Date published: 2025-10-13

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4-Azaindole (CAS 272-49-1)

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Alternate Names:
1H-Pyrrolo[3,2-b]pyridine
CAS Number:
272-49-1
Purity:
≥98%
Molecular Weight:
118.14
Molecular Formula:
C7H6N2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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4-Azaindole is a heterocyclic compound that functions as a building block in organic synthesis. It is used as a precursor in the preparation of various agrochemicals and materials. Its mechanism of action involves participating in a range of chemical reactions, including nucleophilic substitution, electrophilic aromatic substitution, and metal-catalyzed cross-coupling reactions. In these processes, 4-Azaindole can act as a nucleophile, electrophile, or ligand, facilitating the formation of new carbon-carbon and carbon-heteroatom bonds. 4-Azaindole′s unique structure and reactivity make it versatile for the construction of complex molecular architectures, enabling the synthesis of diverse chemical entities with potential applications in various research and development fields.


4-Azaindole (CAS 272-49-1) References

  1. Azaindoles: moderately basic P1 groups for enhancing the selectivity of thrombin inhibitors.  |  Sanderson, PE., et al. 2003. Bioorg Med Chem Lett. 13: 795-8. PMID: 12617893
  2. Preparation of 4-azaindole and 7-azaindole dimers with a bisalkoxyalkyl spacer in order to preferentially target melatonin MT1 receptors over melatonin MT2 receptors.  |  Larraya, C., et al. 2004. Eur J Med Chem. 39: 515-26. PMID: 15183910
  3. Excited state tautomerization of azaindole.  |  Cash, MT., et al. 2005. Org Biomol Chem. 3: 3701-6. PMID: 16211105
  4. Discovery of 4-azaindoles as novel inhibitors of c-Met kinase.  |  Porter, J., et al. 2009. Bioorg Med Chem Lett. 19: 2780-4. PMID: 19369077
  5. Blue fluorescent amino acids as in vivo building blocks for proteins.  |  Merkel, L., et al. 2010. Chembiochem. 11: 305-14. PMID: 20058252
  6. Structure-based optimization of potent 4- and 6-azaindole-3-carboxamides as renin inhibitors.  |  Scheiper, B., et al. 2011. Bioorg Med Chem Lett. 21: 5480-6. PMID: 21840218
  7. Spectroscopic study of the ground and excited state prototropic equilibria of 4-azaindole.  |  Carnerero, JM., et al. 2012. Spectrochim Acta A Mol Biomol Spectrosc. 97: 1072-8. PMID: 22925984
  8. Efficient asymmetric synthesis of tryptophan analogues having useful photophysical properties.  |  Talukder, P., et al. 2014. Org Lett. 16: 556-9. PMID: 24392870
  9. Discovery of 4-Azaindole Inhibitors of TGFβRI as Immuno-oncology Agents.  |  Zhang, Y., et al. 2018. ACS Med Chem Lett. 9: 1117-1122. PMID: 30429955
  10. 1 H-15 N HMBC NMR as a tool for rapid identification of isomeric azaindoles: The case of 5F-MDMB-P7AICA.  |  Martek, BA., et al. 2019. Drug Test Anal. 11: 617-625. PMID: 30730110
  11. In vitro anticancer active cis-Pt(II)-diiodido complexes containing 4-azaindoles.  |  Štarha, P., et al. 2019. J Biol Inorg Chem. 24: 257-269. PMID: 30767079
  12. A novel combination regimen of BET and FLT3 inhibition for FLT3-ITD acute myeloid leukemia.  |  Lee, L., et al. 2021. Haematologica. 106: 1022-1033. PMID: 33504139
  13. Identification of novel indole derivatives as highly potent AMPK activators with anti-diabetic profiles.  |  Tamura, Y., et al. 2022. Bioorg Med Chem Lett. 68: 128769. PMID: 35513222

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

4-Azaindole, 500 mg

sc-280412A
500 mg
$54.00

4-Azaindole, 1 g

sc-280412
1 g
$95.00