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CS-W001157 4
Total: USD 88.00

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

  • CAS No. 226942-29-6

  • Cat. No. CS-W019599
  • Purity≥95%
  • MDL No.MFCD07374370

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

6-Bromo-1,2,3,4-tetrahydroisoquinoline|CS-W019599

Structure of 226942-29-6

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General Information

  • CAS No. 226942-29-6
  • Cat. No. CS-W019599
  • Purity ≥95%
  • MDL No. MFCD07374370
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₀BrN
  • Molecular Weight 212.09
  • Synonym(s) isoquinoline, 6-bromo-1,2,3,4-tetrahydro-
  • SMILES BrC1=CC2=C(CNCC2)C=C1

Description

6-Bromo-1,2,3,4-tetrahydroisoquinoline features a bromine substituent at the C6 position of the tetrahydroisoquinoline scaffold, delivering enhanced electrophilicity for downstream functionalization. This bench-stable heterocycle integrates readily into medicinal chemistry libraries and serves as a key intermediate in the synthesis of bioactive alkaloids and CNS-targeted compounds.

Application

6-Bromo-1,2,3,4-tetrahydroisoquinoline serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the aromatic ring via palladium-catalyzed cross-coupling reactions. Its bromine substituent offers high reactivity in Suzuki, Stille, and Negishi couplings, while the tetrahydroisoquinoline core provides structural rigidity and favorable pharmacophoric properties. The compound exhibits excellent bench stability and is readily purified by distillation or chromatography, facilitating integration into multi-step syntheses of bioactive molecules and heterocyclic scaffolds.

Synthesis

  • Route1
    • 6-Bromo-2-(trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline|CS-D0108
      252331-63-8
    • 1-(8-Bromo-3,4-dihydro-1H-isoquinolin-2-yl)-2,2,2-trifluoroethanone|CS-0766889
      726136-49-8
    • ~49%
    • In-stock
      6-Bromo-1,2,3,4-tetrahydroisoquinoline|CS-W019599
      226942-29-6
    • In-stock
      8-Bromo-1,2,3,4-tetrahydroisoquinoline|CS-W005890
      75416-51-2

    References

    • WO2008/76954 A2, ; Page/Page column 50 ; WO 2008/076954 A2
  • Route2

    References

    • US5977134 A1, ; US 5977134 A
  • Route3

    References

    • WO2013/80222 A1, ; Page/Page column 39 ;

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

Quality Control

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Computational Chemistry Data

  • TPSA   12.03
  • LogP   2.0948
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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