24435-45-8

Basic information

• Product Name: (S)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID
• Synonyms: (S)-(-)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID;(S)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID;(S)-3,3,3-TRIFLUORO-2-HYDROXYISOBUTYRIC ACID;(S)-2-(TRIFLUOROMETHYL)-2-HYDROXYPROPIONIC ACID;(S)-2-HYDROXY-2-(TRIFLUOROMETHYL)PROPIONIC ACID;S-TFM-LA;(S)-2-Hydroxy-2-trifluoro-oro-methylpropionic acid;(S)-3,3,3-Trifluoro-2-hydroxy-2-methylpropionic
• CAS NO: 24435-45-8
• Molecular Formula: C₄H₅F₃O₃
• Molecular Weight: 158.08
• Product Categories: Carboxylic Acids (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry
• Mol File: 24435-45-8.mol

Chemical Properties

• Melting Point: 110 °C
• Boiling Point: 60-64°C 20mm
• Flash Point: 103.4±25.9℃
• Appearance: /
• 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: (S)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID(24435-45-8)
• EPA Substance Registry System: (S)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID(24435-45-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3261 8/PG III
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 24435-45-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Biotechnology Industries:
(S)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID is used as a building block for the synthesis of various drugs and pharmaceutical intermediates, contributing to the development of new medications and therapies.
Used in Organic Chemistry Reactions:
(S)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID serves as a reagent in organic chemistry reactions, facilitating the synthesis of complex organic compounds and aiding in research and development.
Used in Agrochemical and Specialty Chemical Industries:
(S)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID is utilized as a component in the synthesis of agrochemicals and specialty chemicals, enhancing the effectiveness and properties of these products.
Used in the Production of Polymer Additives:
(S)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID is used as a key ingredient in the production of polymer additives, improving the performance and characteristics of polymer materials.
Used in the Production of Surfactants and Coatings:
(S)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID is employed in the synthesis of surfactants and coatings, contributing to the development of innovative and high-performance products in these industries.

InChI:InChI=1/C4H5F3O3/c1-3(10,2(8)9)4(5,6)7/h10H,1H3,(H,8,9)/t3-/m0/s1

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 
• 1425924-49-7 (S)-1,1,1-trifluoro-2-methyl-3-oxopropan-2-yl acetate 
• 857934-67-9 C₁₃H₁₆F₃NO₂ 
• 693287-31-9 (S)-2,3-epoxy-2-(trifluoromethyl)propionic acid 
• 693287-30-8 (R)-2,3-epoxy-2-(trifluoromethyl)propionic acid 

Downstream Products

• 243982-42-5 N-cyclohexyl-3,3,3-trifluoro-2-hydroxy-2-methyl-propionamide 
• 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 
• 329901-37-3 (R)-N-(4-[Anilinosulphonyl]-2,5-dimethoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide 
• 329901-38-4 (R)-N-(2,5-Dimethoxy-4-[dimethylaminosulphonyl]phenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide 
• 329926-82-1 (R)-N-(2-methyl-3-fluoro-4-iodophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide 
• 329794-58-3 (R)-[5-(4-methylsulphanylphenylsulphanyl)-1-(3,3,3-trifluoro-2-hydroxy-2-methylpropionyl)indoline] 
• 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 

Relevant articles and documents

Synthesis of optically pure 2-trifluoromethyl lactic acid by asymmetric hydroformylation

By utilizing Rh catalysts ligated by the P-chirogenic ligands QuinoxP* and DuanPhos, 3,3,3-trifluoroprop-1-en-2-yl acetate could be hydroformylated and subsequently oxidized to yield enantiomerically pure 2-trifluoromethyllactic acid.

A novel S-enantioselective amidase acting on 3,3,3-trifluoro-2-hydroxy-2-methylpropanamide from Arthrobacter sp. S-2

A novel S-enantioselective amidase acting on 3,3,3-trifluoro-2-hydroxy-2-methylpropanamide was purified from Arthrobacter sp. S-2. The enzyme acted S-enantioselectively on 3,3,3-trifluoro-2-hydroxy-2-methylpropanamide to yield (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid. Based on the N-terminal amino acid sequence of this amidase, the gene coding S-amidase was cloned from the genomic DNA of Arthrobacter sp. S-2 and expressed in an Escherichia coli host. The recombinant S-amidase was purified and characterized. Furthermore, the purified recombinant S-amidase with the C-His6-tag, which was expressed in E. coli as the C-His6-tag fusion protein, was used in the kinetic resolution of (±)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide to obtain (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid and (R)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide.

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.

Chirality-dependent sublimation of α-(trifluoromethyl)-lactic acid: Relative vapor pressures of racemic, eutectic, and enantiomerically pure forms, and vibrational spectroscopy of isolated (S,S) and (S,R) dimers

A mass-spectrometric determination of the sublimation pressure diagram of α-(trifluoromethyl)-lactic acid as a function of its enantiomeric composition at 293 K shows that the racemic crystals have a 38 ± 15 % higher volatility than the enantiomerically p

METHOD FOR PRODUCING OPTICALLY ACTIVE 3,3,3-TRIFLUORO-2-HYDROXYPROPIONIC ACID DERIVATIVE

PROBLEM TO BE SOLVED: To provide a method for industrially producing an optically active 3,3,3-trifluoro-2-hydroxypropionic acid derivative as an important intermediate for pharmaceuticals and agrochemicals. SOLUTION: The method comprises the following pr

Optically active fluorine-containing compounds and processes for their production

An optically active fluorine-containing compound represented by the following formula (1) or (2) wherein A is an oxygen atom, a sulfur atom or an NH group, and R1 selected from a variety of organic group, is used in the preparation of (S)- or (R)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid.

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

Benzenesulfonamide-derivatives and their use as medicaments

Compounds of formula (I), pharmaceutically acceptable salts or in vivo hydrolysable esters thereof, wherein: Ring X is phenyl or a six membered heteroaryl ring containing one or two ring nitrogens where said nitrogens are optionally oxidised to form the N

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.

Process for producing optically active 3,3,3-Trifluoro-2-Hydroxy-2-Methylpropionic acid, and salt thereof

There are disclosed are a diastereomer salt of formula (1): a process for producing the same, a process for producing optically active 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid of formula (2′): a novel optically active amine compound of formula (4): a novel optically active amine compound of formula (8): an imine compound of formula (7) or (11):