175205-09-1 | 5-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]TETRAZOLE

CAS:175205-09-1 | 5-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]TETRAZOLE,Description

Synthesis Analysis

The synthesis of tetrazole derivatives, including those substituted with trifluoromethyl groups, typically involves cyclization reactions of nitriles or the interaction of azides with nitriles under specific conditions. One method involves the oxidative coupling of 5-aminotetrazoles, leading to bis(tetrazol-5-yl)diazenes, which can be further manipulated to introduce trifluoromethyl groups (Serebryanskaya et al., 2010 ). Another approach might involve the use of sulfur tetrafluoride to transform carboxylic groups into trifluoromethyl groups in a pyrazole core, as mentioned in studies focused on pyrazoles (Gerus et al., 2012).

Molecular Structure Analysis

The molecular structure of 5-[3,5-bis(trifluoromethyl)phenyl]-2H-tetrazole and its derivatives can be elucidated using various spectroscopic techniques such as NMR, IR, and particularly X-ray crystallography. These methods provide detailed insights into the arrangement of atoms, the geometry of the molecule, and the presence of intramolecular or intermolecular interactions, crucial for understanding the compound's reactivity and properties (Al-Hourani et al., 2015).

Chemical Reactions and Properties

Tetrazole derivatives, including those with trifluoromethyl substituents, participate in various chemical reactions, reflecting their potential utility in synthesizing complex molecules. The reactivity can be influenced by the electronic effects of the trifluoromethyl groups, which can affect the nucleophilicity and electrophilicity of the tetrazole ring. The literature discusses various coordination chemistries and the ability of tetrazoles to act as ligands, forming complexes with different metals, which impacts their chemical properties and potential applications (Ouellette et al., 2011).

Physical Properties Analysis

The physical properties of 5-[3,5-bis(trifluoromethyl)phenyl]-2H-tetrazole, such as solubility, melting point, and stability, are significantly influenced by the trifluoromethyl groups. These groups increase the compound's hydrophobicity, potentially affecting its solubility in organic solvents and water. The stability of the compound, both thermal and chemical, is also a crucial aspect, as it determines the compound's suitability for various applications (Haiges et al., 2013).

Chemical Properties Analysis

The chemical properties of 5-[3,5-bis(trifluoromethyl)phenyl]-2H-tetrazole, such as acidity, basicity, and reactivity towards electrophiles or nucleophiles, are pivotal in its applications. The presence of electronegative trifluoromethyl groups adjacent to the tetrazole ring can affect the electron density of the nitrogen atoms in the ring, potentially altering its reactivity patterns. Such properties are crucial for the development of pharmaceuticals and materials (Nishida et al., 1984).

Scientific Research Applications

• Coordination Chemistry : A study focused on synthesizing fluorinated 5-aryl-1H-tetrazoles, including (3,5-bis(trifluoromethyl)phenyl)tetrazole (BTFTH). The research found that BTFTH could be satisfactorily synthesized using several methods. A Cu complex of BTFTH was fully characterized, suggesting negligible superexchange between Cu^2+ ions (Gerhards et al., 2015).
• Julia-Kocienski Olefination : The use of 3,5-bis(trifluoromethyl)phenyl (BTFP) sulfones in the Julia-Kocienski olefination reaction with carbonyl compounds was examined. This method was employed for high-yielding and stereoselective synthesis of various compounds, including methoxylated stilbenes (Alonso et al., 2005).
• Antimicrobial Activity : A study synthesized a series of novel compounds including 2-[3,5-bis(trifluoromethyl)phenyl]-4-(substitutedphenyl)-1,4-dihydropyrimido[1,2-a]benzimidazole, evaluating their antibacterial and antifungal activity. This highlights potential pharmaceutical applications (Vora & Vyas, 2019).
• Solvent-extraction of Cations : Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (TFPB) was identified as a highly lipophilic, water-insoluble, acid- and oxidant-resistant agent, useful in the solvent-extraction of cations (Nishida et al., 1984).
• Tetrazolate-Bridged Coordination Framework : Another study focused on synthesizing a tetrazolate-bridged coordination framework, demonstrating the versatility of these compounds in material chemistry (Tao et al., 2004).

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