221226-19-3

Basic information

• Product Name: 1R,2R-N,N'-bis(phenylMethyl)-1,2-diphenyl-1,2-EthanediaMine
• Synonyms: 1R,2R-N,N'-bis(phenylMethyl)-1,2-diphenyl-1,2-EthanediaMine;(1R,2R)-1,2-Diphenyl-N1,N2-bis(phenylmethyl)-1,2-ethanediamine;(1R,2R)-1,2-Diphenyl-N1,N2-bis(phenylmethyl)-1,2-ethan ediamine,99%e.e.;(1R,2R)-N,N'-Bis(phenylmethyl)-1,2-diphenyl-1,2-ethaned iamine,99%e.e.
• CAS NO: 221226-19-3
• Molecular Formula: C₂₈H₂₈N₂
• Molecular Weight: 392.53532
• Mol File: 221226-19-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 1R,2R-N,N'-bis(phenylMethyl)-1,2-diphenyl-1,2-EthanediaMine(CAS DataBase Reference)
• NIST Chemistry Reference: 1R,2R-N,N'-bis(phenylMethyl)-1,2-diphenyl-1,2-EthanediaMine(221226-19-3)
• EPA Substance Registry System: 1R,2R-N,N'-bis(phenylMethyl)-1,2-diphenyl-1,2-EthanediaMine(221226-19-3)

Safety Data

• Hazardous Substances Data: 221226-19-3(Hazardous Substances Data)

Usage

Chiral diamine compound

The compound has a chiral center, which means it can exist in two different forms (enantiomers) that are non-superimposable mirror images of each other.

Use as a ligand

1R,2R-N,N'-bis(phenylMethyl)-1,2-diphenyl-1,2-EthanediaMine is commonly used to bind to metal ions in asymmetric catalysis and organic synthesis.

Efficient catalysis

This compound is known for its ability to efficiently catalyze various chemical reactions, such as asymmetric hydrogenation and cross-coupling reactions.

Formation of chiral products

The catalyzed reactions lead to the formation of chiral products with high enantioselectivity, which is crucial for the development of pharmaceuticals and other fine chemicals.

Unique structure

The specific arrangement of phenyl and methyl groups in the compound contributes to its unique structure and properties.

Valuable tool in pharmaceutical development

Due to its ability to produce chiral products with high enantioselectivity, this compound is a valuable tool in the development of new pharmaceuticals and other fine chemicals.

Potential applications in material science and nanotechnology

The compound's unique properties have also attracted interest in the fields of material science and nanotechnology for potential applications in these areas.

Upstream product

• 35132-20-8 (R,R)-1,2-diphenylethylenediamine 
• 100-44-7 benzyl chloride 
• 780-25-6 N-benzylidene benzylamine 
• 484001-72-1 (4R,5R)-2,2-dimethyl-4,5-diphenylimidazolidine 

Downstream Products

• 138421-29-1 (4R,5R)-1,3-Dibenzyl-2-chloro-4,5-diphenyl-[1,3,2]diazaphospholidine 
• 138421-34-8 (4R,5R)-1,3-Dibenzyl-4,5-diphenyl-[1,3,2]diazaphospholidine 2-oxide 
• 138421-41-7 (4R,5R)-1,2,3-Tribenzyl-4,5-diphenyl-[1,3,2]diazaphospholidine 2-oxide 

Relevant articles and documents

Stereo- and Regioselectivity of Reactions of Siliranes with Aldehydes and Related Substrates

Siliranes undergo stereoselective and regioselective insertions of benzaldehyde to provide oxasilacyclopentane products. The thermal reaction (>100°C) leads to more decomposition and side products, whereas the catalyzed variant (t-BuOK, 95%). Treatment of siliranes with enolizable aldehydes leads to silyl enol ethers. The reaction of a silirane at high temperatures with an imine leads to reductive dimerization, presumably by way of intermediate-free silylene. The mechanism for the catalyzed insertion of benzaldehyde is discussed.

Nitroalkenes in the Ni(II) Catalyzed Asymmetric Michael Addition. Convenient Route to the Key Intermediate of Brivaracetam

A series of Ni(II) complexes with novel chiral ligands derived from (1R,2R)-1,2-diphenylethane-1,2-diamine was synthesized. The catalytic activity of these complexes in the asymmetric Michael reaction is demonstrated. Asymmetric addition of diethyl malonate to ω-nitrostyrene and 1-nitropent-1-ene in the presence of these complexes leads to the enantiomerically enriched diethyl (S)-2-(2-nitro-1-phenylethyl)malonate (up to 96 % ee) and (R)-diethyl 2-(1-nitropenthan-2-yl)malonate (up to 91 % ee). (4R)-4-Propylpyrrolidin-2-one, the key intermediate of antiepileptic drug brivaracetam, was obtained from the corresponding nitroester.

Zinc Acetate-Catalyzed Enantioselective Hydrosilylation of Ketones

Zinc acetate complexes with a chiral diphenylethylenediamine (DPEDA)-derived ligand have been proved to be efficient catalysts for the enantioselective hydrosilylation of aryl ketones. Replacing pyrophoric dialkylzinc with the readily available zinc salt simplifies the procedures and provides excellent conversions (up to >99%) and enantioselectivities (ees up to 97%).