(1R,2R)-N,N'-Di-p-tosyl-1,2-diphenyl-1,2-ethylenediamine

Name: (1R,2R)-N,N'-Di-p-tosyl-1,2-diphenyl-1,2-ethylenediamine
Brand: ChemScene
Availability: InStock
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CAS No. 121758-19-8
Cat. No. CS-0093700
Molecule weight520.66
Purity≥98%
MDL No.MFCD00269673

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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(1R,2R)-N,N'-Di-p-tosyl-1,2-diphenyl-1,2-ethylenediamine|CS-0093700

Structure of 121758-19-8

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General Information

CAS No. 121758-19-8
Cat. No. CS-0093700
Purity ≥98%
MDL No. MFCD00269673
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₈H₂₈N₂O₄S₂
Molecular Weight 520.66
Synonym(s) 4-methyl-N-[(1R,2R)-2-[(4-methylphenyl)sulfonylamino]-1,2-diphenylethyl]benzenesulfonamide
SMILES O=S(N[C@H](C1=CC=CC=C1)[C@H](NS(=O)(C2=CC=C(C)C=C2)=O)C3=CC=CC=C3)(C4=CC=C(C)C=C4)=O

Description

This chiral diamine features two p-toluenesulfonyl groups flanking a rigid ethylenediamine backbone, enabling high enantioselectivity in asymmetric catalysis. The bulky tosyl moieties provide steric shielding and enhance solubility in organic solvents. Designed for use in transition-metal-catalyzed reactions, this compound delivers predictable stereochemical outcomes with minimal racemization under standard conditions.

Application

(1R,2R)-N,N'-Di-p-tosyl-1,2-diphenyl-1,2-ethylenediamine serves as a chiral diamine ligand in asymmetric catalysis, enabling enantioselective transformations through well-defined coordination modes. Its rigid biphenyl backbone and bulky tosyl groups enhance stereocontrol and stability, facilitating efficient metal complexation with transition metals such as Cu(II) and Ni(II). The compound exhibits excellent bench stability, simplifies purification, and demonstrates broad functional group tolerance in standard asymmetric synthesis workflows.

Synthesis

Route1
- In-stock
  
  35132-20-8
- 98-59-9
- ~88%
- In-stock
  
  121758-19-8
References
- Stones, Graham; Tripoli, Regis; McDavid, Colin L.; Roux-Duplgtre, Kewin; Kennedy, Alan R.; Sherrington, David C.; Gibson, Colin L. Organic and Biomolecular Chemistry, 2008 , vol. 6, # 2 p. 374 - 384
Route2
- In-stock
  
  29841-69-8
- 98-59-9
- ~%
- In-stock
  
  121758-19-8
References
- Kucherenko, Alexander S.; Siyutkin, Dmitry E.; Nigmatov, Albert G.; Chizhov, Alexander O.; Zlotin, Sergei G. Advanced Synthesis and Catalysis, 2012 , vol. 354, # 16 p. 3078 - 3086

Safety Information

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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 92.34
LogP 5.04284
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 9

Key Words

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(1R,2R)-N,N'-Di-p-tosyl-1,2-diphenyl-1,2-ethylenediamine

CAS No. 121758-19-8

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