186769-18-6

Basic information

• Product Name: (1S,2S)-1,2-BIS(2,4,6-TRIMETHYLPHENYL)ETHYLENEDIAMINE
• Synonyms: (1S,2S)-1,2-BIS(2,4,6-TRIMETHYLPHENYL)ETHYLENEDIAMINE;(1S,2S)-1,2-DIMESITYLETHYLENEDIAMINE;(1S,2S)-1,2-DIAMINO-1,2-DIMESITYLETHANE;(1S,2S)-1,2-BIS(2,4,5-TRIMETHYLPHENYL)ETHYLENEDIAMINE EP;(S,S)-1,2-Bis(2,4,6-trimethylphenyl)-1,2-ethanediamine dihydrochloride;(1S,2S)-1,2-Bis(2,4,6-trimethylphenyl)-1,2-ethanediamine hydrate dihydrochloride;(1S,2S)-1,2-Bis(2,4,6-trimethylphenyl)ethylenediamine hydrate dihydrochloride;(1S,2S)-1,2-Diamino-1,2-dimesitylethane (1S,2S)-1,2-Dimesitylethylenediamine
• CAS NO: 186769-18-6
• Molecular Formula: C20H28N2
• Molecular Weight: 296.45
• Product Categories: Amines (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry
• Mol File: 186769-18-6.mol

Chemical Properties

• Melting Point: >300 °C
• Boiling Point: 451.7°C at 760 mmHg
• Flash Point: 272.3°C
• Appearance: /
• Density: 1.024g/cm³
• Vapor Pressure: 2.37E-08mmHg at 25°C
• Refractive Index: 1.579
• Solubility: slightly sol. in dichloromethane
• CAS DataBase Reference: (1S,2S)-1,2-BIS(2,4,6-TRIMETHYLPHENYL)ETHYLENEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-1,2-BIS(2,4,6-TRIMETHYLPHENYL)ETHYLENEDIAMINE(186769-18-6)
• EPA Substance Registry System: (1S,2S)-1,2-BIS(2,4,6-TRIMETHYLPHENYL)ETHYLENEDIAMINE(186769-18-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 186769-18-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
(1S,2S)-1,2-BIS(2,4,6-TRIMETHYLPHENYL)ETHYLENEDIAMINE is used as a catalyst in the pharmaceutical and agrochemical industries for its ability to facilitate various chemical reactions, contributing to the synthesis of complex organic molecules.
Used in Asymmetric Catalysis:
As a chiral diamine, (1S,2S)-1,2-BIS(2,4,6-TRIMETHYLPHENYL)ETHYLENEDIAMINE is used as a ligand in asymmetric catalysis, playing a crucial role in the selective formation of enantiomers, which is essential for the production of biologically active compounds.
Used in Polymer Production:
(1S,2S)-1,2-BIS(2,4,6-TRIMETHYLPHENYL)ETHYLENEDIAMINE is utilized in the production of polymers, where its unique structure and properties contribute to the development of materials with specific characteristics.
Used as a Chiral Resolving Agent in Analytical Chemistry:
In the field of analytical chemistry, (1S,2S)-1,2-BIS(2,4,6-TRIMETHYLPHENYL)ETHYLENEDIAMINE serves as a chiral resolving agent, helping to separate enantiomers and analyze their properties, which is vital for understanding the stereochemistry of molecules and their interactions.

InChI:InChI=1/C20H28N2/c1-11-7-13(3)17(14(4)8-11)19(21)20(22)18-15(5)9-12(2)10-16(18)6/h7-10,19-20H,21-22H2,1-6H3/t19-,20-/m0/s1

Upstream product

• 58519-81-6 C₃₄H₃₆N₂O₂ 
• 1301706-47-7 (S,S)-1,2-bis(2,4,6-trimethylphenyl)-1,2-diaminoethane dihydrochloride 

Downstream Products

• 1620379-98-7 C₂₅H₃₆N₂O₂ 

Relevant articles and documents

Stereospecific diaza-cope rearrangement driven by steric strain

(Chemical Equation Presented) Bucklingunder the strain: Steric strain was used to drive the diaza-Cope rearrangement to completion (see scheme) with a high degree of stereospecificity (>99.5% ee), as evidenced by chiral-phase HPLC and crystal data. There is good agreement between the experimental and computational values for the rate and equilibrium constants for the rearrangement.

IMIDAZOLIDINE-BASED METAL CARBENE METATHESIS CATALYSTS

The present invention relates to novel metathesis catalysts with an imidazolidine-based ligand and to methods for making and using the same. The inventive catalysts are of formula (I) wherein : M is ruthemium or osmium; X and X are each independently an anionic ligand; L is a neutral electron donor ligand; and, R, R, R, R, R and R are each independently hydrogen or a substituent selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, aryloxy, C2-C20 alkoxycarbonyl, C1-C20 alkylthiol, aryl thiol, C1-C20 alkylsulfonyl and C1-C20 alkylsulfinyl, the substituent optionally substituted with one or more moieties selected from the group consisting of C1-C10 alkyl, C1-C10 alkoxy, aryl, and a functional group selected from the group consisting of hydroxyl, thiol thioether, ketone, aldehyde, ester, ether, amine, imine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carbodiimide, carboalkoxy, carbamate, and halogen. The inclusion of an imidazolidine ligand to the previously described ruthenium or osmium catalysts has been found to dramatically improve the properties of theses complexes. The inventive catalysts maintains the functional group tolerance of previously described ruthenium complexes while having enhanced metathesis activity that compares favorably to prior art tungsten and molybdenum systems.

Efficient preparation of C2-symmetrical chiral ferrocenyl diols by catalytic enantioselective reduction of diacylferrocenes

equation presented Enantioselective borohydride reduction, catalyzed by the optically active β-ketoiminato cobalt(III) complex, was successfully applied to the 1,1′-dialkanoyl- and 1,1′-dibenzoylferrocenes to afford the corresponding C2-symmetr