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CS-W001157 4
Total: USD 88.00

4-(2-Bromoethyl)benzonitrile

  • CAS No. 72054-56-9

  • Cat. No. CS-W018706
  • Purity≥97%
  • MDL No.MFCD12025077

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

4-(2-Bromoethyl)benzonitrile|CS-W018706

Structure of 72054-56-9

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General Information

  • CAS No. 72054-56-9
  • Cat. No. CS-W018706
  • Purity ≥97%
  • MDL No. MFCD12025077
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₈BrN
  • Molecular Weight 210.07
  • Synonym(s) None
  • SMILES N#CC1=CC=C(C=C1)CCBr

Description

4-(2-Bromoethyl)benzonitrile features a para-substituted benzene ring bearing both a nitrile and a bromoethyl side chain, enabling direct functionalization in cross-coupling and click chemistry. The bromoethyl group provides a reactive handle for nucleophilic substitution, while the nitrile imparts electron-withdrawing character and polarity. This combination facilitates incorporation into advanced synthetic scaffolds and bioconjugation workflows under standard conditions.

Application

4-(2-Bromoethyl)benzonitrile serves as a versatile bifunctional building block for C–C and C–N coupling reactions, enabling efficient construction of aryl-alkyl linkages. The bromoethyl side chain facilitates palladium-catalyzed cross-coupling, while the nitrile group offers compatibility with nucleophilic additions and subsequent transformations into amides or carboxylic acids. Its bench-stable crystalline form and predictable reactivity make it ideal for modular synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • 4-(2-Bromoethyl)benzaldehyde|CS-0317201
      7617-70-1
    • ~72%
    • In-stock
      4-(2-Bromoethyl)benzonitrile|CS-W018706
      72054-56-9

    References

    • Bartel, Stephan; Hahn, Michael; Moradi, Wahed Ahmed; Becker, Eva-Maria; Roelle, Thomas; Stasch, Johannes-Peter; Schlemmer, Karl-Heinz; Wunder, Frank; Knorr, Andreas; Lang, Dieter Patent: US2010/29772 A1, 2010 ; Location in patent: Page/Page column 15 ;
  • Route2

    References

    • Wagner, G.; Vieweg, H. Pharmazie, 1982 , vol. 37, # 1 p. 13 - 16
  • Route3

    References

    • Pharmazie, , vol. 37, # 1 p. 13 - 16

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 3261
Class : 8
Packing Group : Ⅱ
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   2.49568
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   2

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