70749-06-3

Basic information

• Product Name: (1S,2S)-(-)-N,N'-DIMETHYL-1,2-DIPHENYL-1,2-ETHANE DIAMINE
• Synonyms: (1S,2S)-(-)-N,N'-DIMETHYL-1,2-DIPHENYL-1,2-ETHANE DIAMINE;(1S,2S)-(-)-N,N'-DIMETHYL-1,2-DIPHENYLETHYLENEDIAMINE;(1S,2S)-(-)-N,N'-Dimethyl-1,2-diphenyl-1,2-ethane diamine,99%;(1S,2S)-N,N'-Dimethyl-1,2-diphenyl-1,2-ethylenediamine;(1S,2S)-N1,N2-dimethyl-1,2-diphenylethane-1,2-diamine
• CAS NO: 70749-06-3
• Molecular Formula: C₁₆H₂₀N₂
• Molecular Weight: 240.34
• Product Categories: Chiral Compound
• Mol File: 70749-06-3.mol
• Article Data: 17

Chemical Properties

• Melting Point: 48-51 °C
• Boiling Point: 373.06°C (rough estimate)
• Flash Point: 110℃
• Appearance: White to light yellow/Crystals or Crystalline Powder
• Density: 1.0485 (rough estimate)
• Refractive Index: 1.5519 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 9.14±0.30(Predicted)
• CAS DataBase Reference: (1S,2S)-(-)-N,N'-DIMETHYL-1,2-DIPHENYL-1,2-ETHANE DIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-(-)-N,N'-DIMETHYL-1,2-DIPHENYL-1,2-ETHANE DIAMINE(70749-06-3)
• EPA Substance Registry System: (1S,2S)-(-)-N,N'-DIMETHYL-1,2-DIPHENYL-1,2-ETHANE DIAMINE(70749-06-3)

Safety Data

• Hazard Codes: C,N,Xn
• Statements: 34-50-22
• Safety Statements: 45-36/37/39-26-61
• Hazardous Substances Data: 70749-06-3(Hazardous Substances Data)

Usage

Uses

(1S,2S)-N,N′-Dimethyl-1,2-diphenyl-1,2-ethylenediamine can be used as:A precursor for the synthesis of chiral imidazolinium salts, which are used as catalysts for aza Diels?Alder reaction and as shift reagents for potassium salt of Mosher′s acid.A ligand in the preparation of 2,3-dihydrobenzofurans and indanes by reacting alkyl halides with alkyl electrophiles using nickel/diamine catalyst.A ligand in the synthesis of carbamates, sulfonamides, and sulfones through alkyl-alkyl Suzuki reaction using Ni catalyst.

Upstream product

• 622-29-7 N-Benzylidenemethylamine 
• 69019-77-8 N,N'-Dimethyl-1,2-diphenyl-N,N'-bis-trimethylsilanyl-ethane-1,2-diamine 
• 100-52-7 benzaldehyde 
• 3969-04-8 Diethyl N,N'-(1,2-diphenylethylene)biscarbamate 
• 29841-69-8 (S,S)-1,2-diphenyl-1,2-diaminoethane 
• 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 
• 951-87-1 rac-1,2-diphenylethylene-1,2-diamine 
• 60509-62-8 (R,S)-N,N'-dimethyl-1,2-diphenylethylenediamine 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 119092-13-6 (4S,5S)-1,3-Dimethyl-2-(2-methyl-pentyl)-4,5-diphenyl-imidazolidine 
• 138311-92-9 (4S,5S)-2-((Z)-2-Iodo-vinyl)-1,3-dimethyl-4,5-diphenyl-imidazolidine 
• 22751-68-4 (S,S)-N,N'-dimethyl-1,2-diphenylethane-1,2-diamine 
• 118628-68-5 (1R,2R)-(+)-N,N'-dimethyl-1,2-diphenyl-ethylenediamine 
• 198625-67-1 (4S,5S)-2-chloro-1,3-dimethyl-4,5-diphenylimidazolinium chloride 
• 64994-19-0 1,3-dimethyl-r-2,c-4,t-5-triphenylimidazolidine 
• 704890-52-8 2-chloro-1,3-dimethyl-4,5-diphenyl-1,3,2-diazaphospholidine 
• 119092-10-3 3-[3-((4S,5S)-1,3-Dimethyl-4,5-diphenyl-imidazolidin-2-yl)-oxiranyl]-propionic acid methyl ester 
• 128860-91-3 (E)-(R)-1-((4S,5S)-1,3-Dimethyl-4,5-diphenyl-imidazolidin-2-yl)-oct-1-en-3-ol 
• 128946-66-7 (E)-(S)-1-((4S,5S)-1,3-Dimethyl-4,5-diphenyl-imidazolidin-2-yl)-oct-1-en-3-ol 
• 133643-21-7 (4S,5S)-2--1,3-dimethyl-4,5-diphenylimidazolidine 
• 119092-11-4 (4S,5S)-1,3-Dimethyl-4,5-diphenyl-2-(2-phenyl-propyl)-imidazolidine 
• 135075-64-8 Methyl (4S,5S)-(-)-(E)-3-(1,3-Dimethyl-4,5-diphenylimidazolidin-2-yl)propenoate 
• 135075-64-8 Methyl (4RS,5RS)-(E)-3-(1,3-Dimethyl-4,5-diphenylimidazolidin-2-yl)propenoate 

Relevant articles and documents

Development of Chiral Organosuperbase Catalysts Consisting of Two Different Organobase Functionalities

In the field of chiral Br?nsted base catalysis, a new generation of chiral catalysts has been highly anticipated to overcome the intrinsic limitation of pronucleophiles that are applicable to the enantioselective reactions. Herein, we reveal conceptually new chiral Br?nsted base catalysts consisting of two different organobase functionalities, one of which functions as an organosuperbase and the other as the substrate recognition site. Their prominent activity, which stems from the distinctive cooperative function by the two organobases in a single catalyst molecule, was demonstrated in the unprecedented enantioselective direct Mannich-type reaction of α-phenylthioacetate as a less acidic pronucleophile. The present achievement would provide a new guiding principle for the design and development of chiral Br?nsted base catalysts and significantly broaden the utility of Br?nsted base catalysis in asymmetric organic synthesis.

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.