44864-47-3

Basic information

• Product Name: (R)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID
• Synonyms: (R)-2-(TRIFLUOROMETHYL)-2-HYDROXYPROPIONIC ACID;(R)-(+)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID;(R)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID;(R)-3,3,3-TRIFLUORO-2-HYDROXYISOBUTYRIC ACID;(R)-2-HYDROXY-2-(TRIFLUOROMETHYL)PROPIONIC ACID;R-TFM-LA;(R)-3,3,3-Trifluoro-2-hydroxy-2-methylpropionic;(-)-3,3,3-Trifluoro-2-methyl-L-lactic acid
• CAS NO: 44864-47-3
• Molecular Formula: C₄H₅F₃O₃
• Molecular Weight: 158.08
• Product Categories: Carboxylic Acids (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry;Enantiomerically Pure Compounds;Various enantiomerically Pure Compounds
• Mol File: 44864-47-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 110 °C
• Boiling Point: 247.4±35.0℃ (760 Torr)
• Flash Point: 103.4±25.9℃
• Appearance: white powder
• Density: 1.532±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.0042mmHg at 25°C
• Refractive Index: 16.5 ° (C=5, H2O)
• Storage Temp.: Refrigerator
• PKA: 2.46±0.22(Predicted)
• Water Solubility: Soluble in water
• CAS DataBase Reference: (R)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID(44864-47-3)
• EPA Substance Registry System: (R)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID(44864-47-3)

Safety Data

• Hazard Codes: Xi
• Statements: 34
• Safety Statements: 26-36/37/39-24/25
• RIDADR: 3261
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 44864-47-3(Hazardous Substances Data)

Usage

Description

(R)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID is a chiral building block with the chemical properties of a white powder. It is an essential compound in the synthesis of various pharmaceuticals and other specialty chemicals due to its unique stereochemistry and functional groups.

Uses

Used in Pharmaceutical Industry:
(R)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID is used as a chiral building block for the development of new drugs with improved efficacy and selectivity. Its unique stereochemistry allows for the creation of enantiomerically pure compounds, which can exhibit different biological activities and reduce potential side effects.
Used in Chemical Synthesis:
(R)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID is used as a key intermediate in the synthesis of various specialty chemicals, including agrochemicals, fragrances, and other fine chemicals. Its versatile functional groups enable a wide range of chemical reactions, leading to the formation of diverse products with specific applications.
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InChI:InChI=1/C4H5F3O3/c1-3(10,2(8)9)4(5,6)7/h10H,1H3,(H,8,9)/t3-/m1/s1

Upstream product

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

Downstream Products

• 242139-87-3 (R)-N-[2-chloro-4-iodophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide 
• 242139-90-8 (R)-N-[2-fluoro-4-(phenylsulphanyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide 
• 242139-91-9 (R)-N-[2-chloro-4-(phenylsulphanyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide 
• 243982-46-9 (R)-N-(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 

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.