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CS-W001157 4
Total: USD 88.00

4-((Dimethylamino)methyl)benzonitrile

  • CAS No. 35525-86-1

  • Cat. No. CS-0151296
  • Purity≥98%
  • MDL No.MFCD00029578

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

4-((Dimethylamino)methyl)benzonitrile|CS-0151296

Structure of 35525-86-1

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General Information

  • CAS No. 35525-86-1
  • Cat. No. CS-0151296
  • Purity ≥98%
  • MDL No. MFCD00029578
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₂N₂
  • Molecular Weight 160.22
  • Synonym(s) Benzonitrile,4-[(diMethylaMino)Methyl]-
  • SMILES CN(C)CC1=CC=C(C=C1)C#N

Description

4-((Dimethylamino)methyl)benzonitrile features a para-substituted benzene ring bearing a dimethylaminomethyl group and a nitrile moiety. This electron-rich aryl scaffold integrates readily into synthetic routes requiring polar, basic sites adjacent to aromatic systems. The nitrile enhances reactivity in nucleophilic transformations, while the dimethylamino group provides tunable basicity and solubility across organic media.

Application

4-((Dimethylamino)methyl)benzonitrile serves as a versatile building block in medicinal chemistry, enabling the construction of bioactive heterocycles and pharmaceutical scaffolds. Its nitrile group facilitates nucleophilic addition and cyclization reactions, while the dimethylaminomethyl moiety offers a handle for functional diversification via alkylation or reductive amination. The compound exhibits excellent bench stability and compatibility with standard synthetic protocols, simplifying purification and scale-up in multi-step syntheses.

Synthesis

  • Route1
    • 4-Cyano-N,N-dimethylbenzamide|CS-0516609
      24167-50-8
    • ~85%
    • In-stock
      4-((Dimethylamino)methyl)benzonitrile|CS-0151296
      35525-86-1

    References

    • Hanada, Shiori; Tsutsumi, Emi; Motoyama, Yukihiro; Nagashima, Hideo Journal of the American Chemical Society, 2009 , vol. 131, # 41 p. 15032 - 15040
  • Route2
    • null|null
      124-40-3
    • In-stock
      4-Cyanobenzyl Bromide|CS-W001931
      17201-43-3
    • ~96%
    • In-stock
      4-((Dimethylamino)methyl)benzonitrile|CS-0151296
      35525-86-1

    References

    • Tayama, Eiji; Kimura, Hiroshi Angewandte Chemie - International Edition, 2007 , vol. 46, # 46 p. 8869 - 8871
  • Route3
    • null|null
      121-44-8
    • In-stock
      4-Cyanobenzyl Bromide|CS-W001931
      17201-43-3
    • ~99%
    • In-stock
      4-((Dimethylamino)methyl)benzonitrile|CS-0151296
      35525-86-1

    References

    • Boehringer Ingelheim Pharma GmbH and Co.KG Patent: EP1206446 B1, 2004 ; Location in patent: Page 18-19 ;

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   27.03
  • LogP   1.61988
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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