127306-59-6

Basic information

• Product Name: Ethyl 2-fluoropropionate
• Synonyms: AKOS 91139;AKOS BBS-00003628;LABOTEST-BB LTBB000714;FLUOROANILINE-2
• CAS NO: 127306-59-6
• Molecular Formula: C6H6FN
• Molecular Weight: 111.12
• EINECS: 206-478-9
• Mol File: 127306-59-6.mol

Chemical Properties

• Melting Point: −29 °C(lit.)
• Boiling Point: 182-183 °C(lit.)
• Flash Point: 140 °F
• Appearance: Light-yellowish liquid
• Density: 1.151 g/mL at 25 °C(lit.)
• Vapor Pressure: 12.4mmHg at 25°C
• Refractive Index: n20/D 1.544(lit.)
• CAS DataBase Reference: Ethyl 2-fluoropropionate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-fluoropropionate(127306-59-6)
• EPA Substance Registry System: Ethyl 2-fluoropropionate(127306-59-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• RIDADR: UN 2941 6.1/PG 3
• WGK Germany: 2
• Hazardous Substances Data: 127306-59-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Ethyl 2-fluoropropionate is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drug molecules. Its unique chemical structure allows for the creation of fluorinated compounds, which can enhance the pharmacokinetic and pharmacodynamic properties of drugs.
Used in Agrochemical Production:
In the agrochemical industry, Ethyl 2-fluoropropionate is employed as a building block in the production of pesticides and other crop protection agents. Its incorporation into these compounds can improve their effectiveness and selectivity, leading to better agricultural outcomes.
Used as a Solvent in Chemical Reactions:
Ethyl 2-fluoropropionate is utilized as a solvent in a variety of chemical reactions due to its ability to dissolve a wide range of substances. Its use as a solvent can facilitate reaction rates and improve the yield of desired products in chemical processes.
Used in Organic Synthesis as a Precursor:
Ethyl 2-fluoropropionate is studied for its potential as a precursor in organic synthesis, where it can be used to form more complex molecules. Its presence in these reactions can lead to the development of novel compounds with specific applications in various industries.
Used in Research and Development:
In research settings, Ethyl 2-fluoropropionate is employed to explore new chemical reactions and pathways, contributing to the advancement of scientific knowledge and the discovery of innovative applications in multiple fields.

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

Upstream product

• 33798-77-5 ethyl (S)-α-(4-methyl-phenylsulphonyloxy)-propionate 
• 64-17-5 ethanol 
• 430-71-7 propionyl fluoride 
• 430-97-7 (R,S)-2-Fluoropropanoyl chloride 
• 97299-38-2 boric acid tris-(1-ethoxycarbonyl-ethyl ester) 
• 535-11-5 Ethyl 2-bromopropionate 
• 55816-57-4 ethyl (RS)-2-(trimethylsilyloxy)propionate 
• 51063-99-1 (R)-ethyl 2-bromopropanoate 
• 687-47-8 (S)-Ethyl lactate 
• 94721-39-8 (R)-(+)-2-fluoro-2-methylmalonic acid monoethyl ester 
• 102712-69-6 (R)-(+)-ethyl 3-hydroxy-2-fluoropropionate 
• 685-88-1 fluoromalonic acid diethyl ester 
• 102712-70-9 (R)-2-Fluoro-3-(toluene-4-sulfonyloxy)-propionic acid ethyl ester 
• 63696-99-1 (S)-ethyl 2-(methylsulfonyloxy)propanoate 

Downstream Products

• 881-41-4 2-fluoro-N-methyl-N-phenyl-butyramide 
• 876747-18-1 (2R)-2-fluoropropanol 
• 57965-29-4 2-fluoropropanoic acid 
• 55816-69-8 ethyl 2-fluoro-isobutyrate 
• 3824-87-1 2-fluoro-1-hydroxypropane 
• 29114-73-6 1,1-diphenyl-2-fluoro-1-propanol 

Relevant articles and documents

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 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.

PROCESS FOR PREPARING 2-FLUOROPROPIONALDEHYDE

A process comprising (i) providing a 2-fluoropropionic acid halide; (ii) hydrogenating the 2-fluoropropionic acid halide by contacting it with a heterogeneous hydrogenation catalyst in an atmosphere comprising hydrogen, obtaining a mixture comprising 2-fluoropropionic aldehyde.

PROCESS FOR PRODUCING -SUBSTITUTED ESTER

There is provided a process for producing an α-substituted ester by reaction of a fluorosulfuric acid ester of α-hydroxyester with a Grignard reagent in the presence of a zinc catalyst. It is newly found that the reaction for production of α-substituted e

DEHYDROXYLATED FLUORINATING AGENT

There is provided a novel, useful dehydroxyfluorination agent containing sulfuryl fluoride (SO2F2) and an organic base that is free from a free hydroxyl group in the molecule. According to the present dehydroxyfluorination agent, it is not necessary to use perfluoroalkanesulfonyl fluoride, which is not preferable in large-scale use, and it is possible to advantageously produce optically-active fluoro derivatives, which are important intermediates of medicines, agricultural chemicals and optical materials, for example, 4-fluoroproline derivatives, 2'-deoxy-2'-fluorouridine derivatives, optically-active α-fluorocarboxylate derivatives, and monofluoromethyl derivatives, even in large scale.

PROCESS FOR THE MANUFACTURE OF FLUORINATED COMPOUNDS

A process for the manufacture of a fluorinated organic compound of formula R-F wherein R is an organic residue, which comprises reacting a starting material of general formula R-X wherein X is a leaving group with SO2F2. Addition of

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.