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CS-W001157 4
Total: USD 88.00

1-(Bromomethyl)adamantane

  • CAS No. 14651-42-4

  • Cat. No. CS-0044357
  • Molecule weight229.16
  • Purity≥98%
  • MDL No.MFCD00185303

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

1-(Bromomethyl)adamantane|CS-0044357

Structure of 14651-42-4

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General Information

  • CAS No. 14651-42-4
  • Cat. No. CS-0044357
  • Purity ≥98%
  • MDL No. MFCD00185303
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₇Br
  • Molecular Weight 229.16
  • Synonym(s) AKOS BBS-00006961
  • SMILES BrCC12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3

Description

1-(Bromomethyl)adamantane delivers a rigid, sterically hindered alkylating handle ideal for constructing functionalized molecular architectures. The bromomethyl group enables efficient nucleophilic substitution under mild conditions, while the adamantane scaffold imparts exceptional thermal and chemical stability. This combination ensures reliable reactivity in complex synthesis workflows.

Application

1-(Bromomethyl)adamantane serves as a robust, sterically hindered alkylating agent enabling efficient functionalization of nucleophiles under mild conditions. Its adamantyl framework imparts exceptional bench stability and resistance to decomposition, while the primary bromide functionality facilitates reliable coupling in SN2 reactions. Widely employed in medicinal chemistry and materials science, it functions as a key building block for constructing rigid, three-dimensional scaffolds and bioactive molecules with enhanced metabolic stability.

Synthesis

  • Route1

    References

    • Bochmann, Manfred; Wilkinson, Geoffrey; Young, Brent G. Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1980 , p. 1879 - 1887
  • Route2

    References

    • Journal of the American Chemical Society, , vol. 88, # 19 p. 4475 - 4484
  • Route3
    • In-stock
      3-(Hydroxymethyl)adamantane|CS-W020560
      770-71-8
    • ~%
    • In-stock
      1-(Bromomethyl)adamantane|CS-0044357
      14651-42-4
    • null|null
      14504-84-8

    References

    • Journal of the American Chemical Society, , vol. 104, # 12 p. 3481 - 3487

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   0
  • LogP   3.5977
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   1

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