107018-39-3

Usage

Uses

Used in Flavor and Fragrance Industry:
ETHYL 2-HYDROXY-2-(TRIFLUOROMETHYL)PROPANOATE is used as a flavoring agent and fragrance ingredient for its fruity odor, enhancing the sensory experience of consumer products such as perfumes, cosmetics, and cleaning agents.
Used in Pharmaceutical Synthesis:
ETHYL 2-HYDROXY-2-(TRIFLUOROMETHYL)PROPANOATE is used as a key intermediate in the synthesis of pharmaceuticals, contributing to the development of new medications and improving existing ones.
Used in Agrochemical Synthesis:
ETHYL 2-HYDROXY-2-(TRIFLUOROMETHYL)PROPANOATE is utilized in the synthesis of agrochemicals, playing a role in the development of products that protect and enhance crop yields and quality.

InChI:InChI=1/C6H9F3O3/c1-3-12-4(10)5(2,11)6(7,8)9/h11H,3H2,1-2H3

Upstream product

• 617-35-6 2-oxo-propionic acid ethyl ester 
• 75-63-8 Bromotrifluoromethane 
• 374-35-6 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid 
• 122-51-0 orthoformic acid triethyl ester 
• 64-17-5 ethanol 
• 13081-18-0 ethyl-3,3,3-trifluoropyruvate 
• 544-97-8 dimethyl zinc(II) 

Downstream Products

• 1262859-63-1 (R)-2-[(R)-2-(5-bromo-2-fluoro-phenyl)-2-(2-nitro-benzenesulfonylamino)-propoxy]-3,3,3-trifluoro-2-methyl-propionic acid ethyl ester 

Relevant academic research and scientific papers

The synthesis of (R)- and (S)-α-trifluoromethyl-α-hydroxycarboxylic acids via enzymatic resolutions

Kinetic resolution of 1, 1, 1-trifluoro-2-alkanone cyanohydrin acyl derivatives with Candida rugosa lipase afforded the remaining (R)-enantiomer in high selectivity (E from 30 to >200). Candida rugosa lipases from several suppliers were compared and found

Copper-catalyzed asymmetric methylation of fluoroalkylated pyruvates with dimethylzinc

The catalytic asymmetric methylation of fluoroalkylated pyruvates is shown with dimethylzinc as a methylating reagent in the presence of a copper catalyst bearing a chiral phosphine ligand. This is the first catalytic asymmetric methylation to synthesize various α-fluoroalkylated tertiary alcohols with CF3, CF2H, CF2Br, and n-CnF2n+1 (n = 2, 3, 8) groups in good-to-high yields and enantioselectivities. Axial backbones and substituents on phosphorus atoms of chiral phosphine ligands critically influence the enantioselectivity. Moreover, the methylation of simple perfluoroalkylated ketones is found to be facilitated by only chiral phosphines without copper.

Oxazolones as potent inhibitors of 11β-hydroxysteroid dehydrogenase type 1

2,5,5-Trisubstituted oxazolones were identified as potent inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1). The synthesis, structure-activity relationship and metabolic stability of these compounds are presented.

Reactions of Trifluoromethyl Bromide and Related Halides: Part 9. Comparison between Additions to Carbonyl Compounds, Enamines, and Sulphur Dioxide in the Presence of Zinc

A Barbier procedure, under moderate pressure, was used for the trifluoromethylation of various carbonyl compounds, starting from trifluoromethyl bromide and zinc in pyridine.Trifluoromethyl methanols were obtained from aldehydes and trifluoromethyl ketones from activated esters.Ethyl benzoate, or acetone, induced the formation of the solvated trifluoromethylzinc derivatives which did not react with carbonyl cpompounds.Consequently, the Barbier condensation in that case was considered to involve nascent organometallics reacting near the zinc surface.The reaction with sulphur dioxide, leading to trifluoromethanesulphinate, showed striking differences from that of carbonyl compounds.It was shown that the main pathway occcured in solution.This condensation was interpreted by the initial formation of sulphur dioxide radical anion, which reacts with trifluoromethyl bromide by a single-electron-transfer process.Attempts to condense iminium salts failed when a hydrogen atom was lacking in the α position.When the iminium ion can be transformed in situ to an enamine, a reaction occured, leading to α-trifluoromethyl ketones.This condensation was interpreted by a chain mechanism involving trifluoromethyl radicals.

Synthesis of Trifluoromethyl-substituted Methanols: a Barbier Procedure under Pressure

Synthesis of trifluoromethyl methanols can be achieved by stirring a mixture of carbonyl compound, zinc powder, and pyridine under a slight pressure of trifluoromethyl bromide.