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
• Article Data: 44

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

Description

(1R,2R)-(+)-1,2-Diphenylethylenediamine is a white to light yellow crystal powder that serves as a crucial chiral solvation agent in the determination of enantiomeric excess of chiral acids by Nuclear Magnetic Resonance (NMR) spectroscopy. It is also utilized in various catalyst systems for asymmetric reactions, playing a significant role in the synthesis of enantiomerically pure compounds.

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

• 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 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 2325-10-2 (S,S)-hydrobenzoin 
• 132486-59-0 (+)-(1S,2S)-1,2-diphenyl-1,2-ditosyloxyethane 
• 1073145-36-4 C₁₄H₁₆N₂*C₄H₆O₆ 
• 5396-98-5 2,3-diphenyl-1,4-diazaspiro[4.5]deca-1,3-diene 

Downstream Products

• 31819-61-1 cis-5,6-diphenyl-piperazin-2-one 
• 142819-75-8 meso-N,N'-diacetyl-1,2-diamino-1,2-diphenylethane 
• 642-04-6 2,3,5,6-tetraphenylpyrazine 
• 3408-55-7 N.N'-Bis-<2.4.6-trimethyl-benzyliden>-meso-1.2-diphenyl-aethylendiamin 
• 1176-92-7 N_.N'-Bis-dipropylmethylen-meso-1.2-diphenyl-aethylendiamin 
• 1261-93-4 N_.N'-Bis-diisopentylmethylen-meso-1.2-diphenyl-aethylendiamin 
• 41013-40-5 (C₆H₆(CH₃)(C(CH₃)2)(O)(CHNCHC₆H₅))2 
• 3239-07-4 N_.N'-Bis-cyclohexyliden-meso-1.2-diphenyl-aethylendiamin 
• 3190-01-0 meso-α.α'-bis-benzylidenamino-bibenzyl 
• 41013-29-0 N,N'-disalicylidene-(R,S)(S,R)-1,2-diphenyl-1,2-ethanediamine 
• 228704-38-9 (1R,2R)-N,N′-bis-(salicylidene)-1,2-diphenyl-1,2-ethanediamine 
• 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 
• 64994-17-8 cis-5,6-diphenyl-[1,4,7]oxadiazonane 

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.

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.

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.