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CS-W001157 4
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2-(o-Tolyl)acetonitrile

  • CAS No. 22364-68-7

  • Cat. No. CS-W019570
  • Purity≥98%
  • MDL No.MFCD00001904

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

2-(o-Tolyl)acetonitrile|CS-W019570

Structure of 22364-68-7

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General Information

  • CAS No. 22364-68-7
  • Cat. No. CS-W019570
  • Purity ≥98%
  • MDL No. MFCD00001904
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₉N
  • Molecular Weight 131.17
  • Synonym(s) Tolylacetonitrile
  • SMILES N#CCC1=CC=CC=C1C

Description

2-(o-Tolyl)acetonitrile features a benzene ring substituted with both a methyl group and a nitrile-bearing acetyl side chain, delivering a sterically constrained, electron-deficient aryl moiety. This configuration enables efficient coupling in transition metal-catalyzed reactions and serves as a robust building block for heterocyclic synthesis under standard conditions.

Application

2-(o-Tolyl)acetonitrile serves as a versatile building block in synthetic organic chemistry, enabling efficient construction of heterocyclic scaffolds and functionalized aryl derivatives. Its ortho-tolyl group provides steric and electronic modulation, while the nitrile functionality facilitates nucleophilic addition, cyclization, and transition-metal-catalyzed transformations. The compound exhibits good bench stability and is compatible with standard purification methods, making it well-suited for use in medicinal chemistry campaigns and process development workflows.

Synthesis

  • Route1
    • null|null
      143-33-9
    • null|null
      552-45-4
    • ~98%
    • In-stock
      2-(o-Tolyl)acetonitrile|CS-W019570
      22364-68-7

    References

    • Showa Denko K.K. Patent: US6372921 B1, 2002 ; Location in patent: Example 7 ;
  • Route2
    • In-stock
      2-(Trimethylsilyl)acetonitrile|CS-0120673
      18293-53-3
    • null|null
      95-46-5
    • ~83%
    • In-stock
      2-(o-Tolyl)acetonitrile|CS-W019570
      22364-68-7

    References

    • Wu, Lingyun; Hartwig, John F. Journal of the American Chemical Society, 2005 , vol. 127, # 45 p. 15824 - 15832
  • Route3
    • null|null
      84109-17-1
    • null|null
      590-17-0
    • ~92%
    • In-stock
      2,2'-Dimethyl-1,1'-biphenyl|CS-0152961
      605-39-0
    • In-stock
      2-(o-Tolyl)acetonitrile|CS-W019570
      22364-68-7

    References

    • Frejd, Torbjoern; Klingstedt, Tomas Synthesis, 1987 , # 1 p. 40 - 42

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 3276
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H302+H312-H315-H319-H331-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P361+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   23.79
  • LogP   2.0611
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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