459-72-3

Basic information

• Product Name: Ethyl fluoroacetate
• Synonyms: ETHYL FLUOROACETATE;ETHYL MONOFLUOROACETATE;FLUOROACETIC ACID ETHYL ESTER;Aceticacid,fluoro-,ethylester;Ethylester kyseliny fluoroctove;ethylesterkyselinyfluoroctove;Fluoracetic acid ethyl ester;fluoro-aceticaciethylester
• CAS NO: 459-72-3
• Molecular Formula: C₄H₇FO₂
• Molecular Weight: 106.1
• EINECS: 207-297-8
• Product Categories: Fluoro-Aliphatics ;Fluorinated Building Blocks;Fluorinating Reagents & Building Blocks for Fluorinated Biochemical Compounds;Synthetic Organic Chemistry;C2 to C5;Carbonyl Compounds;Esters
• Mol File: 459-72-3.mol

Chemical Properties

• Boiling Point: 119.3 °C753 mm Hg(lit.)
• Flash Point: 86 °F
• Appearance: Colorless to pale yellow/Liquid
• Density: 1.098 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.07mmHg at 25°C
• Refractive Index: n20/D 1.375(lit.)
• Storage Temp.: Flammables area
• Solubility: water: soluble
• Water Solubility: DECOMPOSES
• Merck: 14,4167
• BRN: 1743761
• CAS DataBase Reference: Ethyl fluoroacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl fluoroacetate(459-72-3)
• EPA Substance Registry System: Ethyl fluoroacetate(459-72-3)

Safety Data

• 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
• RIDADR: UN 2929 6.1/PG 1
• WGK Germany: 3
• RTECS: AH7175000
• F: 21
• TSCA: Yes
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 459-72-3(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

Different sources of media describe the Uses of 459-72-3 differently. You can refer to the following data:
1. Sodium salt as water-soluble rodenticide.
2. 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.

Application

Ethyl fluoroacetate is an inhibitor of insect juvenile hormone biosynthesis. It also shows toxic effects against Vibrio fischeri.

General Description

Ethyl fluoroacetate is an ester organic solvent.

InChI:InChI=1/C6H4BrF/c7-5-1-3-6(8)4-2-5/h1-4H

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 64-17-5 ethanol 
• 640-19-7 fluoroacetamide 
• 557-99-3 acetyl fluoride 
• 682-86-0 ethyl-(1,1,2-trifluoro-ethyl)-ether 
• 105-39-5 chloroacetic acid ethyl ester 
• 105-36-2 ethyl bromoacetate 
• 623-48-3 ethyl iodoacetae 
• 392-58-5 Diethyl fluoroxaloacetate 
• 6043-54-5 2-ethoxy-(2-fluoromethyl)styrene 
• 557-31-3 3-ethoxyprop-1-ene 
• 401-58-1 ethyl 2-fluoro-2-iodoacetate 
• 78-94-4 methyl vinyl ketone 
• 401-55-8 ethyl bromofluoroacetate 

Downstream Products

• 332-21-8 2-fluoro-5t-phenyl-penta-2ξ,4-dienoic acid 
• 330-80-3 ethyl 2-fluoro-3-phenylpropanoate 
• 587-66-6 fluoro-acetic acid cyclohexylamide 
• 20397-61-9 (Z)-2-fluoro-3-phenylacrylic acid 
• 396-22-5 α-fluoro-trans-cinnamaldehyde-(2,4-dinitro-phenylhydrazone) 
• 1479-22-7 ethyl 2-fluoro-3-oxo-3-phenylpropionate 
• 372-37-2 ethyl 4-fluoro-3-oxo-butanoate 
• 337-98-4 ethyl 1-fluorocyclobutanecarboxylate 
• 352-20-5 1-fluoro-2,4-pentanedione 
• 427-31-6 ethyl 2-fluoro-3-hydroxy-3,3-diphenylpropanoate 
• 709-15-9 α-Fluor-2-hydroxy-zimtsaeure 
• 5942-73-4 Aethyl-<1-fluormethyl-4-phenyl-buten-(1)-yl>-aether 
• 817-95-8 ethyl 2-ethoxyethanoate 
• 18009-48-8 3-Benzyloxyimino-2-fluor-propionsaeure-ethylester 

Relevant articles and documents

Nickel-Catalyzed Cross-Coupling of Ethyl Chlorofluoroacetate with Aryl Bromides

A combinatorial nickel-catalyzed monofluoroalkylation of aryl bromides with the industrial raw regent ethyl chlorofluoroacetate has been developed. The two key factors to successful conversion are the combination of nickel with readily available nitrogen and phosphine ligands and the using of a mixture of different solvents. Mechanistic investigations indicated a new zinc regent might generated in situ and be involved in the reaction process.

A Metallaphotoredox Strategy for the Cross-Electrophile Coupling of α-Chloro Carbonyls with Aryl Halides

Here, we demonstrate that a metallaphotoredox-catalyzed cross-electrophile coupling mechanism provides a unified method for the α-arylation of diverse activated alkyl chlorides, including α-chloroketones, α-chloroesters, α-chloroamides, α-chlorocarboxylic acids, and benzylic chlorides. This strategy, which is effective for a wide variety of aryl bromide coupling partners, is predicated upon a halogen atom abstraction/nickel radical-capture mechanism that is generically successful across an extensive range of carbonyl substrates. The construction and use of arylacetic acid products have further enabled two-step protocols for the delivery of valuable building blocks for medicinal chemistry, such as aryldifluoromethyl and diarylmethane motifs.

A Gas Chromatography-Mass Spectrometry Method for the Detection and Quantitation of Monofluoroacetate in Plants Toxic to Livestock

Monofluoroacetate (MFA) is a potent toxin that occurs in over 50 plant species in Africa, Australia, and South America and is responsible for significant livestock deaths in these regions. A gas chromatography-mass spectrometry (GC-MS) method for the analysis of MFA in plants based on the derivatization of MFA with n-propanol in the presence of sulfuric acid to form propyl fluoroacetate was developed. This method compared favorably to a currently employed high-performance liquid chromatography-mass spectrometry (HPLC-MS) method for the analysis of MFA in plants. The GC-MS method was applied to the analysis of MFA in herbarium specimens of Fridericia elegans, Niedenzuella stannea, N. multiglandulosa, N. acutifolia, and Aenigmatanthera lasiandra. This is the first report of MFA being detected in F. elegans, N. multiglandulosa, N. acutifolia, and A. lasiandra, some of which have been reported to cause sudden death or that are toxic to livestock.

Method for synthesizing fluoro ethyl acetate and fluoro methyl acetate

The invention provides a method for synthesizing fluoro ethyl acetate or fluoro methyl acetate. According to the method, chloro-alkyl imidazole ionic liquid and/or bromo-alkyl imidazole ionic liquid is taken as the catalyst, ethyl chloroacetate or ethyl chloroacetate and alkali metal fluorides are taken as raw materials, a polar aprotic solvent is taken as the reaction medium, filtration is conducted after reaction is conducted for a while at a set temperature to remove inorganic salt, and then fluoro ethyl acetate or fluoro methyl acetate is obtained.

Activation reactions of 1,1-dialkoxoalkanes and unsaturated O-donors by titanium tetrafluoride

The reactivity of TiF4 with a variety of non cyclic 1,1-dialkoxoalkanes [CH2(OR)2, R = Me, Et, Me 2C(OMe)2, MeCH(OEt)2, ClCH2CH(OEt) 2, CH(OMe)3, PhCCCH(OEt)2], 1,3-dioxolane, N2CHCO2Et and 1,2-epoxybutane has been investigated. Activation, including fragmentation and/or rearrangement of the organic moiety, has been observed at room temperature in some cases; it generally occurs unselectively via C-O bond fission and the formation of new C-O, C-H and C-C bonds. Small differences in the structure of the organic substrate may determine significant differences in the reactivity with TiF4.

PRODUCTION OF COMPOUNDS COMPRISING CF30 GROUPS

The present invention relates to a process for the preparation of compounds containing CF3O groups using compounds containing at least one group Y, in which Y=—Hal, —OSO2(CF2)zF, —OSO2CzH2z+1 (z=1-10), —OSO2F, —OSO2Cl, —OC(O)CF3— or —OSO2Ar, to a process for the preparation of compounds containing CF3O groups using KOCF3 and/or RbOCF3, and to novel compounds containing CF3O groups, and to the use thereof.

Palladium-catalyzed cross-coupling of ethyl α-bromo-α- fluoroacetate with arylboronic acids: Facile synthesis of α-aryl-α- fluoroacetate

Palladium-catalyzed Suzuki-Miyaura coupling reactions of ethyl α-bromo-α-fluoroacetate with various structurally diverse arylboronic acids using a phosphine ligand proceeded smoothly to afford α-aryl-α-fluoroacetate in moderate to good yields. This method provides a practical and efficient route to diverse α-monofluorinated α-arylcarbonyl compounds. Georg Thieme Verlag Stuttgart New York.

Cocatalysis in phase-transfer catalyzed fluorination of alkyl halides and sulfonates

Phase-transfer catalyzed (PTC) fluorination of alkyl halides and sulfonates with solid KF proceeds efficiently when cocatalyst triphenyltin fluoride is used. The cocatalytic action of the tin compound consists in continuous formation of difluorotriphenylstannate anion that as the tetraalkyloammonium salt enter the solution where it reacts with alkyl halides to produce alkyl fluorides. The cocatalytic system was used to synthesis of 1,1-difluoroalkanes in two steps from aldehydes. A new kind of PTC was elaborated in which Ph 3SnF acts as phase transfer catalyst via continuous formation of potassium salts of diflurotriphenylstannate anions soluble in dipolar aprotic solvents. A new, simple and general method of synthesis of tetraalkylammonium and potassium salts of difluorotriorgano-tin, silicon and germanium anions is reported.

Pyrimidine compounds

5-Bromo-2-iodopyrimidine is used to synthesize a range of chemical compounds including liquid crystalline compounds.

Alkylation and decarboxylation of ethyl 2-fluoro-3-oxobutanoate as a route to functionalised α-fluoro-ketones

Alkylation and decarboxylation of α-fluoro-β-ketoesters such as ethyl 2-fluoro-3-oxobutanoate offers a versatile route to a range of fluoro-ketoalkenes, demonstrating the synthetic utility of using α-fluoro-β-ketoesters as synthons for the preparation of synthetically more sophisticated selectively fluorinated systems.