951-87-1

Basic information

• Product Name: meso-1,2-Diphenylethylenediamine
• Synonyms: MESO-1,2-DIPHENYLETHYLENEDIAMINE;meso-1,2-Diphenylethylenediamine 98%;meso-1,2-Diphenylethylenediamine
• CAS NO: 951-87-1
• Molecular Formula: C₁₄H₁₆N₂
• Molecular Weight: 212.29
• Product Categories: Nitrogen Compounds;Organic Building Blocks;Polyamines
• Mol File: 951-87-1.mol

Chemical Properties

• Melting Point: 118-122°C
• Boiling Point: 353.9 °C at 760 mmHg
• Flash Point: 199.9 °C
• Appearance: /
• Density: 1.106 g/cm³
• Vapor Pressure: 3.48E-05mmHg at 25°C
• Refractive Index: 1.619
• PKA: 9.78±0.10(Predicted)
• CAS DataBase Reference: meso-1,2-Diphenylethylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: meso-1,2-Diphenylethylenediamine(951-87-1)
• EPA Substance Registry System: meso-1,2-Diphenylethylenediamine(951-87-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 951-87-1(Hazardous Substances Data)

Usage

Uses

Used in the Production of Polyurethane Materials:
Meso-1,2-Diphenylethylenediamine is used as a catalyst in the production of polyurethane foams, elastomers, and coatings. It facilitates the reaction process, enhancing the efficiency and quality of the final products.
Used in Polymer Industry:
In the polymer industry, meso-1,2-Diphenylethylenediamine serves as a stabilizer for certain types of polymers, helping to improve their durability and resistance to degradation.
Used in Pharmaceutical Synthesis:
Meso-1,2-Diphenylethylenediamine is utilized as an intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and medicinal compounds.
Used in Organic Compound Synthesis:
meso-1,2-Diphenylethylenediamine is also employed as an intermediate in the synthesis of other organic compounds, broadening its applications across different chemical industries.
Safety Considerations:
Given its potential health hazards, meso-1,2-Diphenylethylenediamine should be handled with care to avoid irritation to the skin, eyes, and respiratory system. Proper safety measures and personal protective equipment are essential when working with this compound.

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/t13-,14+

Upstream product

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Downstream Products

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• 81601-99-2 (R,S)-2,3-diphenylpiperazine 
• 951-87-1 rac-1,2-diphenylethylene-1,2-diamine 
• 3190-01-0 racem-N,N'-dibenzylidene-bibenzyl-α,α'-diyldiamine 
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Relevant articles and documents

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.

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.

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.

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.

Enantioseparation of 1-arylethanols via a supramolecular chiral host consisting of N-(2-naphthoyl)-l-aspartic acid and an achiral diamine

A supramolecular chiral host consisting of N-(2-naphthoyl)-l-aspartic acid (L-1) and meso-1,2-diphenylethylenediamine (2) is effective in enantioseparation of 1-arylethanols (up to 96% ee with 100% inclusion ratio). Here we report three different methods to prepare the inclusion crystals and discuss the chiral recognition mechanism on the basis of X-ray crystallography results.

A synthesis of the pseudopterosin A-F aglycone

The synthesis of the pseudopterosin A-F aglycone from 3-methylcatechol features (a) the use of asymmetric Ireland-Claisen and aryl Claisen rearrangements to install three of the four stereocentres present in the molecule and (b) an A→AB→ABC annulation strategy using ring-closing metathesis and cationic cyclisation reactions as the key steps.

Design, synthesis, and biological evaluation of imidazoline derivatives as p53-MDM2 binding inhibitors

Three series of novel imidazoline derivatives were designed, synthesized, and evaluated for their p53-MDM2 binding inhibitory activities, and anti-proliferation activities against PC3, A549, KB, and HCT116 cancer cell lines. Five of the tested compounds showed enhanced p53-MDM2 binding inhibitory potency and anti-proliferation activities in comparison with that of Nutlin-1. Flow cytometric analysis indicated that compound 7c, one of the most potent p53-MDM2 binding inhibitors with a Ki value of 0.6 μM, showed its ability to arrest cell cycle progression.

Reductive coupling of aromatic oxims and azines to 1,2-diamines using Zn-MsOH or Zn-TiCl4

The reduction of aromatic aldoxims and azines with Zn in the presence of MsOH or TiCl4 afforded N,N′-unsubstituted 1,2-diamines in one-step. The reductive coupling with Zn-MsOH gave meso 1,2-diamines selectively, whereas dl 1,2-diamines were fo

A simplified synthesis of (±)-1,2-Diphenyl-1,2-diaminoethane (1) from benzaldehyde and ammonia. Revision of the structures of the long-known intermediates 'hydrobenzamide' and 'amarine'

A new pathway for the simple, stereocontrolled and economical synthesis of (±)-1 from benzaldehyde is described. The structures of two intermediates (Scheme 1) have been revised to those shown in Scheme 2.