Ethyl 4,4,4-trifluorocrotonate
Ethyl 4,4,4-trifluorocrotonate (CAS: 25597-16-4) is a valuable organic building block with the molecular formula C6H7F3O2 and a molecular weight of 168.11 g/mol. This ester, characterised by its trifluoromethyl group and alpha,beta-unsaturated carbonyl system, serves as a key intermediate in organic synthesis. It is frequently employed in the construction of complex molecules, particularly in the pharmaceutical and agrochemical sectors, due to the unique reactivity imparted by the fluorine atoms.
- IUPAC
- Ethyl 4,4,4-trifluoro-trans-2-butenoate
- Synonyms
- 25597-16-4CF3CH=CHCO2C2H5Ethyl 4,4,4-trifluoro-trans-2-butenoate
Synthesis of Pyroglutamic Acid Derivatives
Ethyl 4,4,4-trifluorocrotonate has been utilised in the synthesis of (2S,3S)-3-methyl- and (2S,3S)-3-trifluoromethylpyroglutamic acid. This application highlights its utility in creating chiral fluorinated heterocyclic compounds.
Diastereoselective Michael Additions
The compound readily undergoes diastereoselective Michael addition reactions with other unsaturated carbonyl compounds, such as ethyl crotonate. This reaction pathway is crucial for constructing carbon-carbon bonds stereoselectively.
Fluorinated Building Block
As a readily available source of a trifluoromethylated alkene, it serves as a versatile building block for introducing the CF3 moiety into organic molecules. This is important for modifying the properties of target compounds in medicinal chemistry.
| Molecular weight | 168.11 |
|---|---|
| Linear formula | CF3CH=CHCO2C2H5 |
| Assay | 98% |
| Boiling point | 114-115 °C(lit.) |
| Density | 1.125 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.3601(lit.) |
| Application | Ethyl 4,4,4-trifluorocrotonate was used in the synthesis of (2S,3S)-3-methyl- and (2S,3S)-3-trifluoromethylpyroglutamic acid. It undergoes diastereoselective Michael addition reaction with ethyl crotonate1. |
Hazard statements
- H226Flammable liquid and vapour
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P305IF IN EYES
| Protective equipment | Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
|---|---|
| Flash point | 26 °C / 78.8 °F |
| Transport (UN / ADR) | UN 3272 3 / PGIII |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xi |
| Risk statements (R) | 10-36/37 |
| Safety statements (S) | 16-26-27-28-36/37/39 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is Ethyl 4,4,4-trifluorocrotonate used for?
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Ethyl 4,4,4-trifluorocrotonate is primarily used as an intermediate and building block in organic synthesis. It has been employed in the synthesis of fluorinated pyroglutamic acid derivatives and undergoes diastereoselective Michael addition reactions.
What is the CAS number and formula for Ethyl 4,4,4-trifluorocrotonate?
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The CAS number is 25597-16-4, and its linear formula is CF3CH=CHCO2C2H5.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Ethyl 4,4,4-trifluorocrotonate with a purity of 98% (assay). This is a technical/research grade material, and TSS does not represent it as USP, BP, or EP grade.
How should Ethyl 4,4,4-trifluorocrotonate be handled safely?
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Ethyl 4,4,4-trifluorocrotonate is a flammable liquid and vapour (H226) and can cause serious eye irritation (H319) and respiratory irritation (H335). Handle with appropriate personal protective equipment, including eyeshields, face shields, and suitable gloves, in a well-ventilated area. Keep away from heat, hot surfaces, sparks, open flames, and other ignition sources.
Is Ethyl 4,4,4-trifluorocrotonate exported by Tech Serve Solutions?
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Yes, Tech Serve Solutions is a specialist global supplier and exporter of fine chemicals, including Ethyl 4,4,4-trifluorocrotonate.
How can I request a quote or sample?
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Please contact our sales team or use the online enquiry form on our website to request a quote or sample for Ethyl 4,4,4-trifluorocrotonate.
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