Cas no 640735-24-6 (4-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine)

4-Bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine is a brominated pyrrolopyridine derivative featuring a tris(isopropyl)silyl (TIPS) protecting group. The TIPS moiety enhances steric protection, improving stability during synthetic transformations, particularly in metal-catalyzed cross-coupling reactions. The bromine substituent at the 4-position serves as a versatile handle for further functionalization, enabling access to complex heterocyclic architectures. This compound is valuable in pharmaceutical and materials science research, where pyrrolopyridine scaffolds are of interest due to their bioactive and optoelectronic properties. Its robust stability and reactivity make it suitable for multistep synthetic routes, ensuring reliable performance in demanding applications.
4-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine structure
640735-24-6 structure
Product Name:4-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine
CAS No:640735-24-6
MF:C16H25BrN2Si
MW:353.372604131699
MDL:MFCD11616420
CID:832952
PubChem ID:11473655
Update Time:2025-10-28

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

Names and Identifiers

    • 1H-Pyrrolo[2,3-b]pyridine, 4-bromo-1-[tris(1-methylethyl)silyl]-
    • 4-Bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine
    • 1-triisopropyl-4-bromo-7-azaindole
    • 4-Brom-2,3,4,5-tetrahydro-5-oxo-1-p-toluolsulfonylbenz<b>azepin
    • 4-bromo-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-benzo[b]azepin-5-one
    • 4-bromo-1-[(4-methylphenyl)sulfonyl]-1,2,3
    • 4-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine
    • 4-bromo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin
    • 4-bromo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine
    • 4-BROMO-1-(TRIISOPROPYLSILYL)-7-AZAINDOLE
    • QSEMMUYKUYKNBI-UHFFFAOYSA-N
    • PB26669
    • ST1090508
    • 1-(Triisopropylsilyl)-4-bromo-7-aza-1H-indole
    • 4-bromo-1-triisopropylsilanyl-1H-pyrro
    • MFCD11616385
    • SY098775
    • SCHEMBL794853
    • DB-030862
    • MFCD11616420
    • 4-BROMO-1-(TRIISOPROPYLSILYL)PYRROLO[2,3-B]PYRIDINE
    • AKOS025289571
    • 640735-24-6
    • AS-33627
    • (4-bromopyrrolo[2,3-b]pyridin-1-yl)-tri(propan-2-yl)silane
    • CS-0004172
    • 4-Bromo-1-1-(triisopropylsilyl)-7-azaindole
    • MDL: MFCD11616420
    • Inchi: 1S/C16H25BrN2Si/c1-11(2)20(12(3)4,13(5)6)19-10-8-14-15(17)7-9-18-16(14)19/h7-13H,1-6H3
    • InChI Key: QSEMMUYKUYKNBI-UHFFFAOYSA-N
    • SMILES: BrC1C=CN=C2C=1C=CN2[Si](C(C)C)(C(C)C)C(C)C

Computed Properties

  • Exact Mass: 352.09700
  • Monoisotopic Mass: 352.09704g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 20
  • Rotatable Bond Count: 4
  • Complexity: 311
  • 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

Experimental Properties

  • PSA: 17.82000
  • LogP: 5.82240

4-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine Pricemore >>

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Additional information on 4-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine

Professional Introduction to 4-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine (CAS No. 640735-24-6)

4-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine (CAS No. 640735-24-6) is a highly specialized organic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound, characterized by its intricate molecular structure, serves as a crucial intermediate in the synthesis of various biologically active molecules. The presence of both bromine and tris(propan-2-yl)silyl functional groups makes it a versatile building block for further chemical modifications, enabling the development of novel therapeutic agents.

The bromo substituent on the pyrrolo[2,3-b]pyridine core provides a reactive site for cross-coupling reactions, such as Suzuki-Miyaura and Buchwald-Hartwig couplings, which are fundamental in constructing complex heterocyclic frameworks. These reactions are widely employed in the pharmaceutical industry to create intricate drug molecules with desired pharmacological properties. Additionally, the tris(propan-2-yl)silyl group enhances the stability of the compound during synthetic processes, preventing unwanted side reactions and ensuring high yields.

Recent advancements in synthetic methodologies have highlighted the importance of such intermediates in drug discovery. The compound's unique structure has been leveraged in the development of kinase inhibitors, which are critical in treating various cancers and inflammatory diseases. For instance, derivatives of 4-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine have shown promising activity against tyrosine kinases, a family of enzymes implicated in cell proliferation and survival.

In addition to its role in kinase inhibition, this compound has been explored in the synthesis of antiviral agents. The pyrrolo[2,3-b]pyridine scaffold is known for its ability to interact with viral proteases and polymerases, making it an attractive moiety for designing inhibitors against pathogens like HIV and hepatitis C. The bromo group facilitates further functionalization, allowing chemists to introduce additional pharmacophores that enhance binding affinity and selectivity.

The tris(propan-2-yl)silyl protective group not only stabilizes the molecule during synthetic steps but also allows for selective deprotection under mild conditions. This feature is particularly useful in multi-step syntheses where orthogonal functional groups are present. The ability to control reactivity at multiple sites enables the construction of highly complex molecules with precise structural features.

Recent studies have also demonstrated the utility of this compound in materials science. Pyrrolo[2,3-b]pyridine derivatives have been investigated for their potential applications in organic electronics due to their electron-deficient nature and ability to form stable radicals. These properties make them suitable candidates for use in organic light-emitting diodes (OLEDs) and photovoltaic cells. The bromo substituent allows for further derivatization into conjugated polymers and small-molecule emitters, expanding the range of possible applications.

The pharmaceutical industry continues to explore novel scaffolds for drug development, and 4-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine stands out as a promising candidate. Its unique structural features and reactivity make it an invaluable tool for medicinal chemists seeking to design next-generation therapeutics. As research progresses, it is expected that this compound will play an increasingly significant role in both academic and industrial settings.

The synthesis of this compound involves multi-step organic transformations that require careful optimization to achieve high yields and purity. Advanced techniques such as flow chemistry have been employed to streamline these processes, reducing reaction times and improving scalability. These advancements underscore the growing importance of specialized intermediates like 4-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine in modern drug discovery.

In conclusion, 4-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine (CAS No. 640735-24-6) is a versatile and highly valuable intermediate with broad applications in pharmaceuticals and materials science. Its unique structural features and reactivity make it an essential tool for chemists seeking to develop innovative therapeutic agents and advanced materials. As research continues to evolve, this compound is poised to remain at the forefront of scientific exploration.

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