Cas no 184637-11-4 (6-Bromo-1-(tert-butyldimethylsilyl)indole)

6-Bromo-1-(tert-butyldimethylsilyl)indole is a protected indole derivative featuring a bromine substituent at the 6-position and a tert-butyldimethylsilyl (TBS) group at the 1-position. The TBS protection enhances stability, preventing undesired reactions at the indole nitrogen during synthetic transformations. The bromine moiety serves as a versatile handle for further functionalization via cross-coupling reactions, such as Suzuki or Negishi couplings. This compound is particularly useful in medicinal chemistry and materials science, where selective modifications of the indole scaffold are required. Its high purity and well-defined reactivity make it a valuable intermediate for constructing complex heterocyclic systems.
6-Bromo-1-(tert-butyldimethylsilyl)indole structure
184637-11-4 structure
Product Name:6-Bromo-1-(tert-butyldimethylsilyl)indole
CAS No:184637-11-4
MF:C14H20BrNSi
MW:310.304803848267
MDL:MFCD17926506
CID:850637
PubChem ID:10518990
Update Time:2025-05-28

6-Bromo-1-(tert-butyldimethylsilyl)indole Chemical and Physical Properties

Names and Identifiers

    • 1H-Indole, 6-bromo-1-[(1,1-dimethylethyl)dimethylsilyl]-
    • 6-BROMO-1-(TERT-BUTYLDIMETHYLSILYL)INDOLE
    • 1-(TERT-BUTYLDIMETHYLSILYL)-6-BROMO-1H-INDOLE
    • 184637-11-4
    • EN300-178026
    • DTXSID80441210
    • 6-Bromo-1-(tert-Butyl dimethylsilyl)indole
    • MFCD17926506
    • 6-Bromo-1-(tert-butyldimethylsilyl)-1H-indole
    • BS-25461
    • DB-369015
    • AKOS015835899
    • (6-bromoindol-1-yl)-tert-butyl-dimethylsilane
    • 6-Bromo-1-(tert-butyldimethylsilyl)indole
    • MDL: MFCD17926506
    • Inchi: 1S/C14H20BrNSi/c1-14(2,3)17(4,5)16-9-8-11-6-7-12(15)10-13(11)16/h6-10H,1-5H3
    • InChI Key: YNLGCNHZTPJVQK-UHFFFAOYSA-N
    • SMILES: BrC1C=CC2C=CN(C=2C=1)[Si](C)(C)C(C)(C)C

Computed Properties

  • Exact Mass: 309.05500
  • Monoisotopic Mass: 309.05484g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 2
  • Complexity: 284
  • 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
  • Topological Polar Surface Area: 4.9?2

Experimental Properties

  • PSA: 4.93000
  • LogP: 5.25710

6-Bromo-1-(tert-butyldimethylsilyl)indole 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-Bromo-1-(tert-butyldimethylsilyl)indole Production Method

Additional information on 6-Bromo-1-(tert-butyldimethylsilyl)indole

Comprehensive Overview of 6-Bromo-1-(tert-butyldimethylsilyl)indole (CAS No. 184637-11-4)

6-Bromo-1-(tert-butyldimethylsilyl)indole (CAS No. 184637-11-4) is a highly versatile heterocyclic compound widely utilized in pharmaceutical research, organic synthesis, and material science. This silyl-protected indole derivative has garnered significant attention due to its unique chemical properties, making it a valuable intermediate in the development of bioactive molecules and advanced materials. Researchers and industry professionals frequently search for terms like "6-Bromo-1-TBS indole synthesis," "CAS 184637-11-4 applications," and "TBS-protected indole derivatives," reflecting its growing relevance in modern chemistry.

The compound's structure features a bromine substituent at the 6-position of the indole ring, coupled with a tert-butyldimethylsilyl (TBS) protecting group at the 1-position. This combination enhances its stability and reactivity, enabling precise functionalization in multi-step synthetic routes. Recent trends in green chemistry and sustainable synthesis have spurred interest in optimizing its preparation methods, with queries such as "eco-friendly synthesis of 6-Bromo-1-TBS indole" gaining traction. Its role in cross-coupling reactions, particularly in palladium-catalyzed transformations, further underscores its importance in constructing complex molecular architectures.

In pharmaceutical applications, 6-Bromo-1-(tert-butyldimethylsilyl)indole serves as a key precursor for drug discovery projects targeting central nervous system (CNS) disorders and anticancer agents. The bromoindole scaffold is a privileged structure in medicinal chemistry, often explored for its kinase inhibition and receptor modulation potential. Online searches frequently include phrases like "6-Bromo-1-TBS indole in drug development" and "CAS 184637-11-4 biological activity," highlighting its interdisciplinary appeal. Additionally, its compatibility with high-throughput screening platforms aligns with the demand for fragment-based drug design strategies.

From a commercial perspective, the compound's availability and purity are critical for reproducibility in research. Suppliers often emphasize HPLC-grade 6-Bromo-1-(tert-butyldimethylsilyl)indole to meet stringent quality standards, addressing common search queries like "buy 6-Bromo-1-TBS indole high purity." Analytical techniques such as NMR spectroscopy and mass spectrometry are routinely employed to verify its structural integrity, ensuring reliable performance in sensitive applications. The compound's storage conditions (e.g., inert atmosphere, low temperature) are also frequently discussed topics among end-users.

Emerging applications in material science further expand the utility of CAS No. 184637-11-4. Its incorporation into organic semiconductors and luminescent materials has been explored, driven by the indole core's electron-rich nature. Searches related to "6-Bromo-1-TBS indole in OLEDs" or "conductive polymers from bromoindoles" reflect this niche yet growing interest. The compound's adaptability to click chemistry protocols also positions it as a building block for functionalized surfaces and nanostructured materials.

In summary, 6-Bromo-1-(tert-butyldimethylsilyl)indole (CAS No. 184637-11-4) represents a cornerstone in contemporary chemical research. Its multifaceted roles—from enabling precision synthesis to advancing therapeutic innovation—resonate with diverse scientific communities. By addressing trending search terms like "6-Bromo-1-TBS indole safety data" and "scalable production methods," this overview bridges technical depth with practical insights, catering to both novice and expert audiences in the field.

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