167316-27-0

Basic information

• Product Name: (1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine
• Synonyms: (S,S)-N-(P-TOLUENESULFONYL)-1,2-DIPHENYLETHYLENEDIAMINE;(S,S)-TSDPEN;(1S, 2S)-(+)-N-(4-TOLUENE SULFONYL)1,2-DIPHENYL-1,2-ETHANE DIAMINE;(1S,2S)-N-(4-TOLUENESULFONYL)-1,2-DIPHENYLETHYLENE-1,2-DIAMINE;(1S,2S)-(+)-N-(4-TOLUENESULFONYL)-1,2-DIPHENYLETHYLENEDIAMINE;(1S,2S)-(+)-N-(4-TOLUENESULPHONYL)-1,2-DIPHENYLETHYLENEDIAMINE;(1S,2S)-TSDPEN;(1S,2S)-N-(P-TOLUENESULFONYL)-1,2-DIPHENYL-1,2-ETHANEDIAMINE
• CAS NO: 167316-27-0
• Molecular Formula: C₂₁H₂₂N₂O₂S
• Molecular Weight: 366.48
• Product Categories: API intermediates;Asymmetric Synthesis;Synthetic Organic Chemistry;Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents;HydrogenationChiral Building Blocks;Organic Building Blocks;Polyamines;organic amine;Chiral Nitrogen;DPEN Series
• Mol File: 167316-27-0.mol
• Article Data: 15

Chemical Properties

• Melting Point: 128-131 °C(lit.)
• Boiling Point: 537.3 °C at 760 mmHg
• Flash Point: 278.8 °C
• Appearance: white/crystal
• Density: 1.1440 (rough estimate)
• Vapor Pressure: 1.28E-11mmHg at 25°C
• Refractive Index: 30 ° (C=1, CHCl3)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Solubility in hot Acetonitrile (almost transparency).
• PKA: 10.76±0.50(Predicted)
• CAS DataBase Reference: (1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine(167316-27-0)
• EPA Substance Registry System: (1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine(167316-27-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 167316-27-0(Hazardous Substances Data)

Usage

Description

(1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine is a white to slightly yellow crystalline powder that has been enhanced for catalytic efficiency, adhering to the principles of greener chemistry. It is a versatile compound with applications in various industries due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
(1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine is used as a catalyst for the synthesis of keramamine C, a carboline alkaloid isolated from the Okinawan sponge Amphimedon sp. (1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine has potential applications in the development of new pharmaceuticals due to its unique chemical structure and properties.
Used in Medical Treatment:
In the medical field, (1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine is used as a catalyst in the synthesis of Tolvaptan (T536650), a selective oral vasopressin V2-receptor agonist. Tolvaptan is utilized for the treatment of hyponatremia, a condition characterized by low sodium levels in the blood, and the use of this catalyst aids in the efficient production of the drug.
Overall, (1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine is a valuable compound with applications in the pharmaceutical and medical industries, primarily as a catalyst in the synthesis of specific compounds. Its enhanced catalytic efficiency and adherence to greener chemistry principles make it a preferred choice for various chemical processes.

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-/m0/s1

Upstream product

• 530-36-9 (1S,2S)-2-amino-1,2-diphenylethanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 29841-69-8 (S,S)-1,2-diphenyl-1,2-diaminoethane 

Downstream Products

• 1043450-10-7 (1S,2S)-N-(1,2-diphenyl-2-(piperidin-1-yl)ethyl)-4-methyl-benzenesulfonamide 
• 1078693-61-4 4-methyl-N-((1S,2S)-2-(4-methylbenzylamino)-1,2-diphenylethyl)benzenesulfonamide 
• 958867-31-7 C₂₈H₂₈N₂O₂S 
• 1265177-67-0 2,2'-bis{N-[(1S,2S)-1,2-diphenyl-2-(4-methylbenzenesulfonamido)ethyl]carbamoyl}diphenyl sulfide 
• 1304189-57-8 N-heptyl TsDPEN 
• 1304189-39-6 N-methoxyethyl TsDPEN 
• 1304189-44-3 N-propyl TsDPEN 
• 1333982-28-7 4-methyl-N-((1S,2S)-2-(4-(4-methylcyclohexa-1,4-dienyl)butylamino)-1,2-diphenylethyl)benzenesulfonamide 
• 1404469-11-9 4-methyl-N-((1S,2S)-2-(4-(5-methylcyclohexa-1,4-dienyl)butylamino)-1,2-diphenylethyl)benzenesulfonamide 

Relevant articles and documents

Chiral nitrogen-metal complexes for the asymmetric reduction of ketones

Chiral cobalt-diamine complexes have been prepared and tested in catalytic reduction of β-ketoesters and ketones with molecular hydrogen or hydride transfer reduction (HTR). Modest to high conversions, but low e.e.s were obtained in the first case, wherea

2-[(2R, 6S)-6-[(2S)-2-hydroxy-2-phenethyl]-1-pipecoline]-1-hypnone synthesis method

The invention discloses a 2-[(2R, 6S)-6-[(2S)-2-hydroxy-2-phenethyl]-1-pipecoline]-1-hypnone synthesis method, and belongs to the field of organic synthesis. (1S, 2S)-1, 2-diphenyl diaminoethane serving as a raw material is subjected to acylation, substitution and the like to prepare chiral amine catalysts. A main route totally includes two steps: synthesizing glutaraldehyde, benzoyl acetic acid and methylamine hydrochloride to form cis-lobelanine; performing asymmetric selective reduction synthesis of 2-[(2R, 6S)-6-[(2S)-2-hydroxy-2-phenethyl]-1-pipecoline]-1-hypnone under mild reaction conditions and under the action of the catalysts. The raw material in the whole process route is cheap and easy to obtain, the catalysts can be recycled and can continue to be used, and the synthesis method is low in cost, simple in process, mild in reaction condition, convenient in operation and high in total yield.

L-Pipecolinic acid derived Lewis base organocatalyst for asymmetric reduction of N-aryl imines by trichlorosilane: Effects of the side amide group on catalytic performances

A series of N-formamides derived from pipecolinic acid have been synthesized and tested as Lewis base catalysts for the enantioselective reduction of N-aryl imines by trichlorosilane. Through the investigation of the structure-efficacy relationship between the side amide group and catalytic performance, several highly effective catalysts were discovered. In particular, arylamido-type catalyst 5i and non-arylamido-type catalyst 6c exhibited high reactivity and enantioselectivity, furnishing the reduction of a wide variety of N-aryl imines with high isolated yields (up to 98%) and ee values (up to 96%) under mild conditions. Moreover, these two catalysts complement each other in terms of their tolerances to nonaromatic ketimines and non-methyl ketimines. The Royal Society of Chemistry 2013.

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.