Cas no 145901-11-7 (1H-Pyrrolo[2,3-b]pyridin-6-amine)

1H-Pyrrolo[2,3-b]pyridin-6-amine is a heterocyclic amine compound featuring a fused pyrrolopyridine core structure. This scaffold is of significant interest in medicinal chemistry due to its versatility as a building block for biologically active molecules, particularly in kinase inhibitor design and other therapeutic applications. The presence of the amine group at the 6-position allows for further functionalization, enabling the synthesis of diverse derivatives. Its rigid aromatic structure contributes to favorable binding interactions in target proteins. The compound is typically handled under inert conditions due to potential sensitivity to oxidation. High-purity grades are available for research applications, ensuring reproducibility in synthetic and pharmacological studies.
1H-Pyrrolo[2,3-b]pyridin-6-amine structure
145901-11-7 structure
Product Name:1H-Pyrrolo[2,3-b]pyridin-6-amine
CAS No:145901-11-7
MF:C7H7N3
MW:133.150580644608
MDL:MFCD08272224
CID:137115
PubChem ID:10419227
Update Time:2025-08-02

1H-Pyrrolo[2,3-b]pyridin-6-amine Chemical and Physical Properties

Names and Identifiers

    • 1H-Pyrrolo[2,3-b]pyridin-6-amine
    • 6-Amino-7-azaindole
    • 6-NITRO-1H-PYRROLO[2,3-B]PYRIDINE
    • 1H-Pyrrolo[2,3-b]pyridin-6-ylaMine
    • 1H-Pyrrolo[2,3-b]pyridin-6-amine(9CI)
    • OHPOAAFCWFZVPF-UHFFFAOYSA-N
    • SCHEMBL1334813
    • BCP21953
    • AMY9104
    • 1H-Pyrrolo[2,3-b]pyridin-6-amine, AldrichCPR
    • EN300-121849
    • FT-0645480
    • DS-11305
    • DTXSID00439513
    • AKOS006286249
    • CS-W019627
    • AC-7358
    • A808424
    • 145901-11-7
    • AB44400
    • Z1198176781
    • A808423
    • SY005904
    • MFCD08272224
    • MDL: MFCD08272224
    • Inchi: 1S/C7H7N3/c8-6-2-1-5-3-4-9-7(5)10-6/h1-4H,(H3,8,9,10)
    • InChI Key: OHPOAAFCWFZVPF-UHFFFAOYSA-N
    • SMILES: N1C=CC2=CC=C(N)N=C12

Computed Properties

  • Exact Mass: 133.06400
  • Monoisotopic Mass: 133.063997236g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 0
  • Complexity: 126
  • 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: 1
  • Topological Polar Surface Area: 54.7?2

Experimental Properties

  • Color/Form: No data avaiable
  • Density: 1.41±0.1 g/cm3 (20 oC 760 Torr),
  • Melting Point: 126.7 oC
  • Boiling Point: 318.4±11.0 °C at 760 mmHg
  • Flash Point: 195.469℃
  • Refractive Index: 1.78
  • Solubility: Slightly soluble (2.9 g/l) (25 o C),
  • PSA: 54.70000
  • LogP: 1.72630
  • Vapor Pressure: 0.0±0.7 mmHg at 25°C

1H-Pyrrolo[2,3-b]pyridin-6-amine 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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1H-Pyrrolo[2,3-b]pyridin-6-amine Production Method

Additional information on 1H-Pyrrolo[2,3-b]pyridin-6-amine

1H-Pyrrolo[2,3-b]pyridin-6-amine: A Comprehensive Overview

1H-Pyrrolo[2,3-b]pyridin-6-amine, identified by the CAS registry number 145901-11-7, is a heterocyclic aromatic amine compound with significant potential in various fields of organic chemistry and materials science. This compound has garnered attention due to its unique structural properties and promising applications in drug discovery, optoelectronics, and advanced materials. The molecule consists of a pyrrolopyridine core with an amino group at the 6-position, which imparts distinctive electronic and steric characteristics.

The synthesis of 1H-Pyrrolo[2,3-b]pyridin-6-amine involves a series of well-established organic reactions, including cyclization and amination processes. Recent advancements in catalytic methods have enabled more efficient and selective syntheses, reducing production costs and enhancing the overall yield. Researchers have explored various precursors, such as indole derivatives and pyridine analogs, to optimize the synthesis pathway. These developments underscore the compound's versatility as a building block in medicinal chemistry.

One of the most notable applications of 1H-Pyrrolo[2,3-b]pyridin-6-amine lies in its use as a ligand in transition metal-catalyzed reactions. Its ability to coordinate with metals such as palladium and platinum has made it valuable in cross-coupling reactions, which are pivotal in synthesizing complex organic molecules. Recent studies have demonstrated its effectiveness in Suzuki-Miyaura couplings under mild conditions, highlighting its role in sustainable chemical synthesis.

In the realm of materials science, 1H-Pyrrolo[2,3-b]pyridin-6-amine has been investigated for its potential in organic electronics. The compound's conjugated π-system allows for efficient charge transport properties, making it a candidate for applications in organic light-emitting diodes (OLEDs) and field-effect transistors (FETs). Collaborative efforts between chemists and engineers have led to the development of novel materials incorporating this compound, showcasing its adaptability across disciplines.

The biological activity of 1H-Pyrrolo[2,3-b]pyridin-6-amine has also been a focal point of recent research. Preclinical studies indicate that it exhibits moderate inhibitory effects on certain kinase enzymes, suggesting its potential as a lead compound in anticancer drug development. Additionally, its ability to modulate ion channels has opened avenues for exploring its role in treating neurological disorders. These findings emphasize the compound's dual significance in both therapeutic and non-therapeutic applications.

In terms of physical properties, 1H-Pyrrolo[2,3-b]pyridin-6-amine demonstrates a high melting point (~280°C) and good solubility in polar solvents such as dimethylformamide (DMF) and dichloromethane (DCM). Its UV-vis spectrum reveals strong absorption bands in the visible region, indicative of its electronic transitions within the conjugated system. These properties make it suitable for use in sensors and optoelectronic devices where precise control over optical characteristics is essential.

The environmental impact of CAS No. 145901-11-7 has also been evaluated to ensure sustainable practices during its production and application. Studies suggest that the compound degrades under specific environmental conditions without posing significant risks to aquatic life or soil ecosystems. This aligns with global efforts to promote green chemistry principles across industries.

In conclusion, 1H-Pyrrolo[2,3-b]pyridin-6-amine, with its unique chemical structure and diverse functional groups, continues to be a subject of intense research interest. Its applications span multiple domains, from drug discovery to advanced materials development. As scientific understanding deepens through ongoing studies and technological innovations, this compound is poised to play an increasingly important role in shaping future advancements across various sectors.

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