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CS-W001157 4
Total: USD 88.00

4-Iodo-2-methylpyridine

  • CAS No. 22282-65-1

  • Cat. No. CS-W018720
  • Purity≥97%
  • MDL No.MFCD09702484

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

4-Iodo-2-methylpyridine|CS-W018720

Structure of 22282-65-1

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General Information

  • CAS No. 22282-65-1
  • Cat. No. CS-W018720
  • Purity ≥97%
  • MDL No. MFCD09702484
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆IN
  • Molecular Weight 219.02
  • Synonym(s) 4-iodanyl-2-methyl-pyridine
  • SMILES CC1=NC=CC(I)=C1

Description

4-Iodo-2-methylpyridine features a strategically positioned iodine atom at the pyridine ring's 4-position, enabling efficient cross-coupling reactions. The ortho-methyl group enhances electronic modulation and provides steric differentiation, improving selectivity in transition metal-catalyzed transformations. This bench-stable derivative serves as a key intermediate in synthesizing functionalized heterocycles for medicinal chemistry and materials science applications.

Application

4-Iodo-2-methylpyridine serves as a versatile building block in cross-coupling chemistry, enabling efficient access to substituted pyridines via palladium-catalyzed reactions. The iodide group provides high reactivity in Suzuki, Stille, and Negishi couplings, while the methyl substituent offers moderate electronic modulation. Bench-stable and readily purified by distillation, it functions effectively in late-stage functionalization and heterocyclic scaffold construction for medicinal chemistry and materials applications.

Synthesis

  • Route1

    References

    • F. HOFFMANN-LA ROCHE AG Patent: WO2004/80998 A1, 2004 ; Location in patent: Page 27 ; WO 2004/080998 A1
  • Route2
    • null|null
      565237-08-3
    • null|null
      75-36-5
    • ~22%
    • In-stock
      4-Iodo-2-methylpyridine|CS-W018720
      22282-65-1
    • (4-Iodopyridin-2-yl)methyl acetate|CS-1169138
      565237-07-2

    References

    • WO2005/12323 A2, ; Page/Page column 45 ; WO 2005/012323 A2
  • Route3
    • null|null
      79534-90-0
    • ~78%
    • In-stock
      4-Iodo-2-methylpyridine|CS-W018720
      22282-65-1

    References

    • Yamamoto, Yutaka; Yanagi, Akihiko Heterocycles, 1981 , vol. 16, # 7 p. 1161 - 1164

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   12.89
  • LogP   1.99462
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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