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CS-W001157 4
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(S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol

  • CAS No. 18881-17-9

  • Cat. No. CS-W014288
  • Purity≥97%
  • MDL No.MFCD01631316

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

(S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol|CS-W014288

Structure of 18881-17-9

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General Information

  • CAS No. 18881-17-9
  • Cat. No. CS-W014288
  • Purity ≥97%
  • MDL No. MFCD01631316
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₃NO
  • Molecular Weight 163.22
  • Synonym(s) (S)-3-Hydroxymethyl-1,2,3,4-tetrahydroisoquinoline
  • SMILES OC[C@H]1NCC2=C(C=CC=C2)C1

Description

(S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol features a chiral tetrahydroisoquinoline scaffold with a primary alcohol at the 3-position, offering a versatile handle for conjugation. This bench-stable, moisture-tolerant building block integrates readily into bioactive molecule synthesis, particularly in alkaloid and CNS-targeted compound development.

Application

(S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol serves as a versatile chiral building block in medicinal chemistry, enabling the synthesis of bioactive isoquinoline derivatives. Its pendant alcohol group facilitates derivatization via esterification, etherification, or oxidation to aldehyde, while maintaining stereochemical integrity. The tetrahydroisoquinoline core provides structural rigidity and favorable pharmacophoric properties relevant to CNS-targeted compounds. Bench-stable and readily purified by chromatography, it functions efficiently in standard coupling and functional group interconversion protocols.

Synthesis

  • Route1
    • null|null
      79815-19-3
    • ~65%
    • In-stock
      (S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol|CS-W014288
      18881-17-9

    References

    • Chelopo, Madichaba P.; Pawar, Sachin A.; Sokhela, Mxolisi K.; Govender, Thavendran; Kruger, Hendrik G.; Maguire, Glenn E. M. European Journal of Medicinal Chemistry, 2013 , vol. 66, p. 407 - 414
  • Route2

    References

    • Astra AB Patent: US6034097 A1, 2000 ; US 6034097 A
  • Route3
    • L-Porretine Quinapril Impurity|CS-0229751
      74163-81-8
    • ~98%
    • In-stock
      (S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol|CS-W014288
      18881-17-9

    References

    • Aggarwal, Varinder K.; Humphries, Paul S.; Fenwick, Ashley Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 20 p. 2883 - 2889

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   32.26
  • LogP   0.6932
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   1

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