-acetic acid vinyl ester 
• 19629-18-6 diethylethoxystibine 
• 93749-47-4 methyl 4-(2,2-diethoxyethoxy)benzoate 
• 1569262-64-1 ethyl N-tert-butyl-4-nitrobenzenesulfonimidate 
• 354-32-5 trifluoracetyl chloride 

Downstream Products

• 581-83-9 1-([1,1'-biphenyl]-4-yl)-4,4,4-trifluorobutane-1,3-dione 
• 315-09-3 4,4,4-trifluoro-1-(2-hydroxy-4,6-dimethyl-phenyl)-butane-1,3-dione 
• 578-30-3 1-(2,5-dimethyl-[3]thienyl)-4,4,4-trifluoro-butane-1,3-dione 
• 507-52-8 2-(trifluoromethyl)-2-propanol 
• 421-50-1 1,1,1-trifluoro-2-propanone 
• 374-01-6 1,1,1-trifluoroisopropanol 
• 541-80-0 1,1,1-trifluoro-6-methyl-hept-5-ene-2,4-dione 
• 319-25-5 4,4,4-trifluoro-1-(2-hydroxy-5-methyl-phenyl)-butane-1,3-dione 
• 387-89-3 2-(2,2,2-trifluoroacetyl)cyclohexanone 
• 582-65-0 1-(4-fluorophenyl)-4,4,4-trifluoro-1,3-butanedione 
• 361-73-9 2-(trifluoroacetyl)cyclopentanone 
• 326-06-7 1-Phenyl-4,4,4-trifluorobutane-1,3-dione 
• 318-46-7 2-(2,2,2-trifluoroacetyl)-3,4-dihydro-2H-naphthalen-1-one 
• 367-57-7 1,1,1-Trifluoro-2,4-pentanedione 

Relevant articles and documents

Stable carbocations XXIII. Generation and isolation of salts of ferrocenyl(alkoxy)methylium cations and their intermediacy in acid-promoted acetal hydrolysis

Ferrocenyl(aloxy)methylium cations have been generated from (dialkoxymethyl)ferrocenes and isolated as tetrafluoroborate salts.Their structures and their reactivity towards nucleophiles have been investigated.

A facial chemoenzymatic method for the preparation of chiral 1,2-dihydroxy-3,3,3,-trifluoropropanephosphonates

A convenient and effective method for the preparation of chiral trifluoromethylated 1,2-dihydroxypropanephosphonates based on a chemoenzymatic approach was described. Ethyl trifluoromethylacetate was reacted with anion of methylphosphonate to give 2-oxo-3,3,3-trifluoropropanephosphonate and its hydrates, 2,2-dihydroxy-3,3,3-trifluoropropanephosphonates, which are reduced with sodium boronhydride affording 2-hydroxy-3,3,3-trifluoropropanephosphonates. The product thus obtained was then transferred to corresponding 1,2-vinyl-3,3,3-trifluoropropanephosphonate and followed by 1,2-dihydroxylation via potassium permanganate treatment. Enzymatic kinetic resolution of the resultant racemate by CALB or IM provided optically active 1,2-dihydroxy-3,3,3- trifluoropropanephosphonate with satisfactory chemical and enantiomeric yield.

Aerobic Partial Oxidation of Alkanes Using Photodriven Iron Catalysis

Photodriven oxidations of alkanes in trifluoroacetic acid using commercial and synthesized Fe(III) sources as catalyst precursors and dioxygen (O2) as the terminal oxidant are reported. The reactions produce alkyl esters and occur at ambient temperature in the presence of air, and catalytic turnover is observed for the oxidation of methane in a pure O2 atmosphere. Under optimized conditions, approximately 17% conversion of methane to methyl trifluoroacetate at more than 50% selectivity is observed. It is demonstrated that methyl trifluoroacetate is stable under catalytic conditions, and thus overoxidized products are not formed through secondary oxidation of methyl trifluoroacetate.

Low-Flammable Parahydrogen-Polarized MRI Contrast Agents

Many MRI contrast agents formed with the parahydrogen-induced polarization (PHIP) technique exhibit biocompatible profiles. In the context of respiratory imaging with inhalable molecular contrast agents, the development of nonflammable contrast agents would nonetheless be highly beneficial for the biomedical translation of this sensitive, high-throughput and affordable hyperpolarization technique. To this end, we assess the hydrogenation kinetics, the polarization levels and the lifetimes of PHIP hyperpolarized products (acids, ethers and esters) at various degrees of fluorine substitution. The results highlight important trends as a function of molecular structure that are instrumental for the design of new, safe contrast agents for in vivo imaging applications of the PHIP technique, with an emphasis on the highly volatile group of ethers used as inhalable anesthetics.