Ethyl fluoroacetate

Base Information

• Chemical Name: Ethyl fluoroacetate
• CAS No.: 459-72-3
• Molecular Formula: C4H7FO2
• Molecular Weight: 106.097
• Hs Code.: 29159080
• European Community (EC) Number: 207-297-8
• NSC Number: 133459
• UNII: AUS1L6UM7B
• DSSTox Substance ID: DTXSID8060034
• Nikkaji Number: J26.229C
• Wikidata: Q27274128
• Mol file: 459-72-3.mol

Synonyms:ETHYL FLUOROACETATE;459-72-3;ethyl 2-fluoroacetate;Ethyl monofluoroacetate;Acetic acid, fluoro-, ethyl ester;Monofluoroacetic acid ethyl ester;Fluoroacetic Acid Ethyl Ester;Ethylester kyseliny fluoroctove;HSDB 2846;EINECS 207-297-8;UNII-AUS1L6UM7B;AUS1L6UM7B;NSC 133459;Ethylester kyseliny fluoroctove [Czech];BRN 1743761;MFCD00000450;NSC-133459;Fluoroacetic acid ethyl;ethyl 2-fluoranylethanoate;Ethyl fluoroacetate, 98%;FCH2C(O)OC2H5;Fluoracetic acid ethyl ester;WLN: F1VO2;SCHEMBL157691;fluoro-acetic acid ethyl ester;2-fluoroacetic acid ethyl ester;DTXSID8060034;VCYZVXRKYPKDQB-UHFFFAOYSA-;NSC133459;Acetic acid, 2-fluoro-, ethyl ester;AKOS006220713;FLUOROACETIC ACID ETHYL ESTER [MI];F0030;FT-0600005;A826947;Q27274128;F0001-1245

Chemical Property of Ethyl fluoroacetate

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 4.07mmHg at 25°C
• Refractive Index: n20/D 1.375(lit.)
• Boiling Point: 118 °C at 760 mmHg
• Flash Point: 30 °C
• PSA: 26.30000
• Density: 1.025 g/cm³
• LogP: 0.51900
• Storage Temp.: Flammables area
• Solubility.: water: soluble
• Water Solubility.: DECOMPOSES
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 106.04300762
• Heavy Atom Count: 7
• Complexity: 62.7

Purity/Quality:

99% ^*data from raw suppliers

Ethyl fluoroacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, T+
• Hazard Codes: T+,T,N
• Statements: 10-26/27/28-50-28
• Safety Statements: 13-36/37/39-45-28A-16-61-26-22-20

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: CCOC(=O)CF
• Description: Ethyl fluoroacetate is an ester organic solvent. It was used in the synthesis of 4-deoxy-4-fluoro-muscarines. It was used as starting reagent for the synthesis of ethyl(diethoxyphosphoryl)fluoroacetate. It was used in development of an ammonolysis-based microencapsulation process.
• Uses: Sodium salt as water-soluble rodenticide. Ethyl fluoroacetate is used in the synthesis of 4-deoxy-4-fluoro-muscarines. It is also used as starting reagent for the synthesis of ethyl(diethoxyphosphoryl)fluoroacetate. and in development of an ammonolysis-based microencapsulation process.

Technology Process of Ethyl fluoroacetate

There total 44 articles about Ethyl fluoroacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.46%

chloroacetic acid ethyl ester (105-39-5) → ethyl 2-fluoroacetate (459-72-3)

Guidance literature:

With potassium fluoride; 1-n-butyl-3-methylimidazolim bromide; In N,N-dimethyl-formamide; at 130 ℃; for 4h; Concentration; Reagent/catalyst; Time; Temperature;

Reference yield: 73.0%

1-hexene (592-41-6,25067-06-5) + ethyl 2-fluoro-2-iodoacetate (401-58-1) → ethyl 2-fluoroacetate (459-72-3) + Ethyl 2-fluorooctanoate (7740-65-0)

Guidance literature:

With pyridine; nickel dichloride; zinc; In tetrahydrofuran; at 60 ℃; for 3.5h; other alkenes, also with isopropyl iodofluoroacetate;

DOI:10.1016/0040-4039(92)88160-7

Reference yield: 71.0%

ethyl chlorofluoroacetate (401-56-9,96290-79-8) + 4-methoxycarbonylphenyl bromide (619-42-1) → ethyl 2-fluoroacetate (459-72-3) + C12H13FO4

Guidance literature:

With 2,6-dimethylpyridine; (1,2-dimethoxyethane)dichloronickel(II); tris(triethylsilyl)silane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine; In 1,2-dimethoxyethane; at 25 ℃; for 8h; Inert atmosphere; Sealed tube; Irradiation;

DOI:10.1002/anie.201909072

upstream raw materials:

diazoacetic acid ethyl ester

ethanol

fluoroacetamide

acetyl fluoride

Downstream raw materials:

ethyl 4,4,4-trifluoroacetoacetate

ethyl 2-fluoro-3-oxo-3-phenylpropionate

N-fluoroacetyl-phenylalanine ethyl ester

2-Fluor-bernsteinsaeure-diethylester

Refernces

• 1、 Chen, Tiffany Q.,MacMillan, David W. C.. "A Metallaphotoredox Strategy for the Cross-Electrophile Coupling of α-Chloro Carbonyls with Aryl Halides". supporting information. p. 14584 - 14588. Retrieved 2019/09/17.
• 2、 -. "Method for synthesizing fluoro ethyl acetate and fluoro methyl acetate". Paragraph 0025; 0026; 0027. . Retrieved 2016/10/07.