349-43-9

Usage

Uses

1. Used in the Chemical Industry:
Ethyl 2-fluoropropionate is used as a reagent for the synthesis of a series of potent Nicotinic Acid (N429250) receptor agonists. These agonists are crucial in the treatment of dyslipidemia, a health condition characterized by high triglyceride levels. Ethyl 2-fluoropropionate's ability to act as a reagent in the synthesis of these agonists highlights its importance in the development of pharmaceuticals for treating dyslipidemia.
2. Used in the Energy Industry:
Ethyl 2-fluoropropionate is utilized as a solvent for lithium secondary batteries. Its properties make it suitable for use in the energy storage sector, contributing to the development and improvement of lithium-ion batteries, which are widely used in various electronic devices and electric vehicles.

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 2311, 1990 DOI: 10.1021/jo00295a016

InChI:InChI=1/C5H9FO2/c1-3-8-5(7)4(2)6/h4H,3H2,1-2H3

Upstream product

• 97-64-3 ethyl 2-hydroxypropionate 
• 64-17-5 ethanol 
• 430-71-7 propionyl fluoride 
• 430-97-7 (R,S)-2-Fluoropropanoyl chloride 
• 55816-57-4 ethyl (RS)-2-(trimethylsilyloxy)propionate 
• 97299-38-2 boric acid tris-(1-ethoxycarbonyl-ethyl ester) 
• 535-11-5 Ethyl 2-bromopropionate 
• 58742-64-6 ethyl l-2-((methylsulfonyl)oxy)propionate 
• 1006904-67-1 tris(dimethylamino)methylium trifluoromethanolate 
• 77902-90-0 rac-2-(Trifluormethylsulfonyloxy)propionsaeure-ethylester 
• 2700-82-5 cesium trifluoromethoxide 
• 96898-10-1 tris(dimethylamino)sulfonium trifluoromethoxide 
• 535-13-7 2-chloro-propanoic acid, ethyl ester 
• 1550-50-1 1,1,2,2-tetrafluoro-N,N-dimethylethan-1-amine 

Downstream Products

• 21120-36-5 1-fluoroethyl phenyl ketone 
• 29114-73-6 1,1-diphenyl-2-fluoro-1-propanol 
• 3824-87-1 2-fluoro-1-hydroxypropane 
• 55816-69-8 ethyl 2-fluoro-isobutyrate 
• 57965-29-4 2-fluoropropanoic acid 
• 1402412-87-6 (2S,3R)-2-fluoro-3-(2-fluoro-phenyl)-2-methyl-3-((R)-2-methyl-propane-2-sulfinylamino)-butyric acid ethyl ester 
• 1402412-88-7 (2R,3R)-2-fluoro-3-(2-fluoro-phenyl)-2-methyl-3-((R)-2-methyl-propane-2-sulfinylamino)-butyric acid ethyl ester 
• 879551-04-9 (3R,4R,5R)-3?fluoro?4?hydroxy?5?(hydroxymethyl)?3?methyltetrahydrofuran?2?one 
• 1040882-61-8 (3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one 
• 213322-87-3 2-amino-4-(1-fluoro-ethyl)-6-(1-phenyl-propyl-amino)-1,3,5-triazine 
• 21120-38-7 cyclohexyl 1-fluoroethyl ketone 
• 881-41-4 2-fluoro-N-methyl-N-phenyl-butyramide 
• 17841-36-0 2-Fluor-2-methyl-3-phenyl-propionsaeureethylester 

Relevant academic research and scientific papers

Fluorinating agent and synthesis method thereof

The invention discloses a fluorinating agent, and also discloses a preparation method of the fluorinating agent, wherein an amide corresponding to the structural formula of the product reacts with a halogenating agent to obtain corresponding alpha, alpha-dihaloamine, and the alpha, alpha-dihaloamine reacts with a fluoride to obtain the corresponding fluorinating agent. The fluorinating agent has the advantages of being stable in storage and capable of fluorinating hydroxyl with high yield, the preparation method is simple, the adopted raw materials are easy to obtain, the synthesis yield is high, and the fluorinating efficiency of the obtained product is high.

Method for co-producing 2-fluoropropionate and ethyl difluoroacetate

The invention discloses a method for co-producing 2-fluoropropionate and ethyl difluoroacetate. The method comprises: (a) carrying out a reaction on a fluorinating reagent and a lactate for 0.5-7 h ata reaction temperature of 30-120 DEG C according to a molar ratio of 0.5-2:1, cooling the reaction material after completing the reaction, adding a nitrogen-containing compound, and carrying out pressure reducing rectification to obtain a 2-fluoropropionate product and N,N-dimethyl difluoroacetamide; and (b) adding concentrated sulfuric acid to a mixture of anhydrous ethanol and the N,N-dimethyldifluoroacetamide obtained in the step (a), carrying out a reaction for 1-10 h at a reaction temperature of 50-170 DEG C, cooling after completing the reaction, separating the liquid, and carrying outrectification to obtain the ethyl difluoroacetate product, wherein a molar ratio of anhydrous ethanol to N,N-dimethyl difluoroacetamide is 0.5-4.5:1, and a molar ratio of concentrated sulfuric acid to N,N-dimethyl difluoroacetamide is 0.1-1.5:1. According to the present invention, the method has advantages of environmental protection, high yield and low cost.

Prototypic 18F-Labeled Argininamide-Type Neuropeptide Y Y1R Antagonists as Tracers for PET Imaging of Mammary Carcinoma

The neuropeptide Y (NPY) Y1 receptor (Y1R) selective radioligand (R)-Nα-(2,2-diphenylacetyl)-Nω-[4-(2-[18F]fluoropropanoylamino)butyl]aminocarbonyl-N-(4-hydroxybenzyl)argininamide ([18F]23), derived from the high-affinity Y1R antagonist BIBP3226, was developed for imaging studies of Y1R-positive tumors. Starting from the argininamide core bearing amine-functionalized spacer moieties, a series of fluoropropanoylated and fluorobenzoylated derivatives was synthesized and studied for Y1R affinity. The fluoropropanoylated derivative 23 displayed high affinity (Ki = 1.3 nM) and selectivity toward Y1R. Radiosynthesis was accomplished via 18F-fluoropropanoylation, yielding [18F]23 with excellent stability in mice; however, the biodistribution study revealed pronounced hepatobiliary clearance with high accumulation in the gall bladder (>100 %ID/g). Despite the unfavorable biodistribution, [18F]23 was successfully used for imaging of Y1R positive MCF-7 tumors in nude mice. Therefore, we suggest [18F]23 as a lead for the design of PET ligands with optimized physicochemical properties resulting in more favorable biodistribution and higher Y1R-dependent enrichment in mammary carcinoma.

A 2 - fluorination ester synthesis method

The invention discloses a 2-fluoropropionate synthetizing method. The method comprise the steps of 1, adding ester to a four-mouth flask provided with a condenser pipe, wherein the general formula of the ester is CH3CHXCOOR, and R represents alkyl; 2, adding an addition agent, a catalyst and solvent to the four-mouth flask, and then adding a fluorinated reagent and conducting stirring to obtain reaction liquid; 3, heating the reaction liquid to a set temperature, wherein reaction time is 3-16 h; 4, conducting rectification after reaction ends to obtain a 2-fluoropropionate target product. According to the method, cheap 2-CH3CHClCOOR is used as the raw material, and fluorination is conducted with potassium fluoride in the presence of the addition agent to obtain the 2-fluoropropionate. The method has the advantages that the reaction condition is mild, the yield is high, and cost is low. Due to the fact that the addition agent is added, generation of high-boiling by-products can be restrained, and then reaction selectivity is improved.

Nucleophilic fluorination of triflates by tetrabutylammonium bifluoride

(Chemical Equation Presented) Careful examination of nucleophilicity, basicity, and leaving group ability led us to discover the nucleophilic fluorination of triflates by weakly basic tetrabutylammonium bifluoride, which provides excellent yields with minimal formation of elimination-derived side products. Primary hydroxyl groups as well as secondary hydroxyl groups in acyclic chains or in five-membered rings are excellent substrates, whereas benzylic and aldol-type secondary hydroxyl groups give poor yields as a result of the instability of their triflates.

Versatile application of trifluoromethyl triflate

Hydrolytically stable and easy to handle trifluoromethyl triflate was found to be a liquid reservoir of 'masked' difluorophosgene. Anhydrous F- sources cleave the S-O bond in trifluoromethyl triflate yielding quantitatively the trifluoromethanolate salts, being useful trifluoromethoxy group carriers. Reaction of trifluoromethanolates with in situ generated from o-trimethylsilylphenyl triflate benzyne leads to (trifluoromethoxy)benzene and fluorobenzene (ratio 85:15). Whereas an addition of trifluoromethanethiolate anion across a triple bond of benzyne leads to [(trifluoromethyl)sulfanyl]benzene solely.

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.

Fluorinating reactants and process for their preparation

alpha,alpha-Difluoroalkylamines (I) are new. Also new are mixtures (A) containing (a) a broader class of alpha,alpha-difluoroalkylamines (I'), (b) an aprotic tertiary amine having no fluoro atoms in the alpha-position relative to nitrogen and/or a N-heteroaromatic compound and (c) hydrogen fluoride; and some specific dichloro compound intermediates. alpha,alpha-Difluoroalkylamines of formula R1-CF2-NR2R3 (I) are new. R1 = H, 1-12C alkyl, ((2-12C) alkylene-O)n-(1-12C) alkyl, 4-15C aralkyl or 3-14C heteroaryl; n = 1-5; R2, R3 = 4-15C aralkyl or 1-12C alkyl; or R2 + R3 or R1 + R2 and/or R3 = group completing a 3-12C cyclic group; the compounds 1,1-difluoromethyl-N,N-dimethylamine, 1,1-difluoromethyl-N,N-diethylamine, 1,1-difluoromethyl-N,N-diisopropylamine and 1,1-difluoro-N,N-2-trimethyl-1-propanamine are excluded. Independent claims are included for: (a) new mixtures (A) comprising (a) alpha,alpha-difluoroalkylamines of formula R4-CF2-NR5R6 (I'), (b) at least one aprotic tertiary amine having no fluoro atoms in the alpha-position relative to the nitrogen and/or at least one N-heteroaromatic compound and (c) hydrogen fluoride; (b) the preparation of (I) and (A); and (c) the following new geminal dichloro compound intermediates: 1,1-dichloromethyl-N,N-dimethylamine, 1,1-dichloromethyl-N,N-diethylamine, 1,1-dichloromethyl-N,N-diisopropylamine, 1,1-dichloro-N,N-2-trimethyl-1-propanamine, 1,1-dichloro-N,N-2,2-tetramethyl-1-propanamine (VIa), N,N-diethyl-alpha,alpha-dichloro-2,2-dimethyl-1-propanamine, N-(1,1-dichloromethyl)-morpholine, 1,1-dichloro-N,N-dimethyl-phenylmethanamine, N,N-diethyl-alpha,alpha-dichloro-3-pyridyl-methanamine and 2,2-dichloro-1,3,3-trimethylpyrrolidine. R4 = H, 1-12C alkyl, ((2-12C) alkylene-O)n-(1-12C) alkyl, 3-14C aryl or NR7R8; n = 1-5; R7, R8 = 1-8C alkyl; or NR7R8 = 4-7 membered cyclic residue with a total of 3-12C; R5, R6 = 1-12C alkyl; or R5 + R6 or R4 + R5 and/or R6 = group completing a 4-12C cyclic group.

A semi-molten mixture of hexadecyltributylphosphonium bromide and potassium fluoride in the synthesis of organofluorine compounds

A facile and effective reagent system comprising of a semi-molten mixture of hexadecyltributylphosphonium bromide and potassium fluoride has been developed and its scope has been investigated in nucleophilic fluoride exchange with various organohalides. This simple and convenient reagent system provides organofluorine compounds in high yields even with haloesters in which fluoride catalysed elimination is also feasible.

Bis(2-methoxyethyl)aminosulfur trifluoride: A new broad-spectrum deoxofluorinating agent with enhanced thermal stability

Bis(2-methoxyethyl)aminosulfur trifluoride (Deoxo-Fluor) is effective for the conversion of alcohols to alkyl fluorides, aldehydes/ketones to the corresponding gem-difluorides and also for the transformation of carboxylic acids to their trifluoromethyl derivatives; it is a less thermally sensitive, broader-spectrum alternative to the traditional dialkylaminosulfur trifluoride (DAST) deoxofluorination reagents.