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Chemical structure of Ethyl Fluoroacetate | 459-72-3
CAS: 459-72-3
SKU: S1528
Ethyl Fluoroacetate | SKU: S1528
Synonyms: Ethyl 2-fluoroacetate; Ethyl monofluoroacetate; Fluoroacetic acid ethyl ester; Monofluoroacetic acid ethyl ester
Chemical structure of Ethyl Fluoroacetate | 459-72-3
Ethyl fluoroacetate (ethyl 2-fluoroacetate, FCH2COOC2H5) is the ethyl ester of fluoroacetic acid, a small, volatile organofluorine ester with a molecular weight of 106.10 g/mol. It is a clear liquid that boils at about 119 °C, has a density of 1.098 g/mL at 25 °C and a refractive index of n20/D 1.375, dissolves in water and has a closed-cup flash point of 31 °C, so it is classed as a flammable liquid. The reference assay is 98%. The fluorine atom next to the carbonyl makes the molecule a compact source of an α-fluoroacetyl unit. The α-CH2 is acidic enough for enolate chemistry, while the C–F bond survives most reaction conditions, which is why the ester is used to build fluorinated side chains and intermediates. It is the starting reagent for ethyl (diethoxyphosphoryl)fluoroacetate, the phosphonate used in Horner–Wadsworth–Emmons olefinations to make α-fluoro-α,β-unsaturated esters, it has been used in the synthesis of 4-deoxy-4-fluoro-muscarines, and it has been applied in the development of an ammonolysis-based microencapsulation process. Ethyl fluoroacetate is acutely toxic by ingestion, skin contact and inhalation, as are other fluoroacetate derivatives, so it is intended for trained personnel working with proper engineering controls. Sarchem Labs provides ethyl fluoroacetate (SKU S1528) for industrial and research customers that can meet those requirements, with a Certificate of Analysis and Safety Data Sheet for each lot; laboratory to bulk quantities can be quoted on request.
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Specifications

Boiling Point119.3°C at 753 mmHg (lit.)
Density1.098 g/mL at 25°C (lit.)
Flash Point31°C (87.8°F), closed cup
ColorYellow
Linear FormulaFCH2COOC2H5
Formula Weight106.10
Physical FormClear Liquid at 20°C
Chemical Name or MaterialEthyl fluoroacetate
UN Number2929
SMILES StringCCOC(=O)CF
Refractive Indexn20/D 1.375 (lit.)
Assay98%
SolubilitySoluble in water
CAS Number459-72-3
EC Number207-297-8
NACRESNA.22
PubChem Substance ID24850037
UNSPSC Code12352100
MDL NumberMFCD00000450
InChI1S/C4H7FO2/c1-2-7-4(6)3-5/h2-3H2,1H3
InChI KeyVCYZVXRKYPKDQB-UHFFFAOYSA-N
PubChem CID9988
Beilstein/REAXYS Number1743761
Quality Level100
Functional GroupsEster, fluoro
FormLiquid (clear liquid at 20°C)

Applications

No Application Found
Fluorinated bioactive analogues: used in the synthesis of 4-deoxy-4-fluoro-muscarines, fluorinated analogues of the muscarinic agonist muscarine for receptor studies.
Claisen and aldol building block: the α-fluoro ester enolate can be condensed with esters and carbonyl compounds to give α-fluoro-β-keto and β-hydroxy esters; addition to formaldehyde followed by dehydration is a documented, if demanding, route to alkyl 2-fluoroacrylate monomers.
Microencapsulation process development: applied in the development of an ammonolysis-based microencapsulation process.
Fluoro-organic intermediate research: a low-molecular-weight C2 source of the α-fluoroacetyl unit for fluorinated side chains in pharmaceutical and agrochemical R&D.

Product Description

What is Ethyl Fluoroacetate?

Ethyl fluoroacetate is the ester of fluoroacetic acid and ethanol, C4H7FO2, with a molecular weight of 106.10 g/mol. Compared with ethyl acetate, the electronegative fluorine makes the carbonyl carbon more electrophilic and the α-CH2 more acidic, while the carbon–fluorine bond itself is strong and chemically inert in most synthetic sequences. It is a liquid (boiling point 119.3 °C at 753 mmHg, density 1.098 g/mL at 25 °C) that is soluble in water.

Like other fluoroacetate derivatives, the compound is highly toxic to humans and animals, which is the dominant consideration when it is purchased, stored and used. It should not be confused with ethyl difluoroacetate or ethyl trifluoroacetate, which are different, less acutely toxic reagents with their own CAS numbers.

Uses of Ethyl Fluoroacetate

In synthesis, ethyl fluoroacetate is mainly a route to fluorinated building blocks. Conversion to ethyl (diethoxyphosphoryl)fluoroacetate gives a Horner–Wadsworth–Emmons reagent for α-fluoroacrylates, which are valued as rigid, metabolically robust motifs in drug candidates; direct enolate chemistry delivers α-fluoro-β-keto esters and related intermediates; and the ester has been used to make fluorinated muscarine analogues for pharmacology.

Beyond fine-chemical synthesis, it has been applied in the development of an ammonolysis-based microencapsulation process, and its enolate addition to formaldehyde, followed by dehydration, has been reported as a route to alkyl 2-fluoroacrylate monomers.

Buying and Handling Considerations

Confirm that your site can store and handle acutely toxic, flammable liquids before ordering. Use a fume hood or closed system, chemical-resistant gloves, eye and face protection and an ABEK-type respirator filter where exposure is possible, and keep spill-control and emergency procedures in place. Store the liquid locked up, tightly closed, in a cool, well-ventilated flammables area away from ignition sources, bases and oxidisers. Transport follows UN 2929 (toxic liquid, flammable, organic, n.o.s.). Ask for the assay (GC) on the Certificate of Analysis.

Safety Information

  • Pictograms / Signal Word: GHS02 (flame), GHS06 (skull and crossbones), GHS05 (corrosion), GHS09 (environment) | Danger
  • Hazard Statements: H226 (flammable liquid and vapour), H300 (fatal if swallowed), H311 + H331 (toxic in contact with skin or if inhaled), H318 (causes serious eye damage), H400 (very toxic to aquatic life)
  • Hazard Classification: Acute Tox. 2 Oral, Acute Tox. 3 Dermal, Acute Tox. 3 Inhalation, Aquatic Acute 1, Eye Dam. 1, Flam. Liq. 3
  • Precautionary Statements: P210, P273, P280, P301 + P310, P303 + P361 + P353, P305 + P351 + P338
  • Storage Class: 3 – Flammable liquids | WGK: 3 | Flash Point: 31°C (87.8°F), closed cup
  • Transport: UN 2929 (toxic liquid, flammable, organic, n.o.s.)
  • PPE: Eyeshields, faceshields, gloves, type ABEK (EN14387) respirator filter

Fatal if swallowed and toxic by skin contact and inhalation: never handle outside a fume hood or closed system, avoid all release to drains and the environment, and obtain medical attention immediately after any exposure.

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FAQs: Ethyl Fluoroacetate

It is used as a fluorinated building block: the starting reagent for the Horner–Wadsworth–Emmons phosphonate ethyl (diethoxyphosphoryl)fluoroacetate, in the synthesis of fluorinated muscarine analogues, in Claisen and aldol chemistry that delivers α-fluoro esters, and in the development of a microencapsulation process.

Yes. Ethyl fluoroacetate, ethyl 2-fluoroacetate, ethyl monofluoroacetate and fluoroacetic acid ethyl ester are the same compound, CAS 459-72-3, formula C4H7FO2. It differs from ethyl difluoroacetate and ethyl trifluoroacetate.

Molecular weight 106.10 g/mol, boiling point 119.3 °C at 753 mmHg, density 1.098 g/mL at 25 °C, refractive index n20/D 1.375 and a closed-cup flash point of 31 °C. It is a liquid that dissolves in water.

It is acutely toxic: fatal if swallowed (H300) and toxic in contact with skin or if inhaled (H311 + H331). It is also a flammable liquid and causes serious eye damage. Only trained personnel should use it, in a fume hood or closed system.

Store it locked up, tightly closed, in a cool and well-ventilated flammables area away from heat, bases and oxidisers. It ships as UN 2929, toxic liquid, flammable, organic, n.o.s.

No. It is the starting reagent for the phosphonate ethyl (diethoxyphosphoryl)fluoroacetate, and that phosphonate is the Horner–Wadsworth–Emmons reagent that converts aldehydes and ketones into α-fluoro-α,β-unsaturated esters.

Yes. A Certificate of Analysis and Safety Data Sheet accompany each lot of SKU S1528, which is supplied to industrial and research customers who can meet its handling requirements.