Cas no 928653-76-3 (5-fluoro-3-iodo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine)

5-Fluoro-3-iodo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine is a fluorinated and iodinated pyrrolopyridine derivative featuring a tris(isopropyl)silyl (TIPS) protecting group. The fluorine and iodine substituents enhance its reactivity, making it a versatile intermediate in cross-coupling reactions, such as Suzuki or Sonogashira couplings, for pharmaceutical and agrochemical applications. The TIPS group provides steric protection, improving stability during synthetic transformations. This compound is particularly valuable in medicinal chemistry for constructing complex heterocyclic scaffolds. Its high purity and well-defined structure ensure reproducibility in research and industrial processes. Suitable for controlled functionalization, it serves as a key building block in the synthesis of bioactive molecules.
5-fluoro-3-iodo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine structure
928653-76-3 structure
Product Name:5-fluoro-3-iodo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine
CAS No:928653-76-3
MF:C16H24FIN2Si
MW:418.363540649414
MDL:MFCD08741529
CID:999034
PubChem ID:329771965
Update Time:2025-05-19

5-fluoro-3-iodo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine Chemical and Physical Properties

Names and Identifiers

    • 5-FLUORO-3-IODO-1-TRIISOPROPYLSILANYL-1H-PYRROLO[2,3-B]PYRIDINE
    • 5-fluoro-3-iodo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine
    • DTXSID70640119
    • AKOS015853244
    • (5-fluoro-3-iodopyrrolo[2,3-b]pyridin-1-yl)-tri(propan-2-yl)silane
    • 5-Fluoro-3-iodo-1-[tri(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine
    • MFCD08741529
    • PB29566
    • FT-0678326
    • 5-Fluoro-3-iodo-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine
    • 5-Fluoro-3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine, AldrichCPR
    • CS-0005229
    • 928653-76-3
    • P10647
    • 5-fluoro-3-iodo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine
    • TUPFUIVWIXAUFW-UHFFFAOYSA-N
    • SCHEMBL1880673
    • DB-029540
    • HS-6918
    • 5-fluoro-3-iodo-1-(triisopropylsilyl)pyrrolo[2,3-b]pyridine
    • MDL: MFCD08741529
    • Inchi: 1S/C16H24FIN2Si/c1-10(2)21(11(3)4,12(5)6)20-9-15(18)14-7-13(17)8-19-16(14)20/h7-12H,1-6H3
    • InChI Key: TUPFUIVWIXAUFW-UHFFFAOYSA-N
    • SMILES: IC1C2=CC(=CN=C2N(C=1)[Si](C(C)C)(C(C)C)C(C)C)F

Computed Properties

  • Exact Mass: 418.07400
  • Monoisotopic Mass: 418.07375g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 21
  • Rotatable Bond Count: 4
  • Complexity: 342
  • 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: 17.8?2

Experimental Properties

  • Density: 1.37
  • Boiling Point: 356.1°C at 760 mmHg
  • Flash Point: 169.2°C
  • Refractive Index: 1.564
  • PSA: 17.82000
  • LogP: 5.80360

5-fluoro-3-iodo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine Security Information

  • Symbol: GHS07
  • Signal Word:Warning
  • Hazard Statement: H302
  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • Hazard Category Code: 22
  • Hazardous Material Identification: Xi
  • HazardClass:IRRITANT

5-fluoro-3-iodo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine Pricemore >>

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Additional information on 5-fluoro-3-iodo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine

Introduction to 5-fluoro-3-iodo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine (CAS No. 928653-76-3)

5-fluoro-3-iodo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine is a highly specialized organic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound, identified by its CAS number 928653-76-3, belongs to the class of heterocyclic compounds, which are widely recognized for their diverse biological activities and potential therapeutic applications. The unique structural features of this molecule, particularly its fluorine and iodine substituents, as well as the tris(propan-2-yl)silyl group, make it a valuable scaffold for the development of novel pharmacological agents.

The significance of 5-fluoro-3-iodo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine lies in its potential to serve as a key intermediate in the synthesis of more complex drug molecules. The presence of both fluorine and iodine atoms provides opportunities for further functionalization through cross-coupling reactions, which are fundamental in modern drug discovery. These reactions allow for the introduction of additional functional groups, enabling the creation of molecules with tailored biological properties.

In recent years, there has been a growing interest in pyrrolopyridine derivatives due to their demonstrated efficacy in various therapeutic areas. The pyrrolo[2,3-b]pyridine core is a privileged scaffold that has been extensively explored for its role in developing drugs targeting central nervous system disorders, cancer, and infectious diseases. The introduction of fluorine and iodine substituents enhances the metabolic stability and binding affinity of these compounds, making them more suitable for clinical applications.

The tris(propan-2-yl)silyl group in 5-fluoro-3-iodo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine serves multiple purposes. It acts as a protecting group during synthetic transformations, preventing unwanted side reactions while allowing for selective functionalization at other sites. Additionally, the bulky nature of this group can influence the conformation and binding properties of the molecule, which is crucial for optimizing its pharmacological activity.

Recent advancements in synthetic methodologies have enabled more efficient and scalable production of 5-fluoro-3-iodo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine. These improvements have not only reduced costs but also enhanced the quality of the final product, making it more accessible for research and development purposes. The compound is now being widely used in academic and industrial laboratories as a building block for novel drug candidates.

The biological activity of 5-fluoro-3-iodo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine has been extensively studied in various preclinical models. Initial research suggests that this compound exhibits promising properties as an inhibitor of certain enzymes and receptors involved in disease pathways. For instance, studies have shown that derivatives of this scaffold may have potential applications in treating neurological disorders by modulating neurotransmitter receptors. Furthermore, its ability to interact with specific protein targets makes it a candidate for developing anticancer agents.

The synthesis of 5-fluoro-3-iodo-1-[tris(propan-2-ylsilyl)] -1H-pyrrolo[2,3-b]pyridine involves multiple steps that require precise control over reaction conditions to ensure high yield and purity. The use of advanced catalytic systems has streamlined these processes, making it possible to produce large quantities of the compound efficiently. This has been particularly beneficial for researchers who need substantial amounts of material for their studies.

One of the most exciting aspects of working with 5-fluoro - 3 - iodo - 1 - [tris (propan - 2 - ylsilyl)] - 1H - pyrrolo [ 2 , 3 - b ] pyridine is its versatility in medicinal chemistry applications. Researchers can easily modify its structure by introducing different substituents at strategic positions, allowing for the exploration of a wide range of biological activities. This flexibility has led to numerous innovative drug candidates being developed based on this scaffold.

The future prospects for 5-fluoro - 3 - iodo - 1 - [tris (propan - 2 - ylsilyl)] - 1H - pyrrolo [ 2 , 3 - b ] pyridine are vast. As our understanding of disease mechanisms continues to evolve, so does our ability to design molecules that can effectively target them. This compound represents an excellent starting point for developing new therapies that could address unmet medical needs across multiple therapeutic areas.

In conclusion,5-fluoro - 3 - iodo - 1 - [tris (propan - 2 - ylsilyl)] - 1H-pyrrolo [ 2 , 3-b ] pyridine (CAS No .928653 .76 .3) is a remarkable compound with significant potential in pharmaceutical research . Its unique structural features , combined with its synthetic accessibility , make it an invaluable tool for drug discovery . As research progresses , we can expect to see even more innovative applications emerging from this versatile scaffold .

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