35132-20-8

Basic information

• Product Name: (1R,2R)-(+)-1,2-Diphenylethylenediamine
• Synonyms: (R,R)-(+)-1,2-DIPHENYLETHYLENEDIAMINE;1,2-ETHANEDIAMINE, 1,2-DIPHENYL-, (1R,2R)-;(1R,2R)-DIPHENYL-ETHANE-1,2-DIAMINE;(1R,2R)-(+)-1,2-DIAMINO-1,2-DIPHENYLETHANE;(1R,2R)-(+)-1,2-DIPHENYL-1,2-ETHANEDIAMINE;(1R,2R)-1,2-DIPHENYL-1,2-ETHANEDIAMINE;(1R,2R)-(+)-1,2-DIPHENYL-1,2-ETHYLENEDIAMINE;(1R,2R)-(-)-1,2-DIPHENYLETHYLENEDIAMINE
• CAS NO: 35132-20-8
• Molecular Formula: C14H16N2
• Molecular Weight: 212.29
• EINECS: -0
• Product Categories: chiral;Chiral reagent;CHIRAL COMPOUNDS;Amines (Chiral);Analytical Chemistry;Asymmetric Synthesis;Chiral Building Blocks;e.e. / Absolute Configuration Determination (NMR);Enantiomer Excess & Absolute Configuration Determination;Synthetic Organic Chemistry;Amines and Derivatives;CHIRAL CHEMICALS;Chiral Compound;organic amine;Aromatics;Chiral Reagents;Miscellaneous Reagents;Chiral Nitrogen;DPEN Series
• Mol File: 35132-20-8.mol

Chemical Properties

• Melting Point: 79-83 °C(lit.)
• Boiling Point: 342.14°C (rough estimate)
• Flash Point: 199.9 °C
• Appearance: White to light yellow/Crystalline Powder
• Density: 1.0799 (rough estimate)
• Vapor Pressure: 3.48E-05mmHg at 25°C
• Refractive Index: 103 ° (C=1, EtOH)
• Storage Temp.: 2-8°C
• PKA: 9.78±0.10(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 2369988
• CAS DataBase Reference: (1R,2R)-(+)-1,2-Diphenylethylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-(+)-1,2-Diphenylethylenediamine(35132-20-8)
• EPA Substance Registry System: (1R,2R)-(+)-1,2-Diphenylethylenediamine(35132-20-8)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-23
• HazardClass: 8
• Hazardous Substances Data: 35132-20-8(Hazardous Substances Data)

Usage

Uses

Used in Analytical Chemistry:
(1R,2R)-(+)-1,2-Diphenylethylenediamine is used as a chiral solvation agent for the determination of enantiomeric excess of chiral acids by NMR. Its application is crucial in the analysis and characterization of chiral compounds, which are essential in the pharmaceutical industry for the development of drugs with specific biological activities.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (1R,2R)-(+)-1,2-Diphenylethylenediamine is used as a catalyst in various asymmetric reactions. This application is vital for the synthesis of enantiomerically pure compounds, which are often required for the development of effective and safe drugs. The use of this compound in asymmetric catalysis can lead to improved yields and selectivity, ultimately contributing to the production of high-quality pharmaceutical products.
Used in Chemical Synthesis:
(1R,2R)-(+)-1,2-Diphenylethylenediamine is also employed in chemical synthesis as a chiral auxiliary, aiding in the creation of complex molecular structures with specific stereochemistry. This is particularly important in the development of new materials and compounds with tailored properties for various applications, such as in the fields of materials science, agrochemicals, and specialty chemicals.

InChI:InChI=1/C14H16N2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-14H,15-16H2/p+2/t13-,14-/m1/s1

Upstream product

• 5969-70-0 9,10-dihydro-9,10-[o]benzenoanthracene-1,4-diol 
• 3519-82-2 9,10-diydro-9,10-[o]benzenoanthracene-1,4-dione 
• 106-51-4 p-benzoquinone 
• 951-87-1 rac-1,2-diphenylethylene-1,2-diamine 
• 5700-60-7 1,2-Diphenylethylenediamine 
• 132486-60-3 (-)-(1R,2R)-1,2-diphenylethane-1,2-diazide 
• 169532-36-9 (3S,5R,6R,8S)-3,8-Diisopropyl-5,6-diphenyl-1,10-dioxa-4,7-diaza-cyclotridecane-2,9-dione 
• 169532-35-8 (6S,8R,9R,11S)-6,11-Diisopropyl-8,9-diphenyl-1,4-dioxa-7,10-diaza-cyclododecane-5,12-dione 
• 144406-67-7 (3S,5R,6R,8S)-3,8-Diisopropyl-5,6-diphenyl-1,10-dioxa-4,7-diaza-cyclotetradecane-2,9-dione 
• 134731-67-2 (R,R)-trans-4,5-diphenylimidazolidin-2-one 
• 23873-81-6 benzildioxime 
• 218933-95-0 (1R,2R)-N,N'-Bis-((S)-2-methoxymethyl-pyrrolidin-1-yl)-1,2-diphenyl-ethane-1,2-diamine 
• 635298-66-7 (1R,4R,4'R,5'R)-4',5'-diphenylspiro[7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2,2'-imidazolidine] 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 

Downstream Products

• 31819-61-1 cis-5,6-diphenyl-piperazin-2-one 
• 1244-95-7 N,N'-Bis-<2-methyl-butyliden-(3)>-meso-1,2-diamino-1,2-diphenyl-ethan 
• 3190-15-6 N.N'-Bis-<1-propyl-aethyliden>-meso-1.2-diphenyl-aethylendiamin 
• 3190-05-4 N.N'-Bis-<2-dimethyl-propyliden>-meso-1.2-diphenyl-aethylendiamin 
• 1169-86-4 N,N'-Bis--meso-1,2-diamino-1,2-diphenyl-ethan 
• 3190-20-3 N.N'-Bis-<β.β'-diphenyl-isopropyliden>-meso-1.2-diphenyl-aethylendiamin 
• 853918-33-9 4,5-dihydro-4,5-diphenyl-2-(2-pyridyl)-imidazole 
• 951-87-1 rac-1,2-diphenylethylene-1,2-diamine 
• 3190-01-0 racem-N,N'-dibenzylidene-bibenzyl-α,α'-diyldiamine 
• 3190-01-0 N,N'-dibenzylidene-1,2-diphenylethane-1,2-diamine 
• 64994-18-9 4,7-dimethyl-5r,6c-diphenyl-[1,4,7]oxadiazonane 
• 1194395-27-1 [N,N'-bis-(2'-hydroxyphenyl)phenylmethylidene]-(R,S)-1,2-diamino-1,2-diphenylethane 

Relevant articles and documents

Substrate-directed stereoselectivity in vicinal diamine-catalyzed synthesis of warfarin

A new mechanism involving a diimine intermediate is proposed for vicinal diamine-catalyzed synthesis of warfarin. Decreasing the NCCN dihedral angle by varying the diamine results in an increase in the enantioselectivity of warfarin synthesis.

Cobalt-Catalyzed Radical Hydroamination of Alkenes with N-Fluorobenzenesulfonimides

An efficient and general radical hydroamination of alkenes using Co(salen) as catalyst, N-fluorobenzenesulfonimide (NFSI) and its analogues as both nitrogen source and oxidant was successfully disclosed. A variety of alkenes, including aliphatic alkenes, styrenes, α, β-unsaturated esters, amides, acids, as well as enones, were all compatible to provide desired amination products. Mechanistic experiments suggest that the reaction underwent a metal-hydride-mediated hydrogen atom transfer (HAT) with alkene, followed by a pivotal catalyst controlled SN2-like pathway between in situ generated organocobalt(IV) species and nitrogen-based nucleophiles. Moreover, by virtue of modified chiral cobalt(II)-salen catalyst, an unprecedented asymmetric version was also achieved with good to excellent level of enantiocontrol. This novel asymmetric radical C?N bond construction opens a new door for the challenging asymmetric radical hydrofunctionalization.

Diboron glycol ester as well as preparation method, intermediate and application thereof

The invention discloses diboron glycol ester as well as a preparation method, an intermediate and application thereof. The diboron glycol ester can be used for inducing reductive coupling reaction with imine as a substrate, and the substrate can be obtained by reaction of aldehyde and ammonia and is very easy to obtain and quite low in cost. The product can be separated from a reaction system onlyby acid-base operation without column chromatography purification, and the post-treatment mode is convenient and easy to operate. The yield of the obtained product is high, and protective group operation is not needed. The diboron glycol ester has chirality, the stereoselectivity of the reductive coupling reaction is generally excellent, and 99% ee chiral diamine can be obtained only through simple recrystallization. The diboron glycol ester can be obtained by reacting diol with diboron glycol ester, the diol is convenient to prepare and easy to amplify, the diol can be recycled from a reaction solution through simple acid-base operation, the recovery rate reaches 95%, and the preparation cost is further saved.

Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron

We herein report a general, practical, and highly efficient method for asymmetric synthesis of a wide range of chiral vicinal diamines via reductive coupling of imines templated by chiral diboron. The protocol features high enantioselectivity and stereospecificity, mild reaction conditions, simple operating procedures, use of readily available starting materials, and a broad substrate scope. The method signifies the generality of diboron-enabled [3,3]-sigmatropic rearrangement.

A New, Short, and Stereocontrolled Synthesis of C2-Symmetric 1,2-Diamines

The previously unknown 5-spirocyclohexylisoimidazole has been made efficiently and simply by reaction of ammonia, glyoxal hydrate, and cyclohexanone. It is a very useful precursor for the diastereocontrolled synthesis of many C2-symmetric 1,2-diamines, a class which is important for the generation of a variety of C2-symmetric reagents and catalysts for enantioselective synthesis.

Enantio- and Diastereoselective Nitro-Mannich Reaction of α-Aryl Nitromethanes with Amidosulfones Catalyzed by Phase-Transfer Catalysts

A high-yield, highly diastereo- and enantioselective nitro-Mannich reaction of α-aryl nitromethanes with amidosulfones catalyzed by a novel chiral phase-transfer catalyst, bearing multiple H-bonding donors, derived from quinine was developed. A variety of α-aryl nitromethanes and amidosulfones were investigated; and the corresponding products were obtained in excellent yields with excellent diastereo- and enantioselectivities (up to 99% yield, > 99:1 dr and >99% ee). As a demonstration of synthetic utility, the resulting β-nitroamines could be converted to corresponding meso-symmetric and optically pure unsymmetric anti-1,2-diarylethylenediamines.

Synergistic copper-TEMPO catalysis of intermolecular vicinal diamination of styrenes

A copper-catalyzed, 2,2,6,6-tetramethyl piperidine N-oxy radical-assisted intermolecular diamination of styrenes with N-fluorobenzenesulfonimide has been developed. The current protocol proved amenable to a diverse array of styrenes via cascade radical addition to readily afford synthetically useful aromatic vicinal diamines with exclusive diastereoselectivity.

Triptycene-Based Chiral and meso-N-Heterocyclic Carbene Ligands and Metal Complexes

Based on 1-amino-4-hydroxy-triptycene, new saturated and unsaturated triptycene-NHC (N-heterocyclic carbene) ligands were synthesized from glyoxal-derived diimines. The respective carbenes were converted into metal complexes [(NHC)MX] (M=Cu, Ag, Au; X=Cl, Br) and [(NHC)MCl(cod)] (M=Rh, Ir; cod=1,5-cyclooctadiene) in good yields. The new azolium salts and metal complexes suffer from limited solubility in common organic solvents. Consequently, the introduction of solubilizing groups (such as 2-ethylhexyl or 1-hexyl by O-alkylation) is essential to render the complexes soluble. The triptycene unit infers special steric properties onto the metal complexes that enable the steric shielding of selected areas close to the metal center. Next, chiral and meso-triptycene based N-heterocyclic carbene ligands were prepared. The key step in the synthesis of the chiral ligand is the Buchwald–Hartwig amination of 1-bromo-4-butoxy-triptycene with (1S,2S)-1,2-diphenyl-1,2-diaminoethane, followed by cyclization to the azolinium salt with HC(OEt)3. The analogous reaction with meso-1,2-diphenyl-1,2-diaminoethane provides the respective meso-azolinium salt. Both the chiral and meso-azolinium salts were converted into metal complexes including [(NHC)AuCl], [(NHC)RhCl(cod)], [(NHC)IrCl(cod)], and [(NHC)PdCl(allyl)]. An in situ prepared chiral copper complex was tested in the enantioselective borylation of α,β-unsaturated esters and found to give an excellent enantiomeric ratio (er close to 90:10).

Direct catalytic asymmetric mannich-type reaction of benzyl isocyanide: Stereoselective synthesis of 1,2-diarylethylenediamines

A direct catalytic asymmetric Mannich-type reaction of benzyl isocyanide using a CuI catalyst and N-(diphenylthiophosphinoyl)imines was developed. The simultaneous activation strategy by soft-soft interaction was the key to promote the reaction using a weakly acidic pronucleophile, benzyl isocyanide. The spontaneous cyclization of the Mannich adduct afforded the corresponding enantioenriched imidazolines, which could be precursors for a variety of 1,2-diarylethylenediamines. Enantioenriched 4,5-diarylimidazolines were directly accessed by catalytic asymmetric C-C bond-forming reaction of benzyl isocyanide and N-(thiophosphinoyl)aldimines. The imidazolines were readily transformed into enantioenriched 1,2-diarylethylenediamines.

Lipase-catalyzed desymmetrization of meso-1,2-diaryl-1,2-diaminoethanes

The synthesis and enzyme-catalyzed desymmetrization of meso-1,2-diaryl-1,2- diaminoethanes have been investigated. A family of aromatic meso-1,2-diamines, containing different substitution patterns in the aromatic ring, was first prepared and then desymmetrized enantioselectively using lipases as biocatalysts. Selective alkoxycarbonylation of one of the amino groups was achieved using allyl carbonates, isolating the corresponding allyl monocarbamates with moderate to high enantiomeric excess at 45 C. Candida antarctica lipase types A (CAL-A) and B (CAL-B) displayed the best activities and stereopreferences, with a dramatic influence being observed depending on the diamine structure. Non substituted and para-substituted aryldiamines led to the formation of allyl carbamates with good enantiomeric excess, using CAL-A for the less hindered substrates and CAL-B for the more hindered ones. On the other hand meta- and ortho-derivatives afforded low or negligible conversions and selectivities, respectively.