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CS-W001157 4
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5-Iodo-2-methylbenzonitrile

  • CAS No. 52107-68-3

  • Cat. No. CS-0098107
  • Purity≥98%
  • MDL No.MFCD00128256

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

5-Iodo-2-methylbenzonitrile|CS-0098107

Structure of 52107-68-3

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General Information

  • CAS No. 52107-68-3
  • Cat. No. CS-0098107
  • Purity ≥98%
  • MDL No. MFCD00128256
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆IN
  • Molecular Weight 243.04
  • Synonym(s) 5-iodo-2-methylbenzenecarbonitrile
  • SMILES N#CC1=CC(I)=CC=C1C

Description

5-Iodo-2-methylbenzonitrile features a sterically hindered aromatic core with complementary electron-withdrawing nitrile and iodine substituents. This combination enables efficient cross-coupling transformations under standard conditions, delivering functionalized heterocycles with high regiocontrol. The bench-stable compound integrates readily into synthetic sequences requiring halogen-directed C–C bond formation.

Application

5-Iodo-2-methylbenzonitrile serves as a versatile building block in cross-coupling chemistry, enabling efficient Suzuki and Stille reactions due to its stable aryl iodide functionality and electron-withdrawing nitrile group. The methyl substituent provides steric and electronic modulation, enhancing regioselectivity in subsequent transformations. Its bench-stable nature and compatibility with standard catalytic systems make it ideal for constructing complex heterocycles and pharmaceutical scaffolds.

Synthesis

  • Route1

    References

    • Yestrepsky, Bryan D.; Kretz, Colin A.; Xu, Yuanxi; Holmes, Autumn; Sun, Hongmin; Ginsburg, David; Larsen, Scott D. Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 6 p. 1538 - 1544
  • Route2
    • null|null
      529-19-1
    • ~69%
    • 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 ;

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

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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