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CS-W001157 4
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Methyl 6-(bromomethyl)picolinate

  • CAS No. 146462-25-1

  • Cat. No. CS-W018689
  • Molecule weight230.06
  • Purity≥97%
  • MDL No.MFCD03265368

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

Methyl 6-(bromomethyl)picolinate|CS-W018689

Structure of 146462-25-1

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General Information

  • CAS No. 146462-25-1
  • Cat. No. CS-W018689
  • Purity ≥97%
  • MDL No. MFCD03265368
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₈BrNO₂
  • Molecular Weight 230.06
  • Synonym(s) methyl 6-(bromomethyl)pyridine-2-carboxylate
  • SMILES O=C(OC)C1=NC(CBr)=CC=C1

Description

Methyl 6-(bromomethyl)picolinate features a bromomethyl group at the 6-position of a picolinate ester, enabling direct functionalization in synthetic transformations. This electrophilic handle facilitates efficient coupling reactions, particularly in palladium-catalyzed cross-couplings and nucleophilic substitutions. The molecule exhibits excellent stability under standard bench conditions and integrates readily into complex molecular architectures.

Application

Methyl 6-(bromomethyl)picolinate serves as a versatile building block for constructing bioactive heterocycles and pharmaceutical intermediates. The bromomethyl group enables efficient nucleophilic substitution, facilitating the introduction of diverse amine- and thiol-based side chains. Its bench-stable nature and compatibility with standard coupling conditions make it well-suited for iterative synthesis workflows in medicinal chemistry and process development.

Synthesis

  • Route1

    References

    • Gillespie, Paul; Goodnow, Robert Alan; Tilley, Jefferson Wright Patent: US2006/122256 A1, 2006 ; Location in patent: Page/Page column 23 ; US 20060122256 A1
  • Route2

    References

    • Zeng, Xianshun; Coquiere, David; Alenda, Aurelie; Garrier, Eva; Prange, Thierry; Li, Yun; Reinaud, Olivia; Jabin, Ivan Chemistry - A European Journal, 2006 , vol. 12, # 24 p. 6393 - 6402
  • Route3

    References

    • Journal of the American Chemical Society, , vol. 134, # 20 p. 8670 - 8683

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 3261
Class : 8
Packing Group : Ⅱ
Hazard Statements : H302+H312+H332-H314
Precautionary Statements : P260-P261-P264-P270-P271-P280-P301+P330+P331-P302+P352-P304+P340-P330-P362+P364-P363-P405-P501

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Computational Chemistry Data

  • TPSA   39.19
  • LogP   1.7631
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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