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CS-W001157 4
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Adamantane-2-carboxylic acid

  • CAS No. 15897-81-1

  • Cat. No. CS-0044104
  • Purity≥97%
  • MDL No.MFCD02738135

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

Adamantane-2-carboxylic acid|CS-0044104

Structure of 15897-81-1

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General Information

  • CAS No. 15897-81-1
  • Cat. No. CS-0044104
  • Purity ≥97%
  • MDL No. MFCD02738135
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₆O₂
  • Molecular Weight 180.24
  • Synonym(s) tricyclo[3.3.1.1~3,7~]decane-2-carboxylate
  • SMILES O=C(O)C1[C@H]2C[C@@H]3C[C@@H](C[C@H]1C3)C2

Description

Adamantane-2-carboxylic acid delivers a rigid, polycyclic scaffold with a pendant carboxylic acid group, enabling robust conjugation in bioconjugation and materials chemistry. The molecule’s high thermal stability and steric bulk support precise molecular design in drug delivery systems and functionalized polymers.

Application

Adamantane-2-carboxylic acid serves as a robust, sterically hindered building block for medicinal chemistry and materials science. Its rigid, diamondoid core imparts metabolic stability and enhanced lipophilicity, while the carboxylic acid group enables facile derivatization via amide, ester, or acyl chloride formation. The compound exhibits excellent bench stability and is readily purified by recrystallization, facilitating its use in multi-step syntheses of bioactive molecules and functionalized polymers.

Synthesis

  • Route1
    • null|null
      39750-93-1
    • ~82%
    • In-stock
      Adamantane-2-carboxylic acid|CS-0044104
      15897-81-1

    References

    • Natarajan, Arunkumar; Joy, Abraham; Kaanumalle, Lakshmi S.; Scheffer, John R.; Ramamurthy Journal of Organic Chemistry, 2002 , vol. 67, # 24 p. 8339 - 8350
  • Route2
    • Adamantane-2-carbonitrile|CS-0100829
      35856-00-9
    • ~98%
    • In-stock
      Adamantane-2-carboxylic acid|CS-0044104
      15897-81-1

    References

    • Frantz, Marie-Celine; Skoda, Erin M.; Sacher, Joshua R.; Epperly, Michael W.; Goff, Julie P.; Greenberger, Joel S.; Wipf, Peter Organic and Biomolecular Chemistry, 2013 , vol. 11, # 25 p. 4147 - 4153
  • Route3

    References

    • Journal of Organic Chemistry, , vol. 47, # 21 p. 4120 - 4128

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-P280-P302+P352

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Computational Chemistry Data

  • TPSA   37.3
  • LogP   2.1433
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   1

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