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CS-W001157 4
Total: USD 88.00

2-Methylthio-5-bromopyridine

  • CAS No. 51933-78-9

  • Cat. No. CS-0007564
  • Purity≥98%
  • MDL No.MFCD03411571

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

2-Methylthio-5-bromopyridine|CS-0007564

Structure of 51933-78-9

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General Information

  • CAS No. 51933-78-9
  • Cat. No. CS-0007564
  • Purity ≥98%
  • MDL No. MFCD03411571
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆BrNS
  • Molecular Weight 204.09
  • Synonym(s) 3-Bromo-6-(methylsulfanyl)pyridine; 5-Bromo-2-(methylthio)pyridine
  • SMILES CSC1=NC=C(Br)C=C1

Description

2-Methylthio-5-bromopyridine features a bromine atom at the 5-position and a methylthio group at the 2-position, creating a highly functionalized pyridine scaffold. This electron-deficient heterocycle serves as a key building block in medicinal chemistry, enabling direct coupling reactions via palladium-catalyzed cross-coupling. The thioether moiety enhances solubility and stability compared to analogous halogenated systems.

Application

2-Methylthio-5-bromopyridine serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its bromine substituent. The methylthio group provides orthogonal reactivity and enhances solubility, facilitating downstream functionalization. Bench-stable and readily purified by column chromatography, it functions effectively in the synthesis of heterocyclic scaffolds and biologically active compounds.

Synthesis

  • Route1
    • In-stock
      2,5-Dibromopyridine|CS-W001991
      624-28-2
    • null|null
      624-92-0
    • ~79%
    • In-stock
      2-Methylthio-5-bromopyridine|CS-0007564
      51933-78-9

    References

    • Wang, Xin; Rabbat, Philippe; O'Shea, Paul; Tillyer, Richard; Grabowski; Reider, Paul J. Tetrahedron Letters, 2000 , vol. 41, # 22 p. 4335 - 4338
  • Route2
    • In-stock
      2,5-Dibromopyridine|CS-W001991
      624-28-2
    • null|null
      5188-07-8
    • ~96%
    • In-stock
      2-Methylthio-5-bromopyridine|CS-0007564
      51933-78-9

    References

    • Daiichi Sankyo Company, Limited Patent: EP2239253 A1, 2010 ; Location in patent: Page/Page column 98 ; EP 2239253 A1
  • Route3

    References

    • Testaferri, Lorenzo; Tiecco, Marcello; Tingoli, Marco; Bartoli, Donatella; Massoli, Alberto Tetrahedron, 1985 , vol. 41, # 7 p. 1373 - 1384

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 1759
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H318
Precautionary Statements : P264-P270-P280-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   12.89
  • LogP   2.566
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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