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

  • CAS No. 166591-85-1

  • Cat. No. CS-W003490
  • Purity≥98%
  • MDL No.MFCD08274995

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

2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid|CS-W003490

Structure of 166591-85-1

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General Information

  • CAS No. 166591-85-1
  • Cat. No. CS-W003490
  • Purity ≥98%
  • MDL No. MFCD08274995
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₁₉NO₄
  • Molecular Weight 277.32
  • Synonym(s) 2-N-Boc-1,2,3,4-Tetrahydro-Isoquinoline-1-Carboxylic Acid
  • SMILES CC(C)(OC(N1CCC2=CC=CC=C2C1C(O)=O)=O)C

Description

This tetrahydroisoquinoline derivative features a tert-butoxycarbonyl-protected amine and a carboxylic acid group, enabling direct incorporation into peptide synthesis workflows. The protected nitrogen facilitates efficient coupling reactions, while the electron-rich aromatic core supports diverse functionalization. Bench-stable under standard conditions, it serves as a key building block for bioactive alkaloid analogs and pharmaceutical intermediates.

Application

This compound serves as a versatile building block for the synthesis of isoquinoline-based scaffolds in medicinal chemistry. The tert-butyl carbamate (Boc) group provides excellent stability and orthogonal protection, enabling selective deprotection under mild acidic conditions. The carboxylic acid functionality facilitates direct coupling reactions or derivatization, while the tetrahydroisoquinoline core offers a rigid, pharmacophoric framework relevant to bioactive molecule development. Its bench-stable nature and compatibility with standard peptide and heterocyclic synthesis protocols make it ideal for iterative synthetic workflows.

Synthesis

  • Route1

    References

    • Ho, Bin; Michael Crider; Stables, James P European Journal of Medicinal Chemistry, 2001 , vol. 36, # 3 p. 265 - 286
  • Route2

    References

    • European Journal of Medicinal Chemistry, , vol. 36, # 3 p. 265 - 286
  • Route3
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      1359987-43-1
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    • In-stock
      2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid|CS-W003490
      166591-85-1

    References

    • Journal of Organic Chemistry, , vol. 77, # 5 p. 2159 - 2168

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   2.6055
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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