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CS-W001157 4
Total: USD 88.00

6-Bromo-2-methylpyridin-3-ol

  • CAS No. 118399-86-3

  • Cat. No. CS-W018789
  • Purity≥97%
  • MDL No.MFCD11044277

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

6-Bromo-2-methylpyridin-3-ol|CS-W018789

Structure of 118399-86-3

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General Information

  • CAS No. 118399-86-3
  • Cat. No. CS-W018789
  • Purity ≥97%
  • MDL No. MFCD11044277
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆BrNO
  • Molecular Weight 188.02
  • Synonym(s) 6-Bromo-3-hydroxy-2-methylpyridine
  • SMILES OC1=CC=C(Br)N=C1C

Description

6-Bromo-2-methylpyridin-3-ol features a brominated pyridinol scaffold with strategic substitution at the 6-position and a methyl group at the 2-position, enabling direct functionalization in cross-coupling and cyclization reactions. The phenolic hydroxyl offers hydrogen-bonding capacity and facilitates derivatization, while the electron-deficient ring enhances reactivity toward nucleophiles. This bench-stable compound serves as a key intermediate in medicinal chemistry and agrochemical synthesis.

Application

6-Bromo-2-methylpyridin-3-ol serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the pyridine ring via palladium-catalyzed cross-coupling reactions. The bromo group facilitates Suzuki, Stille, and Negishi couplings, while the phenolic hydroxyl supports derivatization or metal complexation. Bench-stable and compatible with common protecting group strategies, it functions reliably in multi-step syntheses of heterocyclic scaffolds and API intermediates.

Synthesis

  • Route1

    References

    • Hadida Ruah, Sara Sabina; Kallel, Edward Adam; Miller, Mark Thomas; Arumugam, Vijayalaksmi; McCartney, Jason; Anderson, Corey; Grootenhuis, Peter Diederik Jan; Jiang, Licong Patent: US2012/196869 A1, 2012 ; Location in patent: Paragraph 0338; 0339 ; US 20120196869 A1
  • Route2

    References

    • Klumpp, Cedric; Burger, Alain; Mislin, Gaetan L.; Abdallah, Mohamed A. Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 6 p. 1721 - 1724
  • Route3

    References

    • Synlett, , # 11 p. 1678 - 1682

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

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Computational Chemistry Data

  • TPSA   33.12
  • LogP   1.85812
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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