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CS-W001157 4
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2,3,4,5-Tetrahydro-1H-3-benzazepine

  • CAS No. 4424-20-8

  • Cat. No. CS-0139564
  • Molecule weightNone
  • Purity≥95%
  • MDL No.MFCD04012620

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

2,3,4,5-Tetrahydro-1H-3-benzazepine|CS-0139564

Structure of 4424-20-8

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General Information

  • CAS No. 4424-20-8
  • Cat. No. CS-0139564
  • Purity ≥95%
  • MDL No. MFCD04012620
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₃N
  • Molecular Weight None
  • Synonym(s) 2,3,4,5-Tetrahydro-1H-benzo[d]azepine
  • SMILES C12=CC=CC=C1CCNCC2

Description

This tetrahydrobenzazepine scaffold delivers a rigid, electron-rich aromatic core ideal for medicinal chemistry applications. Featuring a fully saturated seven-membered ring fused to benzene, it provides structural stability and enhanced metabolic resistance. The planar geometry facilitates π-stacking interactions in target binding sites, enabling efficient incorporation into CNS-active compounds.

Application

2,3,4,5-Tetrahydro-1H-3-benzazepine serves as a versatile scaffold in medicinal chemistry, enabling the construction of bioactive heterocycles through standard functionalization at the nitrogen and aromatic positions. Its stable, partially saturated ring system offers favorable handling characteristics and compatibility with common coupling reactions, facilitating rapid analog generation for target-directed synthesis.

Synthesis

  • Route1

    References

    • Macdonald, Gregor J.; Branch, Clive L.; Hadley, Michael S.; Johnson, Christopher N.; Nash, David J.; Smith, Alexander B.; Stemp, Geoffrey; Thewlis, Kevin M.; Vong, Antonio K. K.; Austin, Nigel E.; Jeffrey, Phillip; Winborn, Kim Y.; Boyfield, Izzy; Hagan, Jim J.; Middlemiss, Derek N.; Reavill, Charlie; Riley, Graham J.; Watson, Jeannette M.; Wood, Martyn; Parker, Steve G.; Ashby Jr., Charles R. Journal of Medicinal Chemistry, 2003 , vol. 46, # 23 p. 4952 - 4964
  • Route2
    • null|null
      130800-04-3
    • ~78%
    • In-stock
      2,3,4,5-Tetrahydro-1H-3-benzazepine|CS-0139564
      4424-20-8

    References

    • CEPHALON, INC.; PHARMACOPEIA DRUG DISCOVERY, INC. Patent: WO2008/51547 A1, 2008 ; Location in patent: Page/Page column 259; 315 ; WO 2008/051547 A1
  • Route3
    • null|null
      215033-43-5
    • ~77%
    • In-stock
      2,3,4,5-Tetrahydro-1H-3-benzazepine|CS-0139564
      4424-20-8

    References

    • Toda, Jun; Ichikawa, Tsuyoshi; Saitoh, Toshiaki; Horiguchi, Yoshie; Sano, Takehiro Heterocycles, 2000 , vol. 53, # 9 p. 2009 - 2018

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 3259
Class : 8
Packing Group : Ⅲ
Hazard Statements : H314-H318
Precautionary Statements : P260-P264-P280-P301+P330+P331-P304+P340-P363-P405-P501

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Computational Chemistry Data

  • TPSA   12.03
  • LogP   1.3748
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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