Cas no 325731-49-5 (6-(Difluoromethyl)sulfanyl-1,3-benzothiazol-2-amine)

6-(Difluoromethyl)sulfanyl-1,3-benzothiazol-2-amine is a fluorinated benzothiazole derivative with potential applications in agrochemical and pharmaceutical research. The difluoromethylthio (-SCF?H) substituent enhances its reactivity and metabolic stability, making it a valuable intermediate for the synthesis of biologically active compounds. The benzothiazole core contributes to its versatility in heterocyclic chemistry, while the amine group at the 2-position allows for further functionalization. This compound may exhibit improved lipophilicity and bioavailability compared to non-fluorinated analogs, offering advantages in the design of novel pesticides or therapeutic agents. Its structural features suggest utility in developing inhibitors or probes targeting sulfur-dependent enzymatic processes.
6-(Difluoromethyl)sulfanyl-1,3-benzothiazol-2-amine structure
325731-49-5 structure
Product Name:6-(Difluoromethyl)sulfanyl-1,3-benzothiazol-2-amine
CAS No:325731-49-5
MF:C8H6F2N2S2
MW:232.273445606232
CID:3105029
PubChem ID:2307352
Update Time:2025-10-31

6-(Difluoromethyl)sulfanyl-1,3-benzothiazol-2-amine Chemical and Physical Properties

Names and Identifiers

    • 6-Difluoromethylsulfanyl-benzothiazol-2-ylamine
    • 6-((difluoromethyl)sulfanyl)-1,3-benzothiazol-2-amine
    • HMS1769J17
    • MFCD02696567
    • AKOS000115538
    • ISUPFQHWEVPYBU-UHFFFAOYSA-N
    • 6-[(difluoromethyl)sulfanyl]-1,3-benzothiazol-2-amine
    • SR-01000026873
    • 325731-49-5
    • SCHEMBL21709931
    • CS-0218856
    • F3135-0046
    • SR-01000026873-1
    • G44779
    • 853-099-5
    • EN300-02278
    • Z56772544
    • 6-(difluoromethylsulfanyl)-1,3-benzothiazol-2-amine
    • 6-((difluoromethyl)thio)benzo[d]thiazol-2-amine
    • 6-(Difluoromethyl)sulfanyl-1,3-benzothiazol-2-amine
    • Inchi: 1S/C8H6F2N2S2/c9-7(10)13-4-1-2-5-6(3-4)14-8(11)12-5/h1-3,7H,(H2,11,12)
    • InChI Key: ISUPFQHWEVPYBU-UHFFFAOYSA-N
    • SMILES: S1C(N)=NC2C=CC(=CC1=2)SC(F)F

Computed Properties

  • Exact Mass: 231.99404687Da
  • Monoisotopic Mass: 231.99404687Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 206
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 3.5
  • Topological Polar Surface Area: 92.5?2

Experimental Properties

  • Density: 1.5±0.1 g/cm3
  • Melting Point: NA
  • Boiling Point: 341.5±52.0 °C at 760 mmHg
  • Vapor Pressure: 0.0±0.7 mmHg at 25°C

6-(Difluoromethyl)sulfanyl-1,3-benzothiazol-2-amine Security Information

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Additional information on 6-(Difluoromethyl)sulfanyl-1,3-benzothiazol-2-amine

Professional Introduction to Compound with CAS No 325731-49-5 and Product Name: 6-(Difluoromethyl)sulfanyl-1,3-benzothiazol-2-amine

The compound with the CAS number 325731-49-5 and the product name 6-(Difluoromethyl)sulfanyl-1,3-benzothiazol-2-amine represents a significant advancement in the field of pharmaceutical chemistry. This heterocyclic compound, featuring a benzothiazole core structure modified with a difluoromethylsulfanyl group, has garnered considerable attention due to its unique chemical properties and promising biological activities. The benzothiazole moiety is well-documented for its role in medicinal chemistry, particularly in the development of antimicrobial, anti-inflammatory, and anticancer agents. The introduction of the difluoromethylsulfanyl substituent further enhances its pharmacological potential by influencing both metabolic stability and binding affinity to biological targets.

Recent research has highlighted the importance of fluorinated aromatic compounds in drug design. The presence of fluorine atoms, especially in the difluoromethyl configuration, can modulate the electronic properties of molecules, leading to improved bioavailability and reduced susceptibility to enzymatic degradation. In the case of 6-(Difluoromethyl)sulfanyl-1,3-benzothiazol-2-amine, the dual fluorine atoms at the methyl group contribute to enhanced lipophilicity and metabolic resistance, making it an attractive candidate for further pharmacokinetic optimization. This compound has been extensively studied for its potential applications in treating various diseases, including those associated with inflammation and infection.

The structural framework of 6-(Difluoromethyl)sulfanyl-1,3-benzothiazol-2-amine also lends itself to diverse chemical modifications. Researchers have explored its reactivity in synthesizing novel derivatives with tailored biological activities. For instance, the amine functionality at the 2-position provides a site for further derivatization, enabling the creation of prodrugs or analogs with enhanced therapeutic efficacy. The sulfanyl group introduces a polar moiety that can improve solubility while maintaining interactions with biological targets. These attributes make this compound a valuable scaffold for drug discovery programs aimed at addressing unmet medical needs.

One of the most compelling aspects of 6-(Difluoromethyl)sulfanyl-1,3-benzothiazol-2-amine is its potential in modulating immune responses. Emerging studies suggest that benzothiazole derivatives can interact with various immunoregulatory pathways, making them promising candidates for immunotherapy. The difluoromethylsulfanyl group may enhance binding affinity to receptors involved in immune signaling, thereby modulating inflammatory processes. This has implications for developing treatments for autoimmune diseases and chronic infections where immune dysregulation plays a critical role.

Moreover, the compound's mechanism of action has been investigated in vitro and in vivo models. Preliminary data indicate that it can inhibit key enzymes involved in inflammatory pathways, such as cyclooxygenase (COX) and lipoxygenase (LOX). The presence of fluorine atoms may enhance enzyme inhibition by improving binding interactions within the active site. Such inhibitory effects could translate into therapeutic benefits for conditions like rheumatoid arthritis or inflammatory bowel disease. Further preclinical studies are underway to elucidate its full pharmacological profile and potential side effects.

The synthesis of 6-(Difluoromethyl)sulfanyl-1,3-benzothiazol-2-amine involves multi-step organic reactions that highlight the ingenuity of modern synthetic chemistry. Key steps include nucleophilic substitution reactions to introduce the sulfanyl group and protection-deprotection strategies to handle sensitive functional groups like the amine. Advanced techniques such as palladium-catalyzed cross-coupling reactions have been employed to construct the benzothiazole core efficiently. These synthetic methodologies not only ensure high yields but also allow for scalability, which is crucial for industrial production.

The compound's stability under various conditions has also been thoroughly evaluated. Studies have shown that it maintains structural integrity under standard storage conditions but may degrade under extreme pH or temperature variations. Understanding these stability profiles is essential for formulating effective pharmaceutical products that ensure long shelf life and consistent bioavailability. Efforts are ongoing to optimize storage conditions and develop formulations that mitigate degradation risks.

In conclusion, 6-(Difluoromethyl)sulfanyl-1,3-benzothiazol-2-amine represents a significant advancement in medicinal chemistry with its unique structural features and promising biological activities. Its potential applications in treating inflammation-related diseases and its favorable pharmacokinetic properties make it an attractive candidate for further development. As research continues to uncover new insights into its mechanisms of action and synthetic possibilities, this compound is poised to play a vital role in addressing critical medical challenges.

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