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6-Bromohexanenitrile

  • CAS No. 6621-59-6

  • Cat. No. CS-0158396
  • Purity≥95%
  • MDL No.MFCD00013834

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

6-Bromohexanenitrile|CS-0158396

Structure of 6621-59-6

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General Information

  • CAS No. 6621-59-6
  • Cat. No. CS-0158396
  • Purity ≥95%
  • MDL No. MFCD00013834
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₁₀BrN
  • Molecular Weight 176.06
  • Synonym(s) None
  • SMILES N#CCCCCCBr

Description

6-Bromohexanenitrile features a terminal nitrile group flanked by a bromine-substituted alkyl chain, enabling direct functionalization in nucleophilic substitution and cross-coupling reactions. This bifunctional scaffold supports the synthesis of complex amides, heterocycles, and bioactive intermediates under standard conditions.

Application

6-Bromohexanenitrile serves as a versatile bifunctional building block for synthetic organic chemistry, enabling efficient access to γ- and δ-functionalized nitriles. The bromide and nitrile groups exhibit orthogonal reactivity, facilitating palladium-catalyzed cross-coupling reactions and nucleophilic transformations under mild conditions. Its bench-stable nature and compatibility with diverse functional groups support scalable synthesis of complex intermediates, including heterocyclic scaffolds and bioactive molecule precursors.

Synthesis

  • Route1

    References

    • Hanada, Shiori; Motoyama, Yukihiro; Nagashima, Hideo European Journal of Organic Chemistry, 2008 , # 24 p. 4097 - 4100
  • Route2
    • null|null
      111-24-0
    • null|null
      151-50-8
    • ~33%
    • In-stock
      6-Bromohexanenitrile|CS-0158396
      6621-59-6

    References

    • Yasui, Kengo; Fugami, Keigo; Tanaka, Shuji; Tamaru, Yoshinao Journal of Organic Chemistry, 1995 , vol. 60, # 5 p. 1365 - 1380
  • Route3

    References

    • Journal of the American Chemical Society, , vol. 67, p. 687

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   23.79
  • LogP   2.46528
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   4

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