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CS-W001157 4
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3-Bromoimidazo[1,2-a]pyrazin-8-amine

  • CAS No. 117718-92-0

  • Cat. No. CS-0051439
  • Purity≥95%
  • MDL No.MFCD09265736

*For research and further manufacturing use only, not for direct human use.

3-Bromoimidazo[1,2-a]pyrazin-8-amine|CS-0051439

Structure of 117718-92-0

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General Information

  • CAS No. 117718-92-0
  • Cat. No. CS-0051439
  • Purity ≥95%
  • MDL No. MFCD09265736
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅BrN₄
  • Molecular Weight 213.04
  • Synonym(s) Bromoimidazo[1,2-a]pyrazin-8-amine
  • SMILES NC1=NC=CN2C(Br)=CN=C12

Description

3-Bromoimidazo[1,2-a]pyrazin-8-amine features a fused imidazopyrazine core with a bromine substituent at the 3-position, enabling direct functionalization in cross-coupling reactions. The electron-deficient pyrazine ring enhances reactivity in palladium-catalyzed transformations, while the amine group provides a handle for derivatization. This compound serves as a key scaffold for bioactive molecule synthesis.

Application

3-Bromoimidazo[1,2-a]pyrazin-8-amine serves as a versatile building block for heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its well-defined bromo functionality. The imidazo[1,2-a]pyrazine core offers enhanced stability and favorable electronic properties, facilitating functionalization in medicinal chemistry applications. Its compatibility with standard reaction conditions and ease of purification make it a practical choice for constructing complex scaffolds in API development.

Synthesis

  • Route1

    References

    • Schering Corporation Patent: US2007/117804 A1, 2007 ; Location in patent: Page/Page column 75 ; US 20070117804 A1
  • Route2
    • 3,8-Dibromoimidazo[1,2-a]pyrazine|CS-0085065
      936361-36-3
    • ~50%
    • In-stock
      3-Bromoimidazo[1,2-a]pyrazin-8-amine|CS-0051439
      117718-92-0

    References

    • Sugen, Inc. Patent: US2004/220189 A1, 2004 ; Location in patent: Page 22 ; US 20040220189 A1
  • Route3

    References

    • Sugen, Inc. Patent: US2005/9832 A1, 2005 ; US 20050009832 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   56.21
  • LogP   1.074
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   0

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