60508-97-6

Basic information

• Product Name: (1R,2R)-N,N'-Dimethyl-1,2-diphenyl-1,2-ethylenediamine
• Synonyms: (1R,2R)-N,N'-Dimethyl-1,2-diphenyl-1,2-ethylenediamine;(1S,2S)-N,N'-Dimethyl-1,2-diphenyl-1,2-ethylenediamine 97%
• CAS NO: 60508-97-6
• Molecular Formula: C₁₆H₂₀N₂
• Molecular Weight: 240
• Mol File: 60508-97-6.mol
• Article Data: 17

Chemical Properties

• Melting Point: 48-53°C
• Boiling Point: 346.4±37.0 °C(Predicted)
• Flash Point: >110℃
• Appearance: /
• Density: 1.022
• PKA: 9.14±0.30(Predicted)
• CAS DataBase Reference: (1R,2R)-N,N'-Dimethyl-1,2-diphenyl-1,2-ethylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-N,N'-Dimethyl-1,2-diphenyl-1,2-ethylenediamine(60508-97-6)
• EPA Substance Registry System: (1R,2R)-N,N'-Dimethyl-1,2-diphenyl-1,2-ethylenediamine(60508-97-6)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 60508-97-6(Hazardous Substances Data)

Usage

General Description

"(1R,2R)-N,N'-Dimethyl-1,2-diphenyl-1,2-ethylenediamine" is a chemical compound that belongs to the class of diamines. It is a chiral compound with two stereocenters, and the (1R,2R) configuration indicates the relative orientation of the substituents around these stereocenters. (1R,2R)-N,N'-Dimethyl-1,2-diphenyl-1,2-ethylenediamine is commonly used as a chiral auxiliary in asymmetric synthesis and is also used as a ligand in coordination chemistry. It has applications in the pharmaceutical industry, particularly in the development of chiral drugs and catalysts. Additionally, it has been studied for its potential antiviral and antitumor properties.

Upstream product

• 622-29-7 N-Benzylidenemethylamine 
• 29841-69-8 (S,S)-1,2-diphenyl-1,2-diaminoethane 
• 69019-77-8 N,N'-Dimethyl-1,2-diphenyl-N,N'-bis-trimethylsilanyl-ethane-1,2-diamine 
• 100-52-7 benzaldehyde 
• 60509-62-8 (R,S)-N,N'-dimethyl-1,2-diphenylethylenediamine 
• 3969-04-8 Diethyl N,N'-(1,2-diphenylethylene)biscarbamate 
• 22751-68-4 (+/-)-N,N'-dimethyl-1,2-diphenyl-1,2-ethylenediamine 
• 220665-71-4 N-((1S,2S)-2-Formylamino-1,2-diphenyl-ethyl)-formamide 
• 234753-20-9 diethyl ((1S,2S)-1,2-diphenylethane-1,2-diyl)dicarbamate 
• 541-41-3 chloroformic acid ethyl ester 
• 951-87-1 rac-1,2-diphenylethylene-1,2-diamine 

Downstream Products

• 119092-13-6 (4S,5S)-1,3-Dimethyl-2-(2-methyl-pentyl)-4,5-diphenyl-imidazolidine 
• 135075-64-8 Methyl (4RS,5RS)-(E)-3-(1,3-Dimethyl-4,5-diphenylimidazolidin-2-yl)propenoate 
• 135075-64-8 Methyl (4S,5S)-(-)-(E)-3-(1,3-Dimethyl-4,5-diphenylimidazolidin-2-yl)propenoate 
• 138311-92-9 (4S,5S)-2-((Z)-2-Iodo-vinyl)-1,3-dimethyl-4,5-diphenyl-imidazolidine 
• 119092-11-4 (4S,5S)-1,3-Dimethyl-4,5-diphenyl-2-(2-phenyl-propyl)-imidazolidine 
• 64994-19-0 1,3-dimethyl-r-2,c-4,t-5-triphenylimidazolidine 
• 119092-08-9 (4S,5S)-2-Cyclohex-3-enyl-1,3-dimethyl-4,5-diphenyl-imidazolidine 
• 438207-07-9 (3S,4S)-2,5-dimethyl-1-(2-trimethylsiloxyphenyl)-2,5-diaza-4-phospholidine 
• 171560-05-7 (4S,5S)-2-<(S)-1-aminoethyl>-1,3-dimethyl-4,5-diphenylimidazolidine 

Relevant articles and documents

Substrate-Induced Dimerization Assembly of Chiral Macrocycle Catalysts toward Cooperative Asymmetric Catalysis

An artificial system of substrate-induced dimerization assembly of chiral macrocycle catalysts enables a highly cooperative hydrogen-bonding activation network for efficient enantioselective transformation. These macrocycles contain two thiourea and two chiral diamine moieties and dimerize with sulfate to form a sandwich-like assembly. The macrocycles then adopt an extended conformation and reciprocally complement the hydrogen-bonding interaction sites. Inspired by the guest-induced dynamic assembly, these macrocycles catalyze the decarboxylative Mannich reaction of cyclic aldimines containing a sulfamate heading group. The imine substrate can be activated toward nucleophilic attack of β-ketoacid by a cooperative hydrogen-bonding network enabled by sulfamate-induced dimerization assembly of the macrocycle catalysts. Highly efficient (>95 % yield in most cases) and enantioselective (up to 97.5:2.5 er) transformation of a variety of substrates using only 5 mol % macrocycle was achieved.

Dynamic Kinetic Resolution of Heterobiaryl Ketones by Zinc-Catalyzed Asymmetric Hydrosilylation

A diastereo- and highly enantioselective dynamic kinetic resolution (DKR) of configurationally labile heterobiaryl ketones is described. The DKR proceeds by zinc-catalyzed hydrosilylation of the carbonyl group, thus leading to secondary alcohols bearing axial and central chirality. The strategy relies on the labilization of the stereogenic axis that takes place thanks to a Lewis acid–base interaction between a nitrogen atom in the heterocycle and the ketone carbonyl group. The synthetic utility of the methodology is demonstrated through stereospecific transformations into either N,N-ligands or appealing axially chiral, bifunctional thiourea organocatalysts.

Synthesis, resolution, and application of 2,2′-bis(diphenylphosphino) -3,3′-binaphtho[b]furan (BINAPFu)

(±)-2,2′-Bis(diphenylphosphino)-3,3′-binaphtho[2,1-b] furan (BINAPFu) was synthesized from 2-naphthoxyacetic acid in a five-step sequence in 62% overall yield. A variety of reported resolution procedures for biaryl bisphosphines did not work with (±)-BINAPFu; thus, a new resolution method was developed, involving the Staudinger reaction of the aforementioned racemate of BINAPFu with an enantiopure camphor sulfonyl azide derivative. The resulting diastereomeric phosphinimines were separated by flash chromatography. Subsequent hydrolysis to the corresponding bis-phosphine oxide and trichlorosilane reduction provided enantiopure BINAPFu. The absolute stereochemical configuration of BINAPFu was established by X-ray crystallography. BINAPFu was compared with commercially available 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP) in Pd(0)-catalyzed intermolecular Heck reactions. Investigation of the Heck arylation of 2,3-dihydrofuran showed BINAPFu to be more efficacious than BINAP in dioxane at 30°C. A variety of phosphorus selenides were prepared, and the 1JP-Se coupling constants measured, to obtain a comparative scale of parent phosphine basicity. The phosphorus atoms in BINAPFu were found to be electron deficient when compared with BINAP but slightly more electron rich than trifurylphosphine.