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CS-W001157 4
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tert-Butyl (5-(hydroxymethyl)pyridin-2-yl)carbamate

  • CAS No. 169280-83-5

  • Cat. No. CS-W018799
  • Purity≥95%
  • MDL No.MFCD07186264

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

tert-Butyl (5-(hydroxymethyl)pyridin-2-yl)carbamate|CS-W018799

Structure of 169280-83-5

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General Information

  • CAS No. 169280-83-5
  • Cat. No. CS-W018799
  • Purity ≥95%
  • MDL No. MFCD07186264
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₆N₂O₃
  • Molecular Weight 224.26
  • Synonym(s) tert-Butyl[5-(hydroxymethyl)pyridin-2-yl]carbamate
  • SMILES O=C(OC(C)(C)C)NC1=NC=C(CO)C=C1

Description

tert-Butyl (5-(hydroxymethyl)pyridin-2-yl)carbamate delivers a pyridine scaffold with a pendant hydroxymethyl group, enabling downstream functionalization through oxidation or coupling reactions. This bench-stable derivative features enhanced solubility and compatibility in aqueous-organic media, simplifying its integration into multi-step synthetic sequences.

Application

tert-Butyl (5-(hydroxymethyl)pyridin-2-yl)carbamate serves as a versatile pyridine-based building block, enabling selective functionalization at the 5-position. The pendant hydroxymethyl group facilitates oxidation to carboxylic acid, reduction to alcohol, or derivatization via Mitsunobu or esterification reactions. The Boc-protected amine offers stability and orthogonality in multi-step syntheses, while the pyridine scaffold provides a reliable platform for medicinal chemistry campaigns targeting kinase inhibitors and other bioactive heterocycles.

Synthesis

  • Route1
    • Ethyl 6-((tert-butoxycarbonyl)amino)nicotinate|CS-0515477
      169280-82-4
    • ~73%
    • In-stock
      tert-Butyl (5-(hydroxymethyl)pyridin-2-yl)carbamate|CS-W018799
      169280-83-5

    References

    • WO2010/3048 A1, ; Page/Page column 110 ; WO 2010/003048 A1
  • Route2
    • Ethyl 6-[Bis(tert-butoxycarbonyl)amino]nicotinate|CS-0742130
      1089330-72-2
    • ~47%
    • In-stock
      tert-Butyl (5-(hydroxymethyl)pyridin-2-yl)carbamate|CS-W018799
      169280-83-5

    References

    • WO2013/59587 A1, ; Page/Page column 207 ;
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 41, # 4 p. 602 - 617

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

Quality Control

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Computational Chemistry Data

  • TPSA   71.45
  • LogP   1.9209
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   2

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