382-43-4

Basic information

• Product Name: 3-HYDROXY-2-TRIFLUOROMETHYLPROPIONIC ACID
• Synonyms: 3,3,3-trifluoro-2-(hydroxymethyl)propanoic acid;propanoic acid, 3,3,3-trifluoro-2-(hydroxymethyl)-;3-Hydroxy-2-(trifluoromethyl)propanoic acid;2-(Hydroxymethyl)-3,3,3-trifluoropropanoic acid, 3-Hydroxy-2-(trifluoromethyl)propionic acid;3-HYDROXY-2-TRIFLUOROMETHYLPROPIONIC ACID;2-(TRIFLUOROMETHYL)-3-HYDROXYPROPIONIC ACID;3-Hydroxy-2-(trifluoromethyl)propionic acid 97%;3-Hydroxy-2-(trifluoromethyl)propionicacid97%
• CAS NO: 382-43-4
• Molecular Formula: C₄H₅F₃O₃
• Molecular Weight: 158.08
• Mol File: 382-43-4.mol

Chemical Properties

• Boiling Point: 97 °C
• Flash Point: 119.1±27.3℃
• Appearance: /
• Density: 1.527±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.000739mmHg at 25°C
• Refractive Index: 1.382
• PKA: 2.84±0.11(Predicted)
• CAS DataBase Reference: 3-HYDROXY-2-TRIFLUOROMETHYLPROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXY-2-TRIFLUOROMETHYLPROPIONIC ACID(382-43-4)
• EPA Substance Registry System: 3-HYDROXY-2-TRIFLUOROMETHYLPROPIONIC ACID(382-43-4)

Safety Data

• Hazard Codes: C,Xn
• Statements: 34-36-22
• Safety Statements: 26-28-36/37/39
• RIDADR: 3265
• HazardClass: CORROSIVE
• Hazardous Substances Data: 382-43-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Hydroxy-2-trifluoromethylpropionic acid is used as a building block for the synthesis of various pharmaceuticals due to its unique reactivity and properties. The trifluoromethyl group enhances the pharmacological activity and selectivity of the resulting compounds, making it an essential component in the development of new drugs.
Used in Organic Synthesis:
In the field of organic synthesis, 3-Hydroxy-2-trifluoromethylpropionic acid is utilized as a versatile starting material for the preparation of a wide range of organic compounds. Its reactivity allows for various chemical transformations, enabling the synthesis of complex molecules with diverse applications.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
3-Hydroxy-2-trifluoromethylpropionic acid is employed as a chiral auxiliary in asymmetric synthesis, where it plays a key role in controlling the stereochemistry of the final compound. Its ability to induce enantioselectivity in chemical reactions is highly valuable in the synthesis of enantiomerically pure compounds, which are often required for biological activity and pharmaceutical applications.
Used in Research Settings:
In research, 3-Hydroxy-2-trifluoromethylpropionic acid is utilized for exploring new chemical reactions and developing innovative synthetic methodologies. Its unique properties and reactivity make it an attractive candidate for studying reaction mechanisms and developing new catalytic systems, contributing to the advancement of organic chemistry.

InChI:InChI=1/C4H5F3O3/c5-4(6,7)2(1-8)3(9)10/h2,8H,1H2,(H,9,10)

Upstream product

• 381-84-0 2-(trifluoromethyl)acrylonitrile 
• 432-15-5 β,β,β-trifluoro-β'-hydroxy-isobutyric acid amide 
• 382-41-2 β'-chloro-β,β,β-trifluoro-isobutyric acid amide 
• 381-98-6 trifluoromethyacrylic acid 

Downstream Products

• 381-98-6 trifluoromethyacrylic acid 
• 359-88-6 β,β,β-trifluoro-β'-methoxy-isobutyric acid methyl ester 

Relevant articles and documents

Preparation of Trifluoromethylated Compounds by Anodic Oxidation of 3-Hydroxy-2-trifluoromethylpropionic Acid

Electrochemical Oxidation of 3-hydroxy-2-trifluoromethylpropionic acid (1) produced 2,3-bis(trifluoromethyl)-1,4-butanediol in quantitative yield.Furthermore, 2-trifluromethylated alcohols were obtained by the crossed Kolbe reaction of 1 with carboxylic acids or dicarboxylic acid mono esters.

Two Scalable Syntheses of 3-(Trifluoromethyl)cyclobutane-1-carboxylic Acid

Two efficient synthetic methods for preparation of 3-(trifluoromethyl)cyclobutane-1-carboxylic acid are reported starting from readily available 4-oxocyclobutane precursors. These cyclobutanones can be converted to their CF3 carbinols upon treatment with TMSCF3 and a fluoride source. The bis-carboxylate system 9 was deoxygenated by treatment of Bu3SnH and provided desired compound 1 upon decarboxylation. In the monocarboxylate system 15, the triflate could be efficiently eliminated; subsequent hydrogenation afforded cis-1.

Preparation of (R)- and (S)-3-Hydroxy-2-(trifluoromethyl)propionic Acid by Resolution with (R,R)- and (S,S)-2-Amino-1-phenylpropane-1,3-diol

Racemic 2-trifluoromethyl-3-hydroxypropionic acid (rac-1) is prepared on a 50 g scale from 3,3,3-trifluoropropene in four steps, the overall yield being 40percent.A procedure for the resolution of rac-1 with 2-amino-1-phenylpropane-1,3-diol is described (25 g scale).The acids (R)-1 and (S)-1 are isolated, their enantiomer purities determined by GC analysis of the corresponding methyl esters on a chiral column and their chirality senses assigned from an X-ray crystal structure of the salt formed with phenylethylamine.The non-fluorinated analog of 1 is frequently employed as a chiral synthetic building block ("Roche acid").