44864-47-3 | (R)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID

CAS:44864-47-3 | (R)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID,Description

(R)-3,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acid is a chiral compound that has potential applications as a building block in organic synthesis due to its trifluoromethyl group and chiral center. The presence of both a hydroxyl and a carboxylic acid functional group makes it a versatile intermediate for various chemical transformations.

Synthesis Analysis

The synthesis of enantiomerically pure (R)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid can be achieved through biocatalytic methods. Shinella sp. R-6 has been identified as a microorganism capable of R-selective hydrolysis activity, which can be used to prepare the R-enantiomer of the acid from its corresponding amide. This method provides an efficient route to obtain the desired enantiomer using whole-cell biocatalysis.

Molecular Structure Analysis

The molecular structure of (R)-3,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acid is characterized by the presence of a trifluoromethyl group, which imparts unique electronic and steric properties to the molecule. The chiral center at the carbon bearing the hydroxyl group is responsible for its optical activity. The exact configuration of the chiral center can be determined through X-ray crystallography, as demonstrated in the resolution of racemic mixtures using chiral diols.

Chemical Reactions Analysis

The chemical reactivity of (R)-3,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acid is influenced by the electron-withdrawing trifluoromethyl group, which can affect the acidity of the carboxylic acid and the reactivity of the hydroxyl group. This compound can undergo various chemical reactions typical of carboxylic acids and alcohols, such as esterification, amidation, and oxidation. The enantiopure acid can serve as a precursor for further chiral synthesis, as seen in the production of chiral hydroxyalkanoic acids and their esters.

Physical and Chemical Properties Analysis

The physical properties of (R)-3,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acid, such as melting point, boiling point, and solubility, are influenced by the presence of both hydrophilic (hydroxyl and carboxyl groups) and hydrophobic (trifluoromethyl group) elements in the molecule. The chemical properties, including acidity and reactivity, are also affected by these functional groups. The compound's enantiomeric purity can be assessed using chiral gas chromatography, ensuring its suitability for use in enantioselective synthesis.

Scientific Research Applications

1. Biocatalytic Synthesis and Enantioselective Hydrolysis (R)-3,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acid has been explored in the context of biocatalytic synthesis. Microorganisms capable of enantioselectively hydrolyzing related compounds have been isolated for efficient preparation of both enantiomers of this acid (Fuhshuku et al., 2014). Similarly, Burkholderia phytofirmans and a novel amidase (Bp-Ami) have been used for the synthesis of the optically pure (R)-enantiomer (Wu et al., 2017).

2. Substrate Specificity in Amidases The substrate specificity of certain amidases for this compound has been a topic of research. Klebsiella oxytoca, for instance, has shown the ability to accept derivatives of this compound as substrates, highlighting a new synthetic route for its enantiomers (Shaw & Naughton, 2004).

3. Synthesis Methodologies Advancements in synthesis methodologies involving (R)-3,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acid have been made. For example, a convenient one-pot synthesis method for its derivatives was developed, emphasizing the importance of this compound in creating enantiopure derivatives (Li et al., 2013).

4. Crystal Structure Analysis The crystal structure of racemic versions of this compound has been analyzed to understand its molecular properties better. This analysis provides insights into the molecular arrangement and potential applications in various fields (Gerber & Betz, 2013).

Safety And Hazards

This involves understanding the safety measures needed to handle the compound and the possible hazards it could pose. Material Safety Data Sheets (MSDS) are often referred to for this information.

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