349-43-9

Basic information

• Product Name: Ethyl 2-fluoropropionate
• Synonyms: ethyl 2-fluoropropanoate;2-fluoropropanoic acid ethyl ester;2-FLUOROPROPIONIC ACID ETHYL ESTER;Ethyl 2-fluoropropionate;2-fluoro-ethyl propionate
• CAS NO: 349-43-9
• Molecular Formula: C₅H₉FO₂
• Molecular Weight: 120.12
• EINECS: 206-478-9
• Product Categories: Fluorinated Building Blocks;Fluorinating Reagents & Building Blocks for Fluorinated Biochemical Compounds;Synthetic Organic Chemistry
• Mol File: 349-43-9.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 125°C
• Flash Point: 29°C
• Appearance: /
• Density: 0.997
• Vapor Pressure: 12.4mmHg at 25°C
• Refractive Index: 1.3750-1.3790
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: Ethyl 2-fluoropropionate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-fluoropropionate(349-43-9)
• EPA Substance Registry System: Ethyl 2-fluoropropionate(349-43-9)

Safety Data

• Hazard Codes: F
• Statements: 10-36/38
• Safety Statements: 16-36/37/39-3/9/49-26
• RIDADR: 3272
• HazardClass: FLAMMABLE
• PackingGroup: III
• Hazardous Substances Data: 349-43-9(Hazardous Substances Data)

Usage

Description

Ethyl 2-fluoropropionate, a clear colorless to light yellow liquid, is an organic compound with the molecular formula C5H9F. It is characterized by its unique chemical properties, making it a versatile substance in various applications.

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

• 33798-77-5 ethyl (S)-α-(4-methyl-phenylsulphonyloxy)-propionate 
• 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 
• 17344-99-9 AlaOEt 
• 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 

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 
• 17841-36-0 2-Fluor-2-methyl-3-phenyl-propionsaeureethylester 
• 881-41-4 2-fluoro-N-methyl-N-phenyl-butyramide 
• 21120-38-7 cyclohexyl 1-fluoroethyl ketone 
• 213322-87-3 2-amino-4-(1-fluoro-ethyl)-6-(1-phenyl-propyl-amino)-1,3,5-triazine 
• 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 

Relevant articles and documents

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.

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.

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.