359-41-1 | 2-(Trifluoromethyl)oxirane

CAS:359-41-1 | 2-(Trifluoromethyl)oxirane ,Description

2-(Trifluoromethyl)oxirane (TFMO) is a small organic molecule with a variety of applications in scientific research, medicine, and industry. It is a versatile compound, with properties that make it useful in a wide range of applications. 
 

Scientific Research Applications

Synthesis and Chemical Transformations

2-(Trifluoromethyl)oxirane has been utilized in various synthesis processes. For instance, enantiomerically pure trifluorolactic acids were converted into (R)- and (S)-(trifluoromethyl)oxirane, offering potential for further synthetic applications (von dem Bussche-Hünnefeld, Cescato, & Seebach, 1992) . Similarly, the paper by Petrov (2002) describes the ring-opening reactions of 2,2-bis(trifluoromethyl)oxirane, leading to the formation of tertiary alcohols, showcasing its versatility in chemical transformations (Petrov, 2002).

Molecular Structure and Properties

Investigations into the molecular structure of 2,2-bis(trifluoromethyl)oxirane revealed insights into its configuration. Cooke and Minei (2012) found that the CF3 groups in this compound are slightly staggered but have a low barrier to an eclipsed configuration, indicating interesting molecular dynamics (Cooke & Minei, 2012).

Green Chemistry Applications

The compound's use in green chemistry was highlighted by Li et al. (2010), who demonstrated its utility in the regio- and diastereoselective ring-opening, contributing to the synthesis of potent inhibitors without the need for rare earth metal salts (Li et al., 2010) .

Interaction with Other Chemicals

Research by Alonso et al. (2004) on the oxirane-trifluoromethane dimer revealed weak C-H...O and C-H...F-C hydrogen bonds, providing insights into the interaction potential of 2-(trifluoromethyl)oxirane with other molecules (Alonso et al., 2004).

Analytical Chemistry

In analytical chemistry, (S)-2-[(R)-Fluoro(phenyl)methyl]oxirane has been used as a reagent for determining the enantiomeric excess of α-chiral amines, showing its utility in chiral resolution processes (Rodríguez-Escrich et al., 2005) .

Pharmaceutical and Agrochemical Research

The compound's role in creating stereogenic trifluoromethyl-substituted carbon centers, important in pharmaceutical and agrochemical discovery, was explored by Nandakumar et al. (2019). Their work showed how lithiation-borylation reactions of 2-trifluoromethyl oxirane yield versatile trifluoromethyl-substituted α-tertiary boronic esters, which are critical in synthesizing complex molecules (Nandakumar et al., 2019).

Chemistry of Oxiranes

The study by Shimizu et al. (2008) demonstrated a facile route to 2-trifluoromethyl-substituted 4,5-dihydrooxepins, involving the stereoselective preparation and Cope rearrangement of 2-trifluoromethyl-cis-2,3-bis(alkenyl)oxiranes. This highlights the compound's utility in synthesizing oxacycles, which are significant in organic synthesis (Shimizu et al., 2008).

Reaction with Alcohols

Petrov's research (2004) showed that 2,2-bis(trifluoromethyl)oxirane reacts with various alcohols under phase transfer catalysis, leading to the production of tertiary alcohols. This demonstrates the compound's reactivity and potential for creating diverse chemical structures (Petrov, 2004).

Hypoglycemic Activity

In a study on the hypoglycemic activity of phenylalkyloxiranecarboxylic acid derivatives, Eistetter and Wolf (1982) found that derivatives of 2-(phenylalkyl)oxirane-2-carboxylic acids exhibited significant blood glucose-lowering activities in fasted rats, indicating potential therapeutic applications (Eistetter & Wolf, 1982).

Friedel-Crafts Alkylations

Prakash et al. (2007) described the use of triflic acid-catalyzed Friedel-Crafts alkylation of aromatics with mono- and bis(trifluoromethyl)oxiranes. This process highlights the compound's role in facilitating regioselective ring openings and subsequent alkylations, crucial in organic synthesis (Prakash et al., 2007).

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