Cas no 59609-63-1 (6-Bromogramine)

6-Bromogramine is a brominated derivative of gramine, an indole alkaloid, with the molecular formula C11H13BrN2. This compound is primarily utilized in organic synthesis and pharmaceutical research as a versatile intermediate. Its key advantages include its reactivity in cross-coupling reactions, enabling the construction of complex indole-based structures. The bromine substituent enhances its utility in nucleophilic substitution and metal-catalyzed transformations, such as Suzuki or Buchwald-Hartwig reactions. 6-Bromogramine is valued for its stability under standard conditions and its role in accessing biologically active molecules. It is commonly employed in the development of agrochemicals, pharmaceuticals, and other fine chemicals requiring indole scaffolds.
6-Bromogramine structure
6-Bromogramine structure
Product Name:6-Bromogramine
CAS No:59609-63-1
MF:C11H13BrN2
MW:253.138321638107
CID:2196714
PubChem ID:13384094
Update Time:2025-06-07

6-Bromogramine Chemical and Physical Properties

Names and Identifiers

    • 6-Bromogramine
    • Methyl 6-bromobenzo[d]thiazole-2-carboxylate;6-Bromogramine;6-BROMO-BENZOTHIAZOLE-2-CARBOXYLIC ACID METHYL ESTER;6-Bromgramin;6-bromo-3-dimethylaminomethyl-indole;
    • 6-Bromo-N,N-dimethyl-1H-indole-3-methanamine
    • 59609-63-1
    • 1-(6-Bromo-1H-indol-3-yl)-N,N-dimethylmethanamine
    • BS-29025
    • SCHEMBL6031494
    • CS-0209911
    • CKUNQRCQLWHINE-UHFFFAOYSA-N
    • [(6-BROMO-1H-INDOL-3-YL)METHYL]DIMETHYLAMINE
    • Inchi: 1S/C11H13BrN2/c1-14(2)7-8-6-13-11-5-9(12)3-4-10(8)11/h3-6,13H,7H2,1-2H3
    • InChI Key: CKUNQRCQLWHINE-UHFFFAOYSA-N
    • SMILES: BrC1C=CC2=C(C=1)NC=C2CN(C)C

Computed Properties

  • Exact Mass: 252.02600
  • Monoisotopic Mass: 252.02621g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 196
  • 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: 2.6
  • Topological Polar Surface Area: 19?2

Experimental Properties

  • PSA: 19.03000
  • LogP: 2.99200

6-Bromogramine Customs Data

  • HS CODE:2933990090
  • Customs Data:

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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6-Bromogramine Production Method

Additional information on 6-Bromogramine

Introduction to 6-Bromogramine (CAS No. 59609-63-1)

6-Bromogramine, identified by the Chemical Abstracts Service Number (CAS No.) 59609-63-1, is a significant compound in the realm of pharmaceutical and biochemical research. This compound has garnered attention due to its unique structural properties and potential applications in medicinal chemistry. The presence of a bromine substituent in its molecular framework makes it a versatile intermediate for synthesizing more complex molecules, particularly in the development of novel therapeutic agents.

The chemical structure of 6-Bromogramine features a guanidine core, which is a well-known pharmacophore in drug design. The guanidine moiety is highly relevant in medicinal chemistry due to its ability to interact with biological targets such as enzymes and receptors. The introduction of a bromine atom at the sixth position enhances its reactivity, making it an attractive building block for further functionalization. This reactivity has been exploited in various synthetic pathways to develop derivatives with enhanced pharmacological properties.

In recent years, there has been a surge in research focused on developing inhibitors targeting enzymes involved in metabolic pathways associated with diseases such as cancer, diabetes, and inflammatory disorders. 6-Bromogramine has emerged as a key intermediate in the synthesis of such inhibitors. Its brominated structure allows for easy modification through cross-coupling reactions, which are pivotal in constructing complex organic molecules. These reactions include Suzuki-Miyaura, Heck, and Buchwald-Hartwig couplings, enabling the attachment of diverse functional groups to the guanidine core.

One of the most compelling aspects of 6-Bromogramine is its role in the development of kinase inhibitors. Kinases are enzymes that play a crucial role in cell signaling pathways, and their dysregulation is often associated with various diseases, particularly cancer. Researchers have leveraged the structural flexibility of 6-Bromogramine to design molecules that selectively inhibit specific kinases without affecting others. This selectivity is critical for minimizing side effects and improving therapeutic efficacy.

Recent studies have highlighted the potential of 6-Bromogramine derivatives as antiviral agents. The guanidine moiety is known to exhibit broad-spectrum antiviral activity by interfering with viral replication mechanisms. By incorporating bromine atoms into this framework, scientists have been able to enhance the stability and bioavailability of these derivatives. This has led to the discovery of novel compounds that show promise in treating viral infections, including those caused by RNA viruses.

The synthesis of 6-Bromogramine involves multi-step organic reactions that require precise control over reaction conditions to ensure high yield and purity. The process typically begins with the bromination of a precursor molecule containing a guanidine group. Advanced synthetic techniques such as flow chemistry have been employed to optimize these reactions, improving scalability and reducing waste.

The pharmacological evaluation of 6-Bromogramine derivatives has revealed several interesting findings. In preclinical studies, certain analogs have demonstrated potent activity against target enzymes while maintaining good oral bioavailability. These findings have spurred further research into developing next-generation drugs based on this scaffold. The ability to fine-tune the chemical properties of these derivatives allows researchers to explore different therapeutic modalities, from small-molecule inhibitors to peptidomimetics.

The regulatory landscape for compounds like 6-Bromogramine is stringent but well-established, ensuring that they meet safety and efficacy standards before entering clinical trials. Manufacturers must adhere to Good Manufacturing Practices (GMP) and undergo rigorous testing to demonstrate their suitability for pharmaceutical use. This regulatory framework provides confidence to researchers and clinicians that compounds derived from intermediates like 6-Bromogramine are safe and effective for therapeutic applications.

Future directions in the research of 6-Bromogramine include exploring its potential in combination therapies and personalized medicine. By understanding how different derivatives interact with biological systems, scientists can develop treatment strategies that are tailored to individual patients' needs. Additionally, advancements in computational chemistry are enabling faster and more accurate predictions of molecular properties, accelerating the discovery process.

In conclusion,6-Bromogramine (CAS No. 59609-63-1) represents a valuable asset in pharmaceutical research due to its structural versatility and potential therapeutic applications. Its role as an intermediate in synthesizing kinase inhibitors, antiviral agents, and other bioactive molecules underscores its importance in drug discovery efforts. As research continues to uncover new applications for this compound,6-Bromogramine is poised to remain at the forefront of medicinal chemistry innovation.

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