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Methyl 1-chloroisoquinoline-3-carboxylate

  • CAS No. 349552-70-1

  • Cat. No. CS-0089041
  • Molecule weight221.64
  • Purity≥98%
  • MDL No.MFCD09863391

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

Methyl 1-chloroisoquinoline-3-carboxylate|CS-0089041

Structure of 349552-70-1

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General Information

  • CAS No. 349552-70-1
  • Cat. No. CS-0089041
  • Purity ≥98%
  • MDL No. MFCD09863391
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₈ClNO₂
  • Molecular Weight 221.64
  • Synonym(s) 3-Isoquinolinecarboxylic acid, 1-chloro-, methyl ester
  • SMILES O=C(C1=CC2=C(C(Cl)=N1)C=CC=C2)OC

Description

Methyl 1-chloroisoquinoline-3-carboxylate features a chlorinated isoquinoline core with a methyl ester at the 3-position, enabling direct incorporation into heterocyclic scaffolds. The electron-deficient ring system supports transition-metal-catalyzed couplings, while the ester group offers versatility in downstream functionalization. This bench-stable reagent facilitates efficient access to bioactive isoquinoline derivatives under standard conditions.

Application

Methyl 1-chloroisoquinoline-3-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient functionalization at the C-1 position of isoquinoline scaffolds. Its chloro group facilitates palladium-catalyzed cross-coupling reactions, while the ester functionality allows for selective reduction or hydrolysis. The compound exhibits good bench stability and compatibility with common protecting group strategies, making it well-suited for medicinal chemistry campaigns and API intermediate development.

Synthesis

  • Route1

    References

    • Saari, Raimo; Toermae, Jonna-Carita; Nevalainen, Tapio Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 2 p. 939 - 950
  • Route2
    • 1-Oxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid|CS-0317434
      63586-82-3
    • ~%
    • In-stock
      Methyl 1-chloroisoquinoline-3-carboxylate|CS-0089041
      349552-70-1

    References

    • Janin, Yves L.; Roulland, Emmanuel; Beurdeley-Thomas, Arnaud; Decaudin, Didier; Monneret, Claude; Poupon, Marie-France Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 4 p. 529 - 532
  • Route3
    • Methyl 1-oxo-3,4-dihydro-2H-isoquinoline-3-carboxylate|CS-0768289
      23364-15-0
    • ~%
    • In-stock
      Methyl 1-chloroisoquinoline-3-carboxylate|CS-0089041
      349552-70-1

    References

    • Janin, Yves L.; Roulland, Emmanuel; Beurdeley-Thomas, Arnaud; Decaudin, Didier; Monneret, Claude; Poupon, Marie-France Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 4 p. 529 - 532

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   39.19
  • LogP   2.6748
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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