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CS-W001157 4
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tert-Butyl 6-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate

  • CAS No. 893566-74-0

  • Cat. No. CS-W018784
  • Purity≥97%
  • MDL No.MFCD08752228

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

tert-Butyl 6-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate|CS-W018784

Structure of 893566-74-0

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General Information

  • CAS No. 893566-74-0
  • Cat. No. CS-W018784
  • Purity ≥97%
  • MDL No. MFCD08752228
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₈BrNO₂
  • Molecular Weight 312.20
  • Synonym(s) 6-BROMO-3,4-DIHYDRO-1H-ISOQUINOLINE-2-CARBOXYLIC ACID TERT-BUTYL ESTER
  • SMILES CC(C)(C)OC(=O)N1CCC2=C(C1)C=CC(Br)=C2

Description

tert-Butyl 6-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate features a brominated dihydroisoquinoline scaffold with a bench-stable tert-butyl ester handle. This moiety integrates readily into transition-metal-catalyzed coupling reactions, enabling efficient access to functionalized isoquinoline derivatives in medicinal chemistry and natural product synthesis.

Application

tert-Butyl 6-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate serves as a versatile building block for the synthesis of isoquinoline-based scaffolds, enabling efficient late-stage functionalization via palladium-catalyzed cross-coupling reactions. The bromo group at the C6 position exhibits high reactivity in Suzuki, Stille, and Negishi couplings, while the protected carboxylate facilitates selective derivatization. Its bench-stable nature and compatibility with diverse reaction conditions make it well-suited for medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • WO2010/145202 A1, ; Page/Page column 35-36 ; WO 2010/145202 A1
  • Route2

    References

    • WO2013/80222 A1, ; Page/Page column 40 ;
  • Route3

    References

    • WO2009/1128 A1, ; Page/Page column 51 ; WO 2009/001128 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-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   29.54
  • LogP   3.7423
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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