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CS-W001157 4
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4-Bromophthalazin-1(2H)-one

  • CAS No. 19064-73-4

  • Cat. No. CS-0041952
  • Purity≥95%
  • MDL No.None

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

4-Bromophthalazin-1(2H)-one|CS-0041952

Structure of 19064-73-4

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General Information

  • CAS No. 19064-73-4
  • Cat. No. CS-0041952
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅BrN₂O
  • Molecular Weight 225.04
  • Synonym(s) 4-bromo-2H-phthalazin-1-one
  • SMILES O=C1NN=C(Br)C2=C1C=CC=C2

Description

4-Bromophthalazin-1(2H)-one features a brominated phthalazine core with a lactam functionality, offering a versatile scaffold for medicinal chemistry. The electron-deficient ring system enables efficient coupling reactions, while the bench-stable nature facilitates handling under standard conditions. This compound serves as a key intermediate in synthesizing bioactive heterocycles and pharmaceutical candidates.

Application

4-Bromophthalazin-1(2H)-one serves as a versatile building block for heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its stable bromo substituent. The phthalazinone core provides inherent rigidity and hydrogen-bonding capacity, enhancing solubility and crystallinity during purification. This compound exhibits excellent bench stability and functional group tolerance, facilitating downstream modifications in medicinal chemistry campaigns targeting kinase inhibitors and other bioactive scaffolds.

Synthesis

  • Route1

    References

    • F. HOFFMANN-LA ROCHE AG Patent: WO2006/32518 A1, 2006 ; Location in patent: Page/Page column 154; 155 ; WO 2006/032518 A1
  • Route2

    References

    • F. HOFFMANN-LA ROCHE AG Patent: WO2006/32518 A1, 2006 ; Location in patent: Page/Page column 154 ; WO 2006/032518 A1
  • Route3

    References

    • Prime, Michael E.; Courtney, Stephen M.; Brookfield, Frederick A.; Marston, Richard W.; Walker, Victoria; Warne, Justin; Boyd, Andrew E.; Kairies, Norman A.; Von Der Saal, Wolfgang; Limberg, Anja; Georges, Guy; Engh, Richard A.; Goller, Bernhard; Rueger, Petra; Rueth, Matthias Journal of Medicinal Chemistry, 2011 , vol. 54, # 1 p. 312 - 319

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-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   45.75
  • LogP   1.6856
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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