Cas no 6278-86-0 (N-(4-Bromophenyl)benzodthiazol-2-amine)

N-(4-Bromophenyl)benzothiazol-2-amine is a brominated benzothiazole derivative with applications in organic synthesis and pharmaceutical research. Its structure features a benzothiazole core linked to a 4-bromophenyl group via an amine bridge, offering versatility as a building block for heterocyclic compounds. The bromine substituent enhances reactivity in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, facilitating further functionalization. This compound is valued for its stability and potential as an intermediate in the development of bioactive molecules, including antimicrobial or antitumor agents. Its well-defined molecular architecture makes it suitable for mechanistic studies and material science applications.
N-(4-Bromophenyl)benzodthiazol-2-amine structure
6278-86-0 structure
Product Name:N-(4-Bromophenyl)benzodthiazol-2-amine
CAS No:6278-86-0
MF:C13H9BrN2S
MW:305.192960500717
MDL:MFCD03460423
CID:957890
PubChem ID:234496
Update Time:2025-05-26

N-(4-Bromophenyl)benzodthiazol-2-amine Chemical and Physical Properties

Names and Identifiers

    • N-(4-Bromophenyl)benzo[d]thiazol-2-amine
    • N-(4-bromophenyl)-1,3-benzothiazol-2-amine
    • 2-(4-Brom-anilino)-benzthiazol
    • 2-benzothiazolamine, n-(4-bromophenyl)-
    • AC1L5SCJ
    • AC1Q266S
    • benzothiazol-2-yl-(4-bromo-phenyl)-amine
    • Benzothiazol-2-yl-(4-brom-phenyl)-amin
    • CTK2F4230
    • N-(4-bromophenyl)-2-benzothiazolamine
    • N-(4-bromophenyl)benzothiazol-2-amine
    • N-(4-bromophenyl)benzothiazol-2-ylamine
    • N2-(4-bromophenyl)-1,3-benzothiazol-2-amine
    • NSC34473
    • IFLAB-BB F1285-0798
    • SCHEMBL1752748
    • VNHLHHAXIJZPQO-UHFFFAOYSA-N
    • NSC-34473
    • D82546
    • AKOS005067287
    • CS-0155907
    • DTXSID80283955
    • MFCD03460423
    • STK680390
    • BS-17311
    • N-(1,3-BENZOTHIAZOL-2-YL)-N-(4-BROMOPHENYL)AMINE
    • 6278-86-0
    • N-(4-Bromophenyl)benzodthiazol-2-amine
    • MDL: MFCD03460423
    • Inchi: 1S/C13H9BrN2S/c14-9-5-7-10(8-6-9)15-13-16-11-3-1-2-4-12(11)17-13/h1-8H,(H,15,16)
    • InChI Key: VNHLHHAXIJZPQO-UHFFFAOYSA-N
    • SMILES: BrC1C=CC(=CC=1)NC1=NC2C=CC=CC=2S1

Computed Properties

  • Exact Mass: 303.96707
  • Monoisotopic Mass: 303.967
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 2
  • Complexity: 256
  • 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: 4.8
  • Topological Polar Surface Area: 53.2A^2

Experimental Properties

  • Density: 1.619
  • Boiling Point: 416.6°C at 760 mmHg
  • Flash Point: 205.8°C
  • Refractive Index: 1.761
  • PSA: 24.92
  • LogP: 4.87540

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Additional information on N-(4-Bromophenyl)benzodthiazol-2-amine

Introduction to N-(4-Bromophenyl)benzodithiazol-2-amine and Its Significance in Modern Chemical Research

N-(4-Bromophenyl)benzodithiazol-2-amine, a compound with the CAS number 6278-86-0, represents a fascinating molecule in the realm of chemical biology and pharmaceutical development. This heterocyclic amine, characterized by its brominated phenyl ring and dithiazole core, has garnered significant attention due to its versatile structural features and potential applications in medicinal chemistry.

The structural motif of N-(4-bromophenyl)benzodithiazol-2-amine consists of a benzodithiazole scaffold, which is a well-known pharmacophore in the design of bioactive molecules. The presence of two sulfur atoms in the dithiazole ring enhances its reactivity and binding affinity to biological targets. Furthermore, the 4-bromophenyl group introduces a hydrophobic pocket that can be exploited for interactions with specific amino acid residues in proteins.

In recent years, there has been a surge in research focused on developing novel heterocyclic compounds for therapeutic purposes. N-(4-Bromophenyl)benzodithiazol-2-amine has emerged as a promising candidate due to its ability to modulate various biological pathways. Its unique structural features make it an attractive scaffold for drug discovery, particularly in the quest for new treatments against neurological disorders, cancer, and infectious diseases.

One of the most compelling aspects of N-(4-Bromophenyl)benzodithiazol-2-amine is its potential as an intermediate in the synthesis of more complex pharmacological agents. The bromine atom on the phenyl ring provides a handle for further functionalization via cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings. These reactions allow chemists to attach diverse substituents, thereby tailoring the compound's properties to achieve desired biological effects.

Recent studies have highlighted the role of benzodithiazole derivatives in inhibiting enzymes and receptors involved in disease pathogenesis. For instance, N-(4-bromophenyl)benzodithiazol-2-amine has been investigated for its potential to interact with kinases and transcription factors. Its ability to disrupt aberrant signaling pathways makes it a valuable tool in preclinical research aimed at understanding disease mechanisms and identifying new therapeutic targets.

The pharmaceutical industry has shown particular interest in developing small-molecule inhibitors based on heterocyclic scaffolds like benzodithiazole. N-(4-Bromophenyl)benzodithiazol-2-amine exemplifies how structural modifications can enhance drug-like properties such as solubility, bioavailability, and metabolic stability. By optimizing these parameters, researchers aim to develop lead compounds that can progress through clinical trials and ultimately reach patients in need.

In addition to its pharmacological potential, N-(4-Bromophenyl)benzodithiazol-2-amine has found applications in materials science. Its electronic properties make it suitable for use in organic semiconductors and optoelectronic devices. The bromine substituent also facilitates further chemical modifications, enabling the creation of novel materials with tailored functionalities.

The synthesis of N-(4-Bromophenyl)benzodithiazol-2-amine involves multi-step organic transformations that showcase the ingenuity of synthetic chemists. Key steps include the formation of the dithiazole ring through cyclization reactions and subsequent introduction of the 4-bromophenyl group via halogenation or cross-coupling techniques. These synthetic strategies highlight the importance of understanding reaction mechanisms and developing efficient synthetic routes for complex molecules.

As research continues to uncover new applications for N-(4-Bromophenyl)benzodithiazol-2-amine, its significance in chemical biology and pharmaceutical development is likely to grow. The compound's unique structural features and versatile reactivity make it a cornerstone of modern drug discovery efforts. By leveraging its potential, scientists aim to develop innovative therapies that address unmet medical needs and improve patient outcomes.

The future of N-(4-Bromophenyl)benzodithiazol-2-amine looks promising as researchers explore new synthetic methodologies and expand its applications across multiple disciplines. Whether used as a building block for drug development or a component in advanced materials, this compound exemplifies the power of heterocyclic chemistry to drive innovation and progress.

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