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CS-W001157 4
Total: USD 88.00

2,6-Dimethylbenzonitrile

  • CAS No. 6575-13-9

  • Cat. No. CS-W011101
  • Purity≥98%
  • MDL No.MFCD00037166

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

2,6-Dimethylbenzonitrile|CS-W011101

Structure of 6575-13-9

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General Information

  • CAS No. 6575-13-9
  • Cat. No. CS-W011101
  • Purity ≥98%
  • MDL No. MFCD00037166
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₉N
  • Molecular Weight 131.18
  • Synonym(s) 2-Cyano-m-xylene
  • SMILES C1=C(C(=C(C=C1)C)C#N)C

Description

2,6-Dimethylbenzonitrile features a nitrile group flanked by two methyl substituents at the 2 and 6 positions of the benzene ring, creating a sterically hindered, electron-deficient aromatic system. This configuration enhances stability and directs electrophilic substitution selectively. The compound serves as a valuable building block in synthetic organic chemistry, particularly for constructing functionalized arenes under mild conditions. Its bench-stable nature facilitates handling in routine laboratory workflows.

Application

2,6-Dimethylbenzonitrile serves as a robust building block in medicinal chemistry and materials science, offering enhanced steric shielding around the nitrile group due to ortho-methyl substitution. Its bench-stable nature, combined with high functional group tolerance, enables reliable use in nucleophilic transformations, transition-metal-catalyzed couplings, and heterocycle synthesis. The aromatic core facilitates efficient purification and crystallization, making it well-suited for scale-up and process development.

Synthesis

  • Route1

    References

    • Synlett, , # 10 p. 1562 - 1566
  • Route2

    References

    • Schareina, Thomas; Zapf, Alexander; Beller, Matthias Chemical Communications, 2004 , # 12 p. 1388 - 1389
  • Route3
    • null|null
      151-50-8
    • In-stock
      2,6-Dimethylphenyl trifluoromethanesulfonate|CS-1244544
      86364-02-5
    • ~84%
    • In-stock
      2,6-Dimethylbenzonitrile|CS-W011101
      6575-13-9

    References

    • Takagi, Kentaro; Sakakibara, Yasumasa Chemistry Letters, 1989 , p. 1957 - 1958

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   23.79
  • LogP   2.17512
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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