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5-Bromopent-1-yne

  • CAS No. 28077-72-7

  • Cat. No. CS-0147349
  • Purity≥98%
  • MDL No.MFCD02258725

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

5-Bromopent-1-yne|CS-0147349

Structure of 28077-72-7

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General Information

  • CAS No. 28077-72-7
  • Cat. No. CS-0147349
  • Purity ≥98%
  • MDL No. MFCD02258725
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₇Br
  • Molecular Weight 147.01
  • Synonym(s) 5-Bromo-1-pentyne
  • SMILES C#CCCCBr

Description

5-Bromopent-1-yne is a versatile alkynyl halide featuring a terminal alkyne and pendant bromide. This molecule integrates readily into transition-metal-catalyzed coupling reactions, enabling efficient access to functionalized alkynes under standard conditions. The bromine atom serves as a robust electrophilic handle for further diversification.

Application

5-Bromopent-1-yne serves as a versatile building block in synthetic organic chemistry, enabling efficient access to functionalized alkynes through palladium-catalyzed coupling reactions. Its terminal alkyne and bromide functionalities allow for orthogonal transformations, facilitating the construction of complex scaffolds via Sonogashira, Stille, or Suzuki couplings. The compound exhibits good bench stability and is readily purified by distillation, making it well-suited for iterative synthesis workflows in medicinal chemistry and materials science.

Synthesis

  • Route1

    References

    • Julia,M.; Maumy,M. Bulletin de la Societe Chimique de France, 1969 , p. 2427 - 2434
  • Route2
    • Pent-4-yn-1-yl 4-methylbenzenesulfonate|CS-0109787
      77758-50-0
    • ~78%
    • In-stock
      5-Bromopent-1-yne|CS-0147349
      28077-72-7

    References

    • Shi, L.; Narula, C. K.; Mak, K. T.; Kao, L.; Xu, Y.; Heck, R. F. Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 3894 - 3900
  • Route3
    • 4-Pentynyl methanesulfonate|CS-0071382
      68275-03-6
    • ~%
    • In-stock
      5-Bromopent-1-yne|CS-0147349
      28077-72-7

    References

    • Rodriguez Rivero, Marta; Alonso, Ines; Carretero, Juan C. Chemistry - A European Journal, 2004 , vol. 10, # 21 p. 5443 - 5459

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02,GHS07
Signal Word : Danger
UN#: 1993
Class : 3
Packing Group : Ⅲ
Hazard Statements : H225-H315-H319-H335
Precautionary Statements : P210-P233-P240-P241-P242-P243-P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P370+P378-P405-P501

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Computational Chemistry Data

  • TPSA   0
  • LogP   1.7947
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   2

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