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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzothiazoles Benzothiazoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzothiazoles

Comprehensive Overview of 5-Methoxy-1,3-benzothiazole-2-carbaldehyde (CAS No. 854059-90-8): Properties, Applications, and Industry Insights

5-Methoxy-1,3-benzothiazole-2-carbaldehyde (CAS No. 854059-90-8) is a specialized organic compound gaining attention in pharmaceutical and agrochemical research due to its unique structural features. As a benzothiazole derivative, this compound combines a methoxy group at the 5-position with an aldehyde functionality at the 2-position, making it a versatile intermediate for synthesizing biologically active molecules. Recent studies highlight its potential as a precursor for antimicrobial agents and fluorescence probes, aligning with growing industry demands for novel therapeutic and diagnostic tools.

The molecular structure of 5-methoxy-1,3-benzothiazole-2-carbaldehyde features a heterocyclic benzothiazole core, which is known to enhance bioavailability and binding affinity in drug design. Researchers are particularly interested in its electron-rich aromatic system, as demonstrated by its UV-Vis absorption maxima around 320-350 nm, a property relevant to photocatalysis applications. With a molecular weight of 193.22 g/mol and purity standards typically exceeding 97% (HPLC), this compound meets stringent requirements for high-throughput screening in modern drug discovery pipelines.

Current market trends show increased searches for "benzothiazole aldehyde synthesis" and "methoxy benzothiazole applications," reflecting academic and industrial interest. The compound's aldehyde group enables diverse condensation reactions, particularly in developing Schiff base ligands for metal complexes with potential anticancer activity. Analytical techniques like LC-MS and NMR spectroscopy confirm its stability under standard storage conditions (2-8°C in amber vials), addressing common user queries about compound handling.

In material science, 854059-90-8 serves as a building block for organic semiconductors, with its extended π-conjugation system showing promise in OLED development. Patent analyses reveal growing IP activity around benzothiazole-based fluorophores, particularly for bioimaging sensors – a hot topic in nanotechnology forums. The compound's low cytotoxicity (confirmed by MTT assays) further supports its use in bioconjugation chemistry for targeted drug delivery systems.

Environmental considerations position 5-methoxy-1,3-benzothiazole-2-carbaldehyde as a greener alternative to heavy metal-containing catalysts in certain cross-coupling reactions. Its degradation profile, studied via HPLC-MS/MS, shows 90% breakdown within 28 days under simulated sunlight (OECD 301B), addressing sustainability concerns in chemical manufacturing. These attributes correlate with rising Google searches for "biodegradable heterocycles" and "eco-friendly synthetic intermediates."

Quality control protocols for CAS 854059-90-8 emphasize residual solvent analysis by GC and heavy metal testing (USP <231>), meeting GMP standards for pharmaceutical intermediates. The compound's crystallinity (verified by PXRD) and melting point range (142-145°C) provide critical specifications for process chemists optimizing scale-up production – a frequent discussion point in chemical engineering webinars.

Emerging applications include the development of COVID-19 protease inhibitors, where benzothiazole scaffolds show binding affinity to viral proteins. While 854059-90-8 itself isn't bioactive, its derivatives are being screened in virtual ligand docking studies, generating substantial academic literature. This connects to trending searches for "broad-spectrum antiviral compounds" and "pandemic preparedness chemistry."

From a commercial perspective, 5-methoxy-1,3-benzothiazole-2-carbaldehyde is available in various packaging configurations (1g to 1kg) with certificates of analysis including H-NMR, 13C-NMR, and HRMS data. Suppliers typically provide structure-activity relationship (SAR) guidance, assisting medicinal chemists in rational drug design – a service increasingly demanded in CRO (Contract Research Organization) workflows.

The compound's regioselectivity in electrophilic substitution reactions makes it valuable for creating structure-activity relationship libraries. Computational chemistry studies using DFT calculations predict favorable HOMO-LUMO gaps (≈3.8 eV), explaining its utility in organic electronics research. These technical aspects respond to frequent queries about "benzothiazole frontier orbitals" in computational chemistry forums.

Looking ahead, 5-methoxy-1,3-benzothiazole-2-carbaldehyde is poised to play a significant role in precision medicine development, particularly in theranostic applications combining therapy and diagnosis. Its structure-property relationships continue to be explored through advanced techniques like X-ray crystallography and time-resolved fluorescence spectroscopy, positioning CAS 854059-90-8 as a compound of enduring scientific and industrial relevance.

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