114715-77-4

Basic information

• Product Name: 2-(TRIFLUOROMETHYL)-2-HYDROXYPROPIONIC ACID
• Synonyms: 2-HYDROXY-2-(TRIFLUOROMETHYL)PROPIONIC ACID;2-(TRIFLUOROMETHYL)-2-HYDROXYPROPIONIC ACID;2-(TRIFLUOROMETHYL)LACTIC ACID;3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID;3,3,3-TRIFLUORO-2-HYDROXYISOBUTYRIC ACID;RARECHEM AL BO 0412;TFM-LA;2-(Trifluoromethyl)-2-hydroxypropionic acid~2-(Trifluoromethyl)lactic acid
• CAS NO: 114715-77-4
• Molecular Formula: C₄H₅F₃O₃
• Molecular Weight: 158.08
• EINECS: -0
• Mol File: 114715-77-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 85°C
• Boiling Point: 189°C
• Flash Point: 189°C
• Appearance: /
• Density: 1.532 g/cm³
• BRN: 1723691
• CAS DataBase Reference: 2-(TRIFLUOROMETHYL)-2-HYDROXYPROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(TRIFLUOROMETHYL)-2-HYDROXYPROPIONIC ACID(114715-77-4)
• EPA Substance Registry System: 2-(TRIFLUOROMETHYL)-2-HYDROXYPROPIONIC ACID(114715-77-4)

Safety Data

• Hazard Codes: Xi,C
• Statements: 34
• Safety Statements: 26-36/37/39
• RIDADR: 3265
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 114715-77-4(Hazardous Substances Data)

Usage

General Description

2-(Trifluoromethyl)-2-hydroxypropionic acid is a chemical compound characterized by the presence of both trifluoromethyl and carboxylic acid functional groups. This molecule is structurally similar to other alpha-hydroxy acids (AHAs), which are widely used in the cosmetics industry for their exfoliating and skin-smoothing properties. Its trifluoromethyl group increases the compound's stability and lipophilicity, potentially enhancing its skin absorption. Despite these desirable properties, there is limited information available about this specific compound's use or safety in cosmetic or other formulations, necessitating further research.

Upstream product

• 374-35-6 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid 
• 337-16-6 2-hydroxy-2-methyl-3,3,3-trifluoropropionic acid methyl ester 
• 114645-34-0 (R,S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide 
• 693287-30-8 (R)-2,3-epoxy-2-(trifluoromethyl)propionic acid 

Downstream Products

• 1360607-89-1 4-((3-chloro-4-(3,3,3-trifluoro-2-hydroxy-2-methylpropanamido)phenyl)thio)N,N-dimethylbenzamide 
• 329925-77-1 (2R)-N-[2-chloro-4-(ethylsulfonyl)-3-fluorophenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide 
• 1310351-08-6 {(R)-5,5-difluoro-4-[2-fluoro-5-((R)-3,3,3-trifluoro-2-hydroxy-2-methyl-propionylamino)-phenyl]-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-yl}-carbamic acid tert-butyl ester 
• 329794-58-3 (R)-[5-(4-methylsulphanylphenylsulphanyl)-1-(3,3,3-trifluoro-2-hydroxy-2-methylpropionyl)indoline] 
• 329926-82-1 (R)-N-(2-methyl-3-fluoro-4-iodophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide 
• 243982-46-9 (R)-N-(2-Chlorophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide 
• 329901-81-7 (R)-N-(3-nitro-2-chlorophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide 
• 329901-77-1 (R)-N-{2-chloro-3-methylphenyl}-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide 
• 242139-87-3 (R)-N-[2-chloro-4-iodophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide 
• 329901-38-4 (R)-N-(2,5-Dimethoxy-4-[dimethylaminosulphonyl]phenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide 
• 329901-37-3 (R)-N-(4-[Anilinosulphonyl]-2,5-dimethoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide 
• 242139-91-9 (R)-N-[2-chloro-4-(phenylsulphanyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide 

Relevant articles and documents

Efficient preparation of both enantiomers of 3,3,3-trifluoro-2-hydroxy-2- methylpropanoic acid catalyzed by Shinella sp. R-6 and Arthrobacter sp. S-2

Several microorganisms that can enantioselectively hydrolyze 3,3,3-trifluoro-2-hydroxy-2-methylpropanamide have been isolated from soil samples. These strains were capable of growing in a medium containing 3,3,3-trifluoro-2-hydroxy-2-methylpropanamide as the sole nitrogen source. Among them, Shinella sp. R-6 was identified as a strain capable of exhibiting R-selective hydrolysis activity, while Arthrobacter sp. S-2 was capable of exhibiting S-selective hydrolysis activity. The preparation of both enantiomers of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid via the two-step whole-cell reaction was investigated using these two strains.

Substituted N-phenyl 2-hydroxy-2-methyl-3,3,3-trifluoropropanamide derivatives which elevate pyruvate dehydrogenase activity

A compound of formula (I) wherein: n is 1 or 2; R 1 is chloro, fluoro, bromo, methyl or methoxy; R 2 is as defined within; R 3 is as defined within; and R 4 is hydrogen or fluoro; or a pharmaceutically acceptable salt or an in vivo hydrolysable ester thereof is described. The use of compounds of formula (I) in the production of an elevation of PDH activity in a warm-blooded animal such as a human being are also described. Pharmaceutical compositions, methods and processes for preparation of compounds of formula (I) are detailed. STR1

Selection, purification, characterisation, and cloning of a novel heat-stable stereo-specific amidase from Klebsiella oxytoca, and its application in the synthesis of enantiomerically pure (R)- and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acids and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide

We isolated, characterised, and cloned an enantio-specific amidase from Klebsiella oxytoca and used it to resolve (R,S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide, giving (R)3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide. The (S)-amide could then be hydrolysed chemically to (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid. The process can therefore be adapted to produce both (R)-and (S)-enantiomers of 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid, or (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide. The biocatalytic step is part of a combined chemical and biocatalytic route that starts from ethyl trifluoroacetoacetate. The products typically have a purity of greater than 98% and ee values of essentially 100% after isolation. The process has been used to produce 100-g amounts of the (S)-acid, and successfully scaled up to produce 100-kg amounts of the (R)-acid, with the biotransformation carried out at the 1500-L scale.