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CS-W001157 4
Total: USD 88.00

6-Nitro-1,2,3,4-tetrahydroisoquinoline

  • CAS No. 186390-77-2

  • Cat. No. CS-D1801
  • Molecule weight178.19
  • Purity≥95%
  • MDL No.MFCD02684189

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

6-Nitro-1,2,3,4-tetrahydroisoquinoline|CS-D1801

Structure of 186390-77-2

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General Information

  • CAS No. 186390-77-2
  • Cat. No. CS-D1801
  • Purity ≥95%
  • MDL No. MFCD02684189
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₀N₂O₂
  • Molecular Weight 178.19
  • Synonym(s) 6-nitro-3,4-dihydro-1H-2l2-isoquinoline
  • SMILES O=[N+](C1=CC2=C(CNCC2)C=C1)[O-]

Description

6-Nitro-1,2,3,4-tetrahydroisoquinoline features a fused bicyclic scaffold with a nitro group at the C6 position, imparting strong electron-withdrawing character. This structural motif enables direct incorporation into bioactive molecule design, particularly in medicinal chemistry scaffolds requiring modulated electronic properties and enhanced metabolic stability.

Application

6-Nitro-1,2,3,4-tetrahydroisoquinoline serves as a versatile building block in medicinal chemistry, enabling the synthesis of bioactive heterocycles through standard reduction and functionalization protocols. Its nitro group facilitates selective transformations such as reductive amination, coupling reactions, and cyclization cascades. The scaffold exhibits good bench stability and compatibility with common protecting groups, making it well-suited for iterative synthetic strategies in API development.

Synthesis

  • Route1

    References

    • CELLZOME AG Patent: WO2009/62658 A1, 2009 ; Location in patent: Page/Page column 36 ; WO 2009/062658 A1
  • Route2
    • null|null
      124-63-0
    • 2-(2-(Hydroxymethyl)-5-nitrophenyl)ethanol|CS-M0237
      186390-74-9
    • ~%
    • In-stock
      6-Nitro-1,2,3,4-tetrahydroisoquinoline|CS-D1801
      186390-77-2

    References

    • PFIZER INC. Patent: EP1181954 A2, 2002 ;
  • Route3
    • 2-(2-(Methylsulfonyloxy)ethyl)-4-nitrobenzyl methanesulfonate|CS-M0238
      199014-22-7
    • ~%
    • In-stock
      6-Nitro-1,2,3,4-tetrahydroisoquinoline|CS-D1801
      186390-77-2

    References

    • Quallich, George J.; Makowski, Teresa W.; Sanders, Andrew F.; Urban, Frank J.; Vazquez, Enrique Journal of Organic Chemistry, 1998 , vol. 63, # 12 p. 4116 - 4119

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-H320-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   55.17
  • LogP   1.2405
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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