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CS-W001157 4
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2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

  • CAS No. 170097-67-3

  • Cat. No. CS-W005911
  • Purity≥98%
  • MDL No.MFCD05861548

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

2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid|CS-W005911

Structure of 170097-67-3

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General Information

  • CAS No. 170097-67-3
  • Cat. No. CS-W005911
  • Purity ≥98%
  • MDL No. MFCD05861548
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₁₉NO₄
  • Molecular Weight 277.32
  • Synonym(s) N-Boc-6-Hydroxycarbonyl-1,2,3,4-Tetrahydroisoquinoline
  • SMILES CC(C)(C)OC(=O)N1CCC2=CC(=CC=C2C1)C(O)=O

Description

This tetrahydroisoquinoline derivative features a tert-butoxycarbonyl-protected amine and a carboxylic acid group at the 6-position, enabling direct incorporation into peptide conjugates or heterocyclic scaffolds. The Boc group ensures stability during synthesis, while the electron-rich aromatic core facilitates transition metal-catalyzed coupling reactions under standard conditions.

Application

2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid serves as a versatile building block for the synthesis of tetrahydroisoquinoline-based scaffolds. The tert-butoxycarbonyl group provides robust protection of the amine, enabling stable handling and compatibility with diverse coupling reactions. The carboxylic acid functionality facilitates efficient derivatization and conjugation, supporting applications in medicinal chemistry and peptide synthesis. Its structural integrity and functional group orthogonality make it a reliable intermediate in multi-step synthetic sequences.

Synthesis

  • Route1

    References

    • Haginoya, Noriyasu; Kobayashi, Syozo; Komoriya, Satoshi; Yoshino, Toshiharu; Suzuki, Makoto; Shimada, Takashi; Watanabe, Kengo; Hirokawa, Yumiko; Furugori, Taketoshi; Nagahara, Takayasu Journal of Medicinal Chemistry, 2004 , vol. 47, # 21 p. 5167 - 5182
  • Route2

    References

    • Journal of Medicinal Chemistry, , vol. 47, # 21 p. 5167 - 5182
  • Route3
    • 1,2,3,4-Tetrahydroisoquinolin-6-ol hydrochloride|CS-0669062
      63905-73-7
    • ~%
    • In-stock
      2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid|CS-W005911
      170097-67-3

    References

    • Journal of Medicinal Chemistry, , vol. 47, # 21 p. 5167 - 5182

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   66.84
  • LogP   2.678
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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