156730-49-3

Basic information

• Product Name: 1S,2S-bis[(1R)-1-phenylethyl]-1,2-diphenyl-1,2-EthanediaMine
• Synonyms: 1S,2S-bis[(1R)-1-phenylethyl]-1,2-diphenyl-1,2-EthanediaMine
• CAS NO: 156730-49-3
• Molecular Formula: C₃₀H₃₂N₂
• Molecular Weight: 420.58848
• Mol File: 156730-49-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1S,2S-bis[(1R)-1-phenylethyl]-1,2-diphenyl-1,2-EthanediaMine(CAS DataBase Reference)
• NIST Chemistry Reference: 1S,2S-bis[(1R)-1-phenylethyl]-1,2-diphenyl-1,2-EthanediaMine(156730-49-3)
• EPA Substance Registry System: 1S,2S-bis[(1R)-1-phenylethyl]-1,2-diphenyl-1,2-EthanediaMine(156730-49-3)

Safety Data

• Hazardous Substances Data: 156730-49-3(Hazardous Substances Data)

Usage

Explanation

The compound consists of 26 carbon atoms, 29 hydrogen atoms, and 3 nitrogen atoms.

Explanation

The complex structure includes two benzene rings (six-membered carbon rings) with a phenylethyl group (a phenyl group attached to an ethyl chain) on each ring, linked by a central ethane (two-carbon) backbone.

Explanation

The compound has two non-superimposable mirror image forms, which means it can exist as two different isomers with the same molecular formula but different spatial arrangements.

Explanation

As a chiral molecule, 1S,2S-bis[(1R)-1-phenylethyl]-1,2-diphenyl-1,2-ethanediamine can be used as a chiral ligand in asymmetric synthesis reactions, helping to create chiral products with high selectivity.

Explanation

The compound is often used in metal-catalyzed asymmetric hydrogenation processes, which involve the addition of hydrogen to a molecule in a chiral-selective manner, resulting in the formation of chiral products.

Explanation

Researchers have studied 1S,2S-bis[(1R)-1-phenylethyl]-1,2-diphenyl-1,2-ethanediamine for its potential use in organic electronic materials, such as in the development of organic solar cells or organic light-emitting diodes (OLEDs).

Explanation

The compound can be used as a chiral selector in chromatography, a technique for separating and analyzing mixtures of compounds. As a chiral selector, it can help to separate and analyze chiral compounds based on their different interactions with the chiral selector.

Molecular structure

Two benzene rings with phenylethyl groups attached, connected by an ethane backbone

Chiral molecule

存在两种非超posable的镜像异构体

Chiral ligand

Used in asymmetric synthesis reactions

Metal-catalyzed asymmetric hydrogenation

Involved in hydrogenation processes

Organic electronic materials

Potential applications in the field

Chiral selector in chromatography

Used for separating chiral compounds

Upstream product

• 100-59-4 phenylmagnesium chloride 
• 90580-93-1 N,N'-bis<(R)-1-phenylethyl>-1,2-ethanediimine 
• 56941-77-6 (R)-1-phenylethyl(benzylidene)amine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 129171-89-7 1,4-bis<(R)-α-methylbenzyl>-1,4-diaza-1,3-butadiene 

Downstream Products

• 891271-42-4 (+)-(4S,5S)-2-(2-pyridinyl)-4,5-diphenyl-1,3-bis((R)-1-phenylethyl)imidazolidine 
• 891271-43-5 (-)-(4S,5S)-2-(2-chlorophenyl)-4,5-diphenyl-1,3-bis((R)-1-phenylethyl)imidazolidine 

Relevant articles and documents

Simple Synthesis of a C2 Symmetric Vicinal Diamine: Highly Diastereoselective Grignard Addition toa Chiral Bis-Imine

The reaction of the enantiomerically pure bis-imine derived from glyoxal and (R)-α-methylbenzylamine with PhMgCl in diethylether is highly diastereoselective , resulting in the selective formation of the C2 symmetric vicinal diamine 7.

Diastereoselective synthesis of 1,2-diphenyl-1,2-diaminoethanes by Yb(OTf)3 accelerated reductive coupling of imines

New reaction protocols have been established to perform the reductive coupling of N-benzyl benzaldimines to 1,2-diphenyl-1,2-diaminoethanes in mild, stereoselective, and catalytic conditions by the use of SmI2 and Yb(OTf)3.

Design, development, and scale-up of a selective meso-epoxide desymmetrization process

A pilot-plant scale desymmetrization of the cyclic meso-epoxide 4b, using a chiral lithium amide prepared from symmetrical diamine 17, was designed and implemented to provide allylic alcohol 3b in high yield and greater than 99% ee. This chiral alcohol was converted to ketone 2b, a key intermediate in a new asymmetric synthesis of LY459477. Chiral diamine 17 was prepared from a readily available chiral precursor, (R)-α-methylbenzylamine, and could be recovered from the reaction mixture and reused. Studies performed to probe the mechanism of the rearrangement reaction of epoxide 4b showed that diamine 17 provided an optimal combination of selectivity and scaleability for this process.