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CS-W001157 4
Total: USD 88.00

(1R,2S)-rel-Cyclopropane-1,2-dicarboxylic acid

  • CAS No. 696-74-2

  • Cat. No. CS-0053628
  • Purity≥97%
  • MDL No.MFCD00185863

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

(1R,2S)-rel-Cyclopropane-1,2-dicarboxylic acid|CS-0053628

Structure of 696-74-2

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General Information

  • CAS No. 696-74-2
  • Cat. No. CS-0053628
  • Purity ≥97%
  • MDL No. MFCD00185863
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₆O₄
  • Molecular Weight 130.10
  • Synonym(s) cis-1,2-Cyclopropane dicarboxylic acid
  • SMILES OC(=O)[C@H]1C[C@H]1C(O)=O

Description

This chiral cyclopropane derivative features a rigid, strained ring system with two adjacent carboxylic acid groups. The (1R,2S)-rel configuration imparts defined stereochemistry essential for asymmetric synthesis and molecular recognition studies. Bench-stable and moisture-tolerant, it serves as a valuable scaffold in medicinal chemistry and catalyst design.

Application

(1R,2S)-rel-Cyclopropane-1,2-dicarboxylic acid serves as a valuable chiral building block in synthetic organic chemistry, enabling stereoselective transformations through its rigid cyclopropane framework. The molecule's defined stereochemistry and orthogonal carboxylic acid functionality facilitate efficient derivatization, including amidation and esterification, with high diastereoselectivity. Its bench-stable crystalline form simplifies handling and purification, making it well-suited for use in medicinal chemistry campaigns and the construction of biologically relevant heterocyclic scaffolds.

Synthesis

  • Route1

    References

    • Csuk, Rene; Von Scholz, Yvonne Tetrahedron, 1995 , vol. 51, # 26 p. 7193 - 7206
  • Route2

    References

    • Ashton; Canning Meurer; Cantone; Field; Hannah; Karkas; Liou; Patel; Perry; Wagner; Walton; Tolman Journal of Medicinal Chemistry, 1988 , vol. 31, # 12 p. 2304 - 2315
  • Route3

    References

    • Neumeyer, John L.; Zhang, Ao; Xiong, Wennan; Gu, Xiao-Hui; Hilbert, James E.; Knapp, Brian I.; Negus, S. Stevens; Mello, Nancy K.; Bidlack, Jean M. Journal of Medicinal Chemistry, 2003 , vol. 46, # 24 p. 5162 - 5170

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 3261
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H315-H318-H335
Precautionary Statements : P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P363-P405-P501

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Computational Chemistry Data

  • TPSA   74.6
  • LogP   -0.2083
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   2

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