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CS-W001157 4
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(6-chloro-3-pyridinyl)methanol

  • CAS No. 21543-49-7

  • Cat. No. CS-W002737
  • Purity≥97%
  • MDL No.MFCD01075226

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

(6-chloro-3-pyridinyl)methanol|CS-W002737

Structure of 21543-49-7

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General Information

  • CAS No. 21543-49-7
  • Cat. No. CS-W002737
  • Purity ≥97%
  • MDL No. MFCD01075226
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆ClNO
  • Molecular Weight 143.57
  • Synonym(s) 2-Chloro-5-(hydroxymethyl)pyridine
  • SMILES OCc1ccc(nc1)Cl

Description

2-Chloro-5-hydroxymethylpyridine features a pyridine core functionalized with chlorine at the 2-position and a hydroxymethyl group at the 5-position, enabling direct coupling or derivatization in synthetic workflows. This bifunctional architecture supports efficient incorporation into pharmaceutical intermediates and ligand frameworks, where the hydroxymethyl moiety offers a site for further modification while maintaining compatibility with standard reaction conditions.

Application

2-Chloro-5-hydroxymethylpyridine serves as a versatile building block in medicinal chemistry, enabling site-specific functionalization via the reactive chloro and hydroxymethyl groups. The hydroxymethyl moiety facilitates direct oxidation to carboxylic acid or ether formation, while the chlorine supports palladium-catalyzed cross-coupling reactions. Its bench-stable nature and compatibility with common protecting group strategies make it ideal for constructing heterocyclic scaffolds and API intermediates in multi-step syntheses.

Synthesis

  • Route1

    References

    • Lee, Chi-Lik Ken; Loh, Teck-Peng Organic Letters, 2005 , vol. 7, # 14 p. 2965 - 2967
  • Route2

    References

    • Eisai Co., Ltd. Patent: EP1439175 A1, 2004 ; Location in patent: Page 42-43 ;
  • Route3

    References

    • Lee, Kyo Chul; Chi, Dae Yoon Journal of Organic Chemistry, 1999 , vol. 64, # 23 p. 8576 - 8581

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+P364-P405-P501

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Computational Chemistry Data

  • TPSA   33.12
  • LogP   1.2273
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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