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CS-W001157 4
Total: USD 88.00

3-Iodo-2-methylbenzonitrile

  • CAS No. 52107-66-1

  • Cat. No. CS-0331895
  • Purity≥98%
  • MDL No.None

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

3-Iodo-2-methylbenzonitrile|CS-0331895

Structure of 52107-66-1

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General Information

  • CAS No. 52107-66-1
  • Cat. No. CS-0331895
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆IN
  • Molecular Weight 243.04
  • Synonym(s) None
  • SMILES CC1=C(C=CC=C1I)C#N

Description

3-Iodo-2-methylbenzonitrile features a sterically hindered aryl iodide paired with an electron-deficient nitrile group, enabling efficient cross-coupling under standard conditions. The ortho-methyl substituent enhances stability and directs regioselective functionalization, while the iodine handle facilitates palladium-catalyzed transformations. This bench-stable intermediate integrates readily into complex molecular architectures.

Application

3-Iodo-2-methylbenzonitrile serves as a versatile building block in medicinal chemistry and cross-coupling synthesis. The iodide group enables reliable Suzuki, Stille, and Negishi coupling reactions, while the nitrile and methyl groups offer orthogonal functionalization potential. Bench-stable and readily purified by column chromatography, it facilitates efficient access to substituted biaryls and heterocyclic scaffolds common in drug discovery programs.

Synthesis

  • Route1
    • null|null
      529-19-1
    • ~6%
    • In-stock
      3-Iodo-2-methylbenzonitrile|CS-0331895
      52107-66-1
    • In-stock
      5-Iodo-2-methylbenzonitrile|CS-0098107
      52107-68-3

    References

    • MITSUBISHI GAS CHEMICAL COMPANY, INC. Patent: EP1595862 A1, 2005 ; Location in patent: Page/Page column 9 ;
  • Route2
    • 3-Amino-2-methylbenzonitrile|CS-0222873
      69022-35-1
    • ~%
    • In-stock
      3-Iodo-2-methylbenzonitrile|CS-0331895
      52107-66-1

    References

    • Gore,P.H. et al. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1973 , p. 2940 - 2948

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362+P364

Quality Control

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Computational Chemistry Data

  • TPSA   23.79
  • LogP   2.4713
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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