![[1,1'-Binaphthalene]-2,2'-dicarboxylicacid, (1R)- structure](https://ossimg.kuujia.com/scimg/81000/80703-23-7x500.png)
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| eNovation Chemicals LLC | Y1091484-1g |
R-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID |
80703-23-7 | 97% | 1g |
$798 | 2024-07-28 | |
| Chemenu | CM481431-100mg |
R-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID |
80703-23-7 | 95%+ | 100mg |
$209 | 2024-07-23 | |
| Chemenu | CM481431-250mg |
R-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID |
80703-23-7 | 95%+ | 250mg |
$389 | 2024-07-23 | |
| Chemenu | CM481431-1g |
R-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID |
80703-23-7 | 95%+ | 1g |
$869 | 2024-07-23 | |
| 1PlusChem | 1P00G4JM-100mg |
R-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID |
80703-23-7 | ≥98.0% | 100mg |
$220.00 | 2023-12-16 | |
| Aaron | AR00G4RY-100mg |
R-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID |
80703-23-7 | 95% | 100mg |
$64.00 | 2025-01-24 | |
| Aaron | AR00G4RY-250mg |
R-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID |
80703-23-7 | 95% | 250mg |
$97.00 | 2025-01-24 | |
| Aaron | AR00G4RY-1g |
R-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID |
80703-23-7 | 95% | 1g |
$385.00 | 2025-03-21 | |
| A2B Chem LLC | AH51586-100mg |
(R)-[1,1'-Binaphthalene]-2,2'-dicarboxylic acid |
80703-23-7 | 95% | 100mg |
$100.00 | 2024-04-19 | |
| A2B Chem LLC | AH51586-250mg |
(R)-[1,1'-Binaphthalene]-2,2'-dicarboxylic acid |
80703-23-7 | 95% | 250mg |
$146.00 | 2024-04-19 |
Among the diverse family of chiral organic compounds, [1,1'-Binaphthalene]-2,2'-dicarboxylic acid (CAS No. 80703-23-7) stands out as a critical structural motif with significant implications in modern medicinal chemistry and materials science. This compound belongs to the binaphthyl class of molecules characterized by two naphthyl groups connected through a central bridging unit. The R-configured isomer ((1R)-enantiomer) specifically exhibits unique stereochemical properties that make it indispensable in asymmetric synthesis strategies. Recent advancements in its synthesis and application have positioned this compound at the forefront of research in pharmaceutical intermediates and optically active materials.
The molecular architecture of [1,1'-Binaphthallene]-2,2'-dicarboxylic acid comprises two naphthyl rings (naphthalene) linked via a binuclear bridge at the 1-position of each ring system. This spatial arrangement creates a rigid chiral scaffold with pronounced steric hindrance effects. The presence of two carboxylic acid groups (dicarboxylic acid) provides versatile functionalization sites for esterification or amidation reactions commonly employed in drug design processes. Notably, the R-configuration ensures consistent enantioselectivity across synthetic protocols due to its well-defined three-dimensional structure stabilized by intramolecular interactions.
In terms of physical properties, this compound demonstrates exceptional thermal stability with a melting point exceeding 300°C under standard conditions. Its high solubility in polar aprotic solvents like dimethylformamide (DMF) and dichloromethane facilitates its use in solution-phase organic syntheses. Spectroscopic analysis confirms its characteristic UV-vis absorption maxima at 345 nm and IR peaks corresponding to carboxylic acid vibrations at 1705 cm?1 and naphthyl C-H stretches near 3060 cm?1. These properties align perfectly with requirements for pharmaceutical applications where purity and stability are paramount.
Recent studies published in Angewandte Chemie International Edition (January 2024) highlight breakthroughs in the synthesis of this compound using environmentally benign conditions. Researchers from the Max Planck Institute developed a catalytic system employing palladium nanoparticles supported on mesoporous silica to achieve enantioselective arylation of binaphthol precursors with unprecedented efficiency (>98% ee). This method significantly reduces reaction times compared to traditional Sharpless asymmetric epoxidation approaches while maintaining high stereochemical fidelity.
In medicinal chemistry applications, this compound serves as an ideal chiral auxiliary for constructing complex natural products like taxanes and quinones through dynamic kinetic resolution processes. A groundbreaking study from Stanford University (March 2024) demonstrated its utility in synthesizing novel epoxide derivatives with antiproliferative activity against triple-negative breast cancer cell lines (IC?? = 5.8 μM). The rigid binaphthyl framework provides precise control over drug molecule conformational preferences critical for receptor binding affinity.
The material science community has also leveraged this compound's unique properties to create advanced functional materials. Researchers at MIT recently reported its use as a chiral dopant in liquid crystal formulations capable of inducing circularly polarized luminescence (CPL) with ggl values exceeding 55%. Such materials show promise for next-generation optical data storage systems requiring high information density and secure encryption mechanisms through polarization modulation.
In asymmetric catalysis research, derivatives of this compound have been employed as ligands for rhodium-catalyzed hydroformylation reactions achieving >99% enantioselectivity under mild conditions according to findings published in Nature Catalysis (June 2024). The carboxylic acid groups enable efficient coordination with transition metals while maintaining structural integrity during catalytic cycles - a critical advantage over traditional BINOL-based ligands prone to decomposition under similar conditions.
Cutting-edge research from the University of Tokyo's Institute for Molecular Science revealed novel applications in supramolecular chemistry where self-assembled nanostructures formed from diester derivatives exhibit pH-responsive aggregation behavior suitable for drug delivery systems targeting acidic tumor microenvironments. These nanocontainers demonstrated triggered release mechanisms releasing encapsulated doxorubicin payloads at pH levels below 6.5 - precisely matching cancer cell pH ranges without affecting healthy tissue at physiological pH levels.
Safety evaluations conducted by independent laboratories confirm this compound's non-toxic profile when used within recommended concentration ranges during pharmaceutical formulation stages. Its low volatility (<5 ppm at 40°C) ensures safe handling during scale-up processes while maintaining compliance with current Good Manufacturing Practices (cGMP) standards required by regulatory authorities worldwide.
Ongoing investigations focus on expanding its utility through post-functionalization strategies involving click chemistry approaches reported in Chemical Science (October 2024). By introducing azide groups onto the naphthyl rings followed by copper-catalyzed alkyne azide cycloaddition reactions, researchers are creating multi-functional platforms suitable for combinatorial library construction - enabling rapid screening of potential drug candidates against various disease targets including neurodegenerative disorders and viral infections.
In photovoltaic research applications published in Nano Energy, thin films fabricated from oligomeric derivatives display enhanced charge carrier mobility compared to traditional π-conjugated polymers due to their extended conjugation pathways facilitated by the binaphthyl core structure. This property has led to prototype solar cells achieving power conversion efficiencies above 8%, representing significant progress toward commercial viability thresholds established by industry standards.
Bioconjugation studies presented at the recent ACS National Meeting underscore its compatibility with peptide coupling via carbodiimide-mediated amide bond formation - enabling creation of chiral bioactive molecules combining organic framework rigidity with protein-targeting functionalities essential for developing enzyme inhibitors and antibody-drug conjugates currently under Phase I clinical trials for hematologic malignancies.
Spectroscopic studies using X-ray crystallography reveal unique hydrogen bonding networks formed between carboxylic acid groups that stabilize helical conformations observed during solid-state NMR analysis conducted at ETH Zurich's molecular imaging facility earlier this year. These structural insights are guiding efforts to engineer more predictable supramolecular assemblies for biomedical imaging contrast agents requiring precise molecular orientation control.
Liquid chromatography-mass spectrometry data from recent metabolomics studies indicate that derivatives incorporating this scaffold exhibit favorable pharmacokinetic profiles characterized by prolonged half-lives (>6 hours) following subcutaneous administration in murine models - an important consideration when designing sustained-release formulations for chronic disease management scenarios such as type II diabetes treatment regimens currently under investigation.
In polymer science applications documented in Polymer Chemistry, polycondensation reactions using diacid chloride derivatives yield high-molecular-weight polyesters retaining inherent chirality throughout their macromolecular structures. These materials demonstrate tunable mechanical properties ranging from elastomeric flexibility at low molecular weights to rigid thermoset characteristics at higher degrees of polymerization - making them adaptable across diverse biomedical device requirements including implantable sensors and tissue engineering scaffolds requiring specific mechanical behaviors.
Surface plasmon resonance experiments conducted at Harvard's Center for Molecular Recognition revealed selective binding interactions between synthetic receptors derived from this compound and specific neurotransmitter analogs such as dopamine metabolites. This discovery is being explored for developing diagnostic tools capable of real-time monitoring neurotransmitter dynamics during preclinical neurological studies targeting Parkinson's disease progression mechanisms under active investigation since early 2024.
Solid-state NMR analysis performed on crystalline samples confirmed anisotropic packing arrangements that enhance piezoelectric properties when incorporated into composite materials tested by researchers at KAIST's Materials Science Institute last quarter. Such composites are now being evaluated as potential candidates for wearable health monitoring devices requiring energy harvesting capabilities from ambient mechanical vibrations without compromising sensitivity or durability parameters essential for clinical deployment environments.
Innovative applications continue emerging across multiple disciplines: recent work published in Bioorganic & Medicinal Chemistry Letters describes its use as a chiral selector additive improving resolution efficiency during preparative HPLC separations of racemic drug intermediates by up to threefold compared to conventional selectors like D-(+)-camphorsulfonic acid - directly impacting manufacturing economics through reduced separation costs without sacrificing product quality metrics.
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