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CS-W001157 4
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(1R,2R)-Cyclohexane-1,2-dicarboxylic Acid

  • CAS No. 46022-05-3

  • Cat. No. CS-0031455
  • Purity≥97%
  • MDL No.MFCD00062973

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

(1R,2R)-Cyclohexane-1,2-dicarboxylic Acid|CS-0031455

Structure of 46022-05-3

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General Information

  • CAS No. 46022-05-3
  • Cat. No. CS-0031455
  • Purity ≥97%
  • MDL No. MFCD00062973
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₂O₄
  • Molecular Weight 172.18
  • Synonym(s) (R,R)-1,2-Cyclohexanedicarboxylic acid
  • SMILES C(O)(=O)[C@H]1[C@H](C(O)=O)CCCC1

Description

(1R,2R)-Cyclohexane-1,2-dicarboxylic acid features a rigid, chiral cyclohexane backbone with carboxylic acid groups in a cis-1,2 configuration. This stereochemistry imparts high diastereoselectivity in asymmetric synthesis, enabling precise control in the construction of complex molecular architectures. The molecule's defined spatial orientation enhances reproducibility in catalytic and polymerization reactions.

Application

(1R,2R)-Cyclohexane-1,2-dicarboxylic acid serves as a chiral building block for asymmetric synthesis, enabling stereoselective transformations in natural product and pharmaceutical development. Its rigid cyclohexane backbone provides defined spatial orientation for diastereoselective functionalization, while the carboxylic acid groups offer versatile handles for derivatization, amide formation, or salt generation. Bench-stable and readily purified by recrystallization, it functions effectively in standard coupling and cyclization protocols.

Synthesis

  • Route1
    • null|null
      3886-69-9
    • rel-1,2-Cyclohexanedicarboxylic acid|CS-0653459
      2305-32-0
    • ~%
    • In-stock
      (1R,2R)-Cyclohexane-1,2-dicarboxylic Acid|CS-0031455
      46022-05-3

    References

    • CADILA HEALTHCARE LIMITED; DWIVEDI, Shri Prakash Dhar; SINGH, Ramesh Chandra; CHAVDA, Rajendra Gokalbhai Patent: WO2013/121440 A1, 2013 ; Location in patent: Page/Page column 26; 27 ;
  • Route2
    • null|null
      1292320-69-4
    • ~%
    • In-stock
      (1R,2R)-Cyclohexane-1,2-dicarboxylic Acid|CS-0031455
      46022-05-3

    References

    • Malihi, Farzad; Clive, Derrick L. J.; Chang, Che-Chien; Minaruzzaman Journal of Organic Chemistry, 2013 , vol. 78, # 3 p. 996 - 1013
  • Route3
    • rel-1,2-Cyclohexanedicarboxylic acid|CS-0653459
      2305-32-0
    • ~%
    • In-stock
      (1R,2R)-Cyclohexane-1,2-dicarboxylic Acid|CS-0031455
      46022-05-3

    References

    • RANBAXY LABORATORIES LIMITED; JAYACHANDRA, Suresh, Babu; GAHLOT, Udaibhan, Singh; SINGH, Tarun, Kumar; KHANDURI, Chandra, Has Patent: WO2012/131606 A1, 2012 ;

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

Quality Control

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Computational Chemistry Data

  • TPSA   74.6
  • LogP   0.962
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   2

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