144222-34-4

Basic information

• Product Name: (R,R)-TsDPEN
• Synonyms: (R,R)-N-(P-TOLUENESULFONYL)-1,2-DIPHENYLETHYLENEDIAMINE;(R,R)-N-(2-AMINO-1,2-DIPHENYLETHYL)-P-TOLUENESULFONAMIDE;(R,R)-TSDPEN;(1R,2R)-N-(P-TOLUENESULFONYL)-1,2-DIPHENYL-1,2-ETHANEDIAMINE;(1R,2R)-TSDPEN;(1R,2R)-(-)-N-P-TOSYL-1,2-DIPHENYLETHYLENEDIAMINE;(1R, 2R)-(-)-N-(4-TOLUENE SULFONYL)1,2-DIPHENYL-1,2-ETHANE DIAMINE;(1R,2R)-(-)-N-(4-TOLUENESULFONYL)-1,2-DIPHENYLETHYLENEDIAMINE
• CAS NO: 144222-34-4
• Molecular Formula: C₂₁H₂₂N₂O₂S
• Molecular Weight: 366.48
• Product Categories: chiral;API intermediates;Asymmetric Synthesis;Synthetic Organic Chemistry;Chiral Compound;Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents;HydrogenationChiral Building Blocks;Organic Building Blocks;Polyamines;organic amine;Chiral Nitrogen;DPEN Series
• Mol File: 144222-34-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 128-131 °C(lit.)
• Boiling Point: 537.3 °C at 760 mmHg
• Flash Point: 278.8 °C
• Appearance: White to slightly yellow/Crystals or Crystalline Powder
• Density: 1.1440 (rough estimate)
• Vapor Pressure: 1.28E-11mmHg at 25°C
• Refractive Index: -30 ° (C=0.4, CHCl3)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform, Methanol
• PKA: 10.76±0.50(Predicted)
• Water Solubility: insoluble
• CAS DataBase Reference: (R,R)-TsDPEN(CAS DataBase Reference)
• NIST Chemistry Reference: (R,R)-TsDPEN(144222-34-4)
• EPA Substance Registry System: (R,R)-TsDPEN(144222-34-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 144222-34-4(Hazardous Substances Data)

Usage

Description

(R,R)-TsDPEN, also known as (1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine, is a chiral diamine ligand that has been enhanced for catalytic efficiency. It appears as white to slightly yellow crystals or crystalline in its chemical form. (R,R)-TsDPEN plays a significant role in various chemical reactions and processes due to its unique stereochemistry and reactivity.

Uses

Used in Pharmaceutical Industry:
(R,R)-TsDPEN is used as a catalyst for the stereoselective preparation of aromatic ketone derivatives and other chiral organic compounds. Its application in this industry is crucial for the synthesis of enantiomerically pure compounds, which are essential in the development of drugs with improved efficacy and reduced side effects.
Used in Chemical Synthesis:
(R,R)-TsDPEN serves as a chiral diamine ligand in cooperative metal-Bronsted acid catalyzed greener reductive amination using hydrogen gas. This application is particularly important in the synthesis of chiral amines, which are key building blocks in the pharmaceutical, agrochemical, and fine chemical industries. The use of (R,R)-TsDPEN in this process allows for more efficient and environmentally friendly production of these valuable compounds.
Used in Asymmetric Reductive Amination:
(R,R)-TsDPEN is employed as a chiral ligand in the metal-Bronsted acid cooperative catalysis for asymmetric reductive amination. This process is vital for the production of enantiomerically enriched amines, which are widely used in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals. The use of (R,R)-TsDPEN in this reaction provides a more selective and efficient method for obtaining the desired chiral products.

InChI:InChI=1/C21H22N2O2S/c1-16-12-14-19(15-13-16)26(24,25)23-21(18-10-6-3-7-11-18)20(22)17-8-4-2-5-9-17/h2-15,20-21,23H,22H2,1H3/p+1/t20-,21-/m1/s1

Upstream product

• 35132-20-8 (R,R)-1,2-diphenylethylenediamine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 851051-41-7 N-(1R,2R)-[2-(3-cyclohexa-1,4-dienyl-propylamino)-1,2-diphenyl-ethyl]-4-methyl-benzene sulphonamide 
• 192139-90-5 [N-[(1R,2R)-2-(amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2, 3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]-ruthenium 
• 556025-95-7 (S)-2-(1-hydroxy-2-chloroethyl)-thiophene 
• 191592-36-6 (+)-5-[3-[4-(4-fluorophenyl)piperazin-1-yl]propyl]-8-hydroxy-1-methyl-1,4,5,6,7,8-hexahydropyrrolo[3,2-c]azepin-4-one 
• 1674-30-2 1-phenyl-2-chloroethanol 
• 141303-28-8 2-chloro-1-(m-tolyl)ethan-1-ol 

Relevant articles and documents

Synthesis of simple enantiopure tetrahydro-β-carbolines and tetrahydroisoquinolines

Enantioselective hydrogenation of the imines 11-13, 27 and 30 with the Ru complex (R,R)-5 led to the tetrahydro-β-carbolines (1S)-14, (1R)-21 and (1S)-22, and the tetrahydroisoquinoline (1S)-31 with ee > 95%. By employing (S,S)-5 the enantiomers are accessible. The imines 11-12 and 27 were obtained by oxidation of racemic 14, 21 and 22 with KMnO4 in > 58% yield.

O-bicyclic amine compounds as well as preparation method and chiral products thereof

The invention relates to the field of asymmetric synthesis methods, and discloses a preparation method of o-bicyclic amine compounds. The method comprises the step of enabling a compound having a structure as shown in a formula (1) and hydrogen to be subjected to an addition reaction in presence of a chiral catalyst, wherein the chiral catalyst is a complex having a structure as shown in a formula (2). The invention also provides chiral products of the o-bicyclic amine compounds prepared by the method, and the o-bicyclic amine compounds. After the method is adopted, the selective hydrogenation reduction of the compound having the structure as shown in the formula (1) is realized by using the hydrogen, so that octahydrogenated products, i.e., the o-bicyclic amine compounds shown in a formula (4) are produced with low cost. The formula (1), the formula (2) and the formula (4) are described in the description.

(1R,2R)-(+)-(1,2)-DPEN-Bonded Sulfonic Acid Resin: A Trifunctional Heterogeneous Catalyst for Asymmetric Michael Additions of Acetone to Nitroolefins

Based on (1R,2R)-(+)-(1,2)-DPEN skeleton, a series of primary amine-sulfamide bifunctional catalysts were synthesized, which exhibited excellent catalytic performance in the Michael addition of acetone to β-nitrostyrene. Therefore, a trifunctional heterogeneous catalyst was designed and prepared by simple N-sulfonyl reaction of (1R,2R)-(+)-(1,2)-DPEN and sulfonyl chloride resin. It was employed for the aforementioned addition without any additive and satisfactory results (80.5% conversion; 84.3% ee) were obtained. Meanwhile, the structural and textural properties of the catalyst were characterized by infrared spectroscopy (FT-IR), elemental analysis, SEM, and N2 adsorption and desorption experiments. Finally, the generality of the catalyst was investigated.