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(1R,2R)-N1,N2-Dimethyl-1,2-bis(3-(trifluoromethyl)phenyl)ethane-1,2-diamine

  • CAS No. 137944-39-9

  • Cat. No. CS-0182501
  • Purity≥98%
  • MDL No.None

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

(1R,2R)-N1,N2-Dimethyl-1,2-bis(3-(trifluoromethyl)phenyl)ethane-1,2-diamine|CS-0182501

Structure of 137944-39-9

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General Information

  • CAS No. 137944-39-9
  • Cat. No. CS-0182501
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₁₈F₆N₂
  • Molecular Weight 376.34
  • Synonym(s) (1R,2R)-(+)-N,N'-Dimethyl-1,2-bis[3-(trifluoromethyl)phenyl]ethylenediamine
  • SMILES CN[C@@H]([C@H](NC)C1=CC(C(F)(F)F)=CC=C1)C2=CC(C(F)(F)F)=CC=C2

Description

This chiral diamine features two trifluoromethyl-substituted phenyl rings flanking a rigid ethane backbone, delivering enhanced electron-withdrawing character and steric bulk. The (1R,2R) stereochemistry ensures high enantioselectivity in asymmetric catalysis, while the dimethylated nitrogen atoms improve solubility and stability under standard reaction conditions.

Application

(1R,2R)-N1,N2-Dimethyl-1,2-bis(3-(trifluoromethyl)phenyl)ethane-1,2-diamine serves as a chiral diamine ligand in transition-metal-catalyzed asymmetric transformations. Its rigid, sterically defined structure—derived from 3-(trifluoromethyl)phenyl groups—enables precise stereocontrol in palladium- and copper-catalyzed reactions. The dimethyl substitution enhances solubility and bench stability, while the trifluoromethyl moieties contribute to electronic modulation and improved functional group tolerance in synthesis workflows.

Synthesis

  • Route1
    • null|null
      121372-62-1
    • ~%
    • In-stock
      (1R,2R)-N1,N2-Dimethyl-1,2-bis(3-(trifluoromethyl)phenyl)ethane-1,2-diamine|CS-0182501
      137944-39-9

    References

    • Journal of Organic Chemistry, , vol. 54, # 10 p. 2420 - 2425
  • Route2
    • In-stock
      (1R,2R)-N1,N2-Dimethyl-1,2-bis(3-(trifluoromethyl)phenyl)ethane-1,2-diamine|CS-0182501
      137944-39-9
    • ~%
    • In-stock
      (1R,2R)-N1,N2-Dimethyl-1,2-bis(3-(trifluoromethyl)phenyl)ethane-1,2-diamine|CS-0182501
      137944-39-9

    References

    • Journal of Organic Chemistry, , vol. 54, # 10 p. 2420 - 2425
  • Route3

    References

    • Journal of Organic Chemistry, , vol. 54, # 10 p. 2420 - 2425

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS09
Signal Word : Warning
UN#: 3077
Class : 9
Packing Group : Ⅲ
Hazard Statements : H410
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   24.06
  • LogP   4.9454
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   5

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