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CS-W001157 4
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1-(Boc-Amino)cyclopropanecarboxylic acid

  • CAS No. 88950-64-5

  • Cat. No. CS-W002346
  • Purity≥97%
  • MDL No.MFCD00083257

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

1-(Boc-Amino)cyclopropanecarboxylic acid|CS-W002346

Structure of 88950-64-5

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General Information

  • CAS No. 88950-64-5
  • Cat. No. CS-W002346
  • Purity ≥97%
  • MDL No. MFCD00083257
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₅NO₄
  • Molecular Weight 201.22
  • Synonym(s) BOC-1-Amino-1-cyclopropanecarboxylic acid
  • SMILES O=C(NC1(CC1)C(=O)O)OC(C)(C)C

Description

1-(Boc-Amino)cyclopropanecarboxylic acid features a sterically constrained cyclopropane ring paired with a bench-stable Boc-protected amine, enabling direct incorporation into peptide chains. The rigid scaffold imparts conformational control, while the carboxylic acid group facilitates coupling reactions under standard conditions. This derivative serves as a key building block for bioactive peptidomimetics and cyclic peptide synthesis.

Application

1-(Boc-Amino)cyclopropanecarboxylic acid serves as a versatile building block for the synthesis of cyclopropyl-containing peptidomimetics and bioactive scaffolds. The Boc-protected amine enables orthogonal handling in peptide coupling workflows, while the cyclopropanecarboxylic acid moiety provides structural rigidity and metabolic stability. This compound exhibits excellent bench stability, facilitates straightforward purification, and participates reliably in standard amidation, reduction, and functionalization reactions under mild conditions.

Synthesis

  • Route1

    References

    • Khalil, Ehab M.; Subasinghe, Nalin L.; Johnson, Rodney L. Tetrahedron Letters, 1996 , vol. 37, # 20 p. 3441 - 3444
  • Route2

    References

    • Journal of Organic Chemistry, , vol. 67, # 11 p. 3965 - 3968
  • Route3

    References

    • Pearson-Long, Morwenna S.M.; Beauseigneur, Alice; Karoyan, Philippe; Szymoniak, Jan; Bertus, Philippe Synthesis, 2010 , # 20 art. no. T13410SS, p. 3410 - 3414

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-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   75.63
  • LogP   1.1283
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   2

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