125995-00-8

Basic information

• Product Name: (S)-(-)-3,3,3-TRIFLUORO-2-HYDROXYPROPANOIC ACID
• Synonyms: (S)-(-)-TRIFLUOROLACTIC ACID;S-TF-LA;(S)-(-)-3,3,3-TRIFLUORO-2-HYDROXYPROPANOIC ACID;(S)-(-)-3,3,3-TRIFLUOROLACTIC ACID;(S)-2-Hydroxy-3,3,3-trifluoropropionic acid;(S)-(-)-3,3,3-TRIFLUORO-2-HYDROXYPROPANOIC ACID (98% EE);3,3,3-Trifluoro-L-lactic acid;(2S)-2-Hydroxy-3,3,3-trifluoropropanoic acid
• CAS NO: 125995-00-8
• Molecular Formula: C₃H₃F₃O₃
• Molecular Weight: 144.05
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 125995-00-8.mol

Chemical Properties

• Melting Point: 72-76 °C(lit.)
• Boiling Point: 256.4 °C at 760 mmHg
• Flash Point: 108.9 °C
• Appearance: /
• Density: 1.445 g/cm³
• Vapor Pressure: 0.00231mmHg at 25°C
• Refractive Index: 1.365
• Storage Temp.: -20°C Freezer
• Solubility: Methanol
• PKA: 2.29±0.11(Predicted)
• Sensitive: Hygroscopic
• CAS DataBase Reference: (S)-(-)-3,3,3-TRIFLUORO-2-HYDROXYPROPANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-3,3,3-TRIFLUORO-2-HYDROXYPROPANOIC ACID(125995-00-8)
• EPA Substance Registry System: (S)-(-)-3,3,3-TRIFLUORO-2-HYDROXYPROPANOIC ACID(125995-00-8)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36-45
• RIDADR: UN 1759 8/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 125995-00-8(Hazardous Substances Data)

Usage

Uses

Used in Chiral Derivatization:
(S)-(-)-3,3,3-TRIFLUORO-2-HYDROXYPROPANOIC ACID is used as a chiral derivatizing agent for alcohols, particularly in the determination of enantiomeric purity of chiral secondary alcohols. This application is crucial in the field of stereochemistry and pharmaceuticals, where the purity and composition of chiral compounds are of great importance.
Used in Synthesis of Chiral Compounds:
In the chemical industry, (S)-(-)-3,3,3-TRIFLUORO-2-HYDROXYPROPANOIC ACID serves as a reactant for synthesizing various chiral compounds, such as (S,S) Double-headed bis(trifluorolactate)s with polymethylene chains. These are produced through esterification reactions with α,ω-alkanediols, contributing to the development of new chiral materials and molecules with potential applications in various fields.
Additionally, it is utilized in the synthesis of Chiral 1,1,1-trifluoromethyl-2-alkanols, which are valuable intermediates in the production of pharmaceuticals, agrochemicals, and other specialty chemicals. The unique properties of the trifluoromethyl group in these compounds make them attractive for various applications, including enhancing the biological activity and stability of the final products.

InChI:InChI=1/C3H3F3O3/c4-3(5,6)1(7)2(8)9/h1,7H,(H,8,9)/t1-/m0/s1

Upstream product

• 94726-00-8 ethyl 3,3,3-trifluoro-2-hydroxypropanoate 
• 130025-34-2 (S)-2-trifluoromethyl-oxirane 

Downstream Products

• 245363-09-1 1-phenylethyl 3,3,3-trifluoro-2-hydroxypropionate 
• 1225204-19-2 N-phenyl-3,3,3-trifluorolactyl amide 
• 125969-76-8 N-benzyl-3,3,3-trifluorolactyl amide 

Relevant articles and documents

Temperature-dependent penetration of argon molecules into ultramicroporous tunnel of a fluoroorganic molecular crystal with alteration of its unit cell size

A molecular crystal of octamethylene (S,S)-bis(2-hydroxy-3,3,3- trifluoropropanoate) with an ultramicroporous tunnel (Φ = 2.5-2.8 A) starts to adsorb argon (Φ = 3.6 A) at 150-140 K with 7% increase of the one direction of the orthorhombic unit cell. The alteration of the unit cell size indicates the penetration of argon into the tunnel and the soft nature of the microporous molecular crystal. Copyright

Simple Access to (R)- and (S)-3,3,3-Trifluorolactic Acid and to (R)- and (S)-(Trifluoromethyl)oxirane

Ethyl trifluoropyruvate (from hexafluoropropylene oxide) is reduced by NaBH4 to rac-trifluorolactic acid which is resolved on a 100-g scale by salt formation with (R,R)- and (S,S)-2-amino-1-phenyl-1,3-propanediol (readily available intermediates of industrial chloroamphenicol synthesis).The enantiomerically pure trifluorolactic acids (>99percent ee by GC analysis on cyclodextrin columns) are converted into (R)- and (S)-(trifluoromethyl)oxirane in an overall yield of 73percent by the following steps: esterification, THP protection of the OH group, LAH reduction and mesylation to the 2-THP-protected mesylate of 3,3,3-trifluoro-1,2-propanediol, and one-pot deprotection (Dowex 50) and cyclization (NaOCH2CH2OH) in ethylene glycol.The enantiomeric purity of the oxirane (b.p. 39 deg C, isolated on a 10-g scale) was determined by GC to be >99percent.Possible synthetic targets are mentioned which should be accessible in enantiomerically pure form from the (trifluoromethyl)oxirane described here. Key Words: Resolution by crystallization of diastereomeric salts / Perfluoropropylene oxide / Trifluoropyruvate / Capillary GC determination of ratios of enantiomers / Cyclodextrine-derived GC columns / Determination of the sense of chirality by chemical correlation / pKs of 3,3,3-trifluoro-2-hydroxypropanoic and 4,4,4-trifluoro-3-hydroxybutanoic acid