352-61-4 | 5,5,5-TRIFLUOROPENTAN-1-OL

CAS:352-61-4 | 5,5,5-TRIFLUOROPENTAN-1-OL,Description

Synthesis Analysis

The synthesis of fluorinated compounds, including structures similar to 5,5,5-Trifluoropentan-1-ol, often involves nucleophilic substitution reactions where fluorine atoms or fluorine-containing groups are introduced to the molecule. Notable methodologies include the use of 1,1-difluoro-1-alkenes as precursors in cyclization reactions, where the presence of fluorine atoms influences the reactivity and outcome of these processes (Ichikawa et al., 2002).

Molecular Structure Analysis

The molecular structure of fluorinated alcohols like 5,5,5-Trifluoropentan-1-ol is characterized by the strong electronegativity of fluorine, which affects the electron density distribution along the molecule. Fluorine atoms can induce unique electronic effects, leading to distinct molecular geometries and solid-state structures, as seen in various fluorinated compounds (Facchetti et al., 2004).

Chemical Reactions and Properties

Fluorinated compounds exhibit unique reactivity patterns due to the influence of the trifluoromethyl group. For instance, the presence of fluorine atoms in certain positions can facilitate nucleophilic 5-endo-trig cyclizations, which are otherwise disfavored processes. This reactivity is exploited in synthesizing heterocycles and carbocycles containing fluorinated units, demonstrating the significant impact of fluorine on chemical behavior (Ichikawa et al., 2008).

Physical Properties Analysis

The introduction of fluorine atoms into organic molecules dramatically influences their physical properties, including solubility, volatility, and stability. Fluorinated alcohols, for example, exhibit different solubility patterns in water and organic solvents compared to their non-fluorinated counterparts due to the hydrophobic nature of the fluorine atom and its effect on intermolecular interactions (Fioroni et al., 2003).

Chemical Properties Analysis

The chemical properties of 5,5,5-Trifluoropentan-1-ol, such as acidity, reactivity towards nucleophiles and electrophiles, and participation in various organic reactions, are distinctly influenced by the trifluoromethyl group. This group affects the electron density and polarization of the molecule, leading to unique reactivity patterns and the formation of stable intermediates in organic synthesis (Umemoto & Gotoh, 1987).

Scientific Research Applications

• Synthesis of Trifluoromethylated Pyrazoles : This compound is used in the synthesis of trifluoromethylated pyrazoles, which are significant in various chemical reactions (Lyga & Patera, 1990).
• Formation of 5,5,5-Trifluorolaevulic Acid : It is pivotal in the preparation, dehydration, and subsequent chemical reactions leading to the formation of 5,5,5-trifluorolaevulic acid and its derivatives (Brown, Burdon, Smith, & Tatlow, 1960).
• Catalytic Properties in Organic Chemistry : It exhibits properties useful as a catalyst in organic and organometallic chemistry, facilitating reactions such as hydrometallation, alkylations, and aldol-type reactions (Erker, 2005).
• Applications in Energetic Materials Design : The compound has potential applications in designing energetic materials like explosives (Dippold, Izsák, & Klapötke, 2013).
• Enhanced Stability in Coiled-Coil Peptides : When incorporated into coiled-coil peptides, it contributes to increased stability and enhanced thermal stability (Montclare, Son, Clark, Kumar, & Tirrell, 2009) .
• Palladium-Mediated Cyclization Reactions : This compound plays a role in palladium-mediated cyclization of 1,5-hexadien-3-ols, leading to the formation of cyclopentadienes (Zair, Santelli-Rouvier, & Santelli, 1991).
• Electroluminescent Device Applications : It is used in the synthesis of materials with high electron affinities, suitable for applications like electron injecting/hole blocking layers in LEDs (Fink, Frenz, Thelakkat, & Schmidt, 1997).
• Enantioselective Synthesis : It aids in the highly enantioselective synthesis of trifluoroalkanols using chiral ruthenium catalysts (Kuroki, Asada, Sakamaki, & Iseki, 2000).
• Fabrication of Organic Light-Emitting Diodes (OLEDs) : Pt(II) complexes involving this compound have been used in the fabrication of blue and white OLEDs (Liao et al., 2015).
• Synthesis of Fluoroindoles : It is instrumental in the synthesis of 2-fluoroindoles through silver-catalyzed vinylic C-F bond activation (Fujita et al., 2016).

Safety And Hazards

5,5,5-Trifluoropentan-1-ol is classified as an irritant. It is recommended to avoid dust formation, breathing mist, gas or vapors, and contact with skin and eyes. Use of personal protective equipment and chemical impermeable gloves is advised. In case of accidental release, it is recommended to avoid letting the chemical enter drains and to collect and arrange for appropriate disposal.

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