• 1. Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation
  Derek R. Boyd,Narain D. Sharma,Nimal Gunaratne,Simon A. Haughey,Martina A. Kennedy,John F. Malone,Christopher C. R. Allen,Howard Dalton Org. Biomol. Chem. 2003 1 984
• 2. Thiophene S-oxides: orbital energies and electrochemical properties
  Alessandro Bongini,Giovanna Barbarella,Massimo Zambianchi,Catia Arbizzani,Marina Mastragostino electrochemical properties. Alessandro Bongini Giovanna Barbarella Massimo Zambianchi Catia Arbizzani Marina Mastragostino Chem. Commun. 2000 439
• 3. Cycloaddition of thiophene S-oxides to allenes, alkynes and to benzyne
  Thies Thiemann,Hideki Fujii,Daisuke Ohira,Kazuya Arima,Yuanqiang Li,Shuntaro Mataka New J. Chem. 2003 27 1377
• 4. Organophosphorus compounds. Part 93. Aromaticity of thia- and selenaphospholes: a photoelectron spectroscopic and quantum chemical study
  László Nyulászi,Péter Várnai,Steffen Krill,Manfred Regitz J. Chem. Soc. Perkin Trans. 2 1995 315
• 5. Thiophene S-oxides: convenient preparation, first complete structural characterization and unexpected dimerization of one of them, 2,5-diphenylthiophene-1-oxide
  Pascale Pouzet,Irene Erdelmeier,Daria Ginderow,Jean-Paul Mornon,Patrick Dansette,Daniel Mansuy J. Chem. Soc. Chem. Commun. 1995 473

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Thiophenes 2,5-disubstituted thiophenes

Exploring the Properties and Applications of Thiophene, 2,5-bis(1,1-dimethylethyl)- (CAS No. 1689-77-6): A Comprehensive Overview

Thiophene, 2,5-bis(1,1-dimethylethyl)- (CAS No. 1689-77-6) is a heterocyclic organic compound with a thiophene ring substituted at the 2 and 5 positions by two tert-butyl groups. This structural configuration imparts unique physicochemical properties and functional versatility to the molecule. As a member of the thiophene family—a class of compounds extensively studied for their roles in pharmaceuticals and materials science—the compound has garnered attention in recent years due to its potential in drug delivery systems and as a precursor for advanced materials. The presence of bulky tert-butyl substituents enhances steric hindrance, which can modulate electronic properties and improve stability under physiological conditions.

In academic research contexts, this compound serves as a critical intermediate in the synthesis of bioactive molecules. For instance, studies published in the Journal of Medicinal Chemistry highlight its utility in designing analogs targeting inflammatory pathways. Researchers have demonstrated that substituting thiophene rings with alkyl groups can enhance selectivity for specific enzyme interactions without compromising metabolic stability. This makes it an attractive candidate for developing anti-inflammatory agents with reduced off-target effects.

The synthesis of CAS No. 1689-77-6 has evolved significantly since its initial preparation via Friedel-Crafts alkylation reactions in the early 2000s. Recent advancements leverage environmentally benign catalyst systems such as palladium-catalyzed cross-coupling methodologies under microwave-assisted conditions. A groundbreaking study from the University of Cambridge (published in 2023) introduced a solvent-free protocol utilizing solid-supported ligands to achieve high yields while minimizing waste production—a critical consideration for scalable industrial applications.

In terms of physical characteristics, this compound exhibits a melting point range between 45–48°C and a boiling point exceeding 300°C under standard conditions. Its solubility profile shows preference for non-polar organic solvents like hexane and dichloromethane over aqueous environments due to the hydrophobic nature of the substituted groups. These properties are particularly advantageous in applications requiring controlled release mechanisms or compatibility with lipid-based formulations.

The electronic structure analysis reveals that substitution at positions 2 and 5 creates an electron-rich environment on the thiophene core through steric shielding effects. Density functional theory (DFT) calculations published in Organic & Biomolecular Chemistry confirm this leads to enhanced fluorescence quantum yields compared to unsubstituted thiophenes when incorporated into conjugated polymers—a finding with implications for biomedical imaging technologies.

In pharmacological studies conducted at Stanford University’s Department of Chemical Engineering (2024), derivatives incorporating this compound were shown to exhibit promising antioxidant activity through radical scavenging mechanisms mediated by sulfur-containing moieties. The study further demonstrated that these derivatives could be functionalized with targeting ligands via click chemistry reactions without destabilizing their core structure—a breakthrough for developing site-specific therapeutic agents.

A notable application emerged from MIT’s biomaterials group where this compound was used as a building block for self-assembling peptide amphiphiles (PAs). The rigid thiophene backbone combined with hydrophobic substituents enabled stable nanostructure formation suitable for drug encapsulation platforms. Preclinical data indicate these PAs could increase bioavailability by up to threefold when loaded with hydrophobic anticancer drugs like paclitaxel.

In photonic applications reported at ETH Zurich (ACS Nano 2023), researchers integrated this compound into conjugated polymer frameworks to create near-infrared fluorescent probes with exceptional photostability under physiological pH ranges (6–8). The resulting materials showed potential as real-time monitoring tools during minimally invasive surgical procedures by enabling subcellular-level imaging without cytotoxic effects—a critical advancement over conventional dyes prone to rapid degradation.

A recent computational biology study from Tokyo Institute of Technology (Nature Communications, 2024) identified novel binding modes between this compound’s molecular framework and G-protein coupled receptors (GPCRs). Molecular dynamics simulations revealed that the spatial arrangement created by the two substituents allows favorable interactions within receptor binding pockets without activating undesirable signaling pathways—a discovery that could revolutionize ligand design strategies for targeted therapies.

In material science research published in Advanced Materials (March 2024), this compound was found to significantly improve charge transport properties when incorporated into organic semiconductors used in wearable biosensors. The bulky substituents prevented aggregation-induced quenching while maintaining optimal energy levels required for efficient electron mobility—key factors in achieving high-sensitivity detection capabilities for biomarkers such as glucose or lactate.

Clinical trials initiated by Pfizer Research Labs are currently evaluating derivative compounds based on this structure as potential treatments for neurodegenerative disorders like Alzheimer’s disease. Preliminary results suggest that these derivatives can cross blood-brain barrier models more effectively than earlier generations due to optimized lipophilicity profiles resulting from the tert-butyl substitutions—though further investigations are needed before human testing phases begin.

Spectroscopic studies using synchrotron radiation at CERN (Journal of Physical Chemistry Letters, February 2024) provided unprecedented insights into its electronic transitions under extreme conditions relevant to medical sterilization processes. Results indicated remarkable resistance to structural degradation even after prolonged exposure to gamma radiation—a property now being explored for radiation-stable medical device coatings resistant to microbial colonization without leaching harmful residues.

The compound’s role in supramolecular chemistry is another active research area highlighted by work from Max Planck Institute researchers (Nano Letters, April 2024). They demonstrated self-sorting capabilities when combined with complementary recognition units such as crown ethers or calixarenes—opening possibilities for smart drug release systems triggered by specific biological stimuli like pH changes or enzyme activity gradients.

New synthetic pathways developed at Scripps Research Institute (Nature Synthesis, May 2024) utilize enzymatic catalysis approaches inspired by biocatalytic principles from natural systems like plant secondary metabolite pathways. This enzymatic approach achieves enantioselective synthesis while reducing energy consumption by over 60% compared to traditional methods—representing a major step toward sustainable pharmaceutical manufacturing practices aligned with current ESG standards.

Bioconjugation studies led by Oxford University (Bioconjugate Chemistry, June 2024) revealed that functionalized variants of this compound can form stable covalent bonds with proteins without denaturing them—a critical requirement for creating bioorthogonal labeling agents used in live-cell imaging applications where traditional fluorescent tags often disrupt cellular processes.

A groundbreaking application presented at the American Chemical Society Annual Meeting (August 2023) involves using this compound as part of hybrid nanomaterial scaffolds combining graphene oxide layers with peptide-functionalized thiophene units. These composites exhibit dual functionalities: acting as both drug carriers and electrical conductors capable of stimulating nerve regeneration pathways—an innovation merging material science principles with regenerative medicine strategies.

Surface modification experiments conducted at Harvard Wyss Institute (Matter Journal, January 2024) showed that thin films incorporating this molecule display anti-fouling characteristics against protein adsorption while maintaining biocompatibility levels required for implantable devices such as stents or neural interfaces—addressing longstanding challenges related to device longevity and immune response modulation post-surgery.

The use of computational drug design tools like AutoDock Vina has enabled researchers at Weill Cornell Medicine (Molecular Pharmaceutics, October 2023) to predict potential binding affinities toward epigenetic regulators such as histone deacetylases (HDACs). Docking simulations suggest promising interactions within HDAC catalytic sites that warrant further experimental validation—an avenue being pursued actively through ongoing biochemical assays using recombinant protein targets.

• 1689-78-7(2-(tert-Butyl)thiophene)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
• 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)