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CS-W001157 4
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(1R,2R)-N,N'-Di-p-tosyl-1,2-cyclohexanediamine

  • CAS No. 143585-47-1

  • Cat. No. CS-0093704
  • Molecule weight422.56
  • Purity≥97%
  • MDL No.None

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

(1R,2R)-N,N'-Di-p-tosyl-1,2-cyclohexanediamine|CS-0093704

Structure of 143585-47-1

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General Information

  • CAS No. 143585-47-1
  • Cat. No. CS-0093704
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₀H₂₆N₂O₄S₂
  • Molecular Weight 422.56
  • Synonym(s) 4-methyl-N-[(1R,2R)-2-[(4-methylphenyl)sulfonylamino]cyclohexyl]benzenesulfonamide
  • SMILES CC1=CC=C(S(N[C@H]2[C@H](NS(C3=CC=C(C)C=C3)(=O)=O)CCCC2)(=O)=O)C=C1

Description

This chiral diamine features two p-tosyl groups that enhance solubility and stability while maintaining high enantioselectivity in asymmetric synthesis. The rigid cyclohexane backbone enables precise stereocontrol, making it ideal for catalytic applications requiring defined spatial orientation.

Application

(1R,2R)-N,N'-Di-p-tosyl-1,2-cyclohexanediamine serves as a chiral auxiliary in asymmetric synthesis, enabling high enantioselectivity in C–C and C–heteroatom bond formations. Its rigid cyclohexane backbone and two p-toluenesulfonyl (Ts) groups provide excellent stereocontrol, bench stability, and ease of purification. Widely used in enantioselective alkylations and conjugate additions, it functions as a robust scaffold for constructing complex chiral intermediates with predictable stereochemical outcomes.

Synthesis

  • Route1
    • null|null
      20439-47-8
    • null|null
      98-59-9
    • ~81%
    • In-stock
      (1R,2R)-N,N'-Di-p-tosyl-1,2-cyclohexanediamine|CS-0093704
      143585-47-1

    References

    • Gerlach, Uwe; Haubenreich, Thomas; Huenig, Siegfried Chemische Berichte, 1994 , vol. 127, # 10 p. 1969 - 1980
  • Route2
    • rel-(1R,2S)-Cyclohexane-1,2-diamine dihydrochloride|CS-0271377
      10027-80-2
    • null|null
      98-59-9
    • ~90%
    • In-stock
      (1R,2R)-N,N'-Di-p-tosyl-1,2-cyclohexanediamine|CS-0093704
      143585-47-1

    References

    • Alfonso, Ignacio; Rebolledo, Francisca; Gotor, Vicente Tetrahedron Asymmetry, 1999 , vol. 10, # 2 p. 367 - 374
  • Route3
    • null|null
      176298-50-3
    • ~%
    • In-stock
      (1R,2R)-N,N'-Di-p-tosyl-1,2-cyclohexanediamine|CS-0093704
      143585-47-1

    References

    • Angewandte Chemie, , vol. 108, # 4 p. 449 - 452

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P233-P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   92.34
  • LogP   2.87144
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   6

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