121788-77-0

Basic information

• Product Name: (S,S)-N,N'-BIS(TRIFLUOROMETHANESULFONYL)-1,2-DIPHENYLETHYLENEDIAMINE
• Synonyms: (1S,2S)-N,N'-Bis(trifluoromethanesulfonyl)-1,2-diphenylet hylenediamine;(1S,2S)-N,N'-Bis(trifluoromethanesulfonyl)-1,2-diphenylet hylenediamine,99%e.e.;(S,S)-N,N'-BIS(TRIFLUOROMETHANESULFONYL)-1,2-DIPHENYLETHYLENEDIAMINE;(S,S)-N,N'-BIS(TRIFLUOROMETHYLSULFONYL)-1,2-DIPHENYLETHYLENEDIAMINE;(S,S)-1,2-BIS(TRIFLUOROMETHANESULFONAMIDO)-1,2-DIPHENYLETHANE;(S,S)-Bistrifluoromethanesulfonyldiphenylethylenediamine;N,N'-((1S,2S)-1,2-Diphenylethane-1,2-diyl)-bis(1,1,1-trifluoromethanesulfonamide)
• CAS NO: 121788-77-0
• Molecular Formula: C₁₆H₁₄F₆N₂O₄S₂
• Molecular Weight: 476.41
• Product Categories: Chiral Nitrogen;DPEN Series;Asymmetric Synthesis;Synthetic Organic Chemistry
• Mol File: 121788-77-0.mol

Chemical Properties

• Boiling Point: 484.6 °C at 760 mmHg
• Flash Point: 246.9 °C
• Appearance: /
• Density: 1.537 g/cm³
• Vapor Pressure: 1.51E-09mmHg at 25°C
• Refractive Index: 1.529
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: (S,S)-N,N'-BIS(TRIFLUOROMETHANESULFONYL)-1,2-DIPHENYLETHYLENEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-N,N'-BIS(TRIFLUOROMETHANESULFONYL)-1,2-DIPHENYLETHYLENEDIAMINE(121788-77-0)
• EPA Substance Registry System: (S,S)-N,N'-BIS(TRIFLUOROMETHANESULFONYL)-1,2-DIPHENYLETHYLENEDIAMINE(121788-77-0)

Safety Data

• Hazardous Substances Data: 121788-77-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
(S,S)-N,N'-Bis(trifluoromethanesulfonyl)-1,2-diphenylethylenediamine is used as a catalyst for facilitating specific chemical reactions. Its chiral nature allows it to selectively promote certain reactions, leading to the formation of desired products with high enantioselectivity and yield.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S,S)-N,N'-Bis(trifluoromethanesulfonyl)-1,2-diphenylethylenediamine is used as a catalyst for the synthesis of enantiomerically pure drugs. The ability to control the stereochemistry of the final product is crucial for ensuring the desired biological activity and minimizing potential side effects.
Used in Asymmetric Catalysis:
(S,S)-N,N'-Bis(trifluoromethanesulfonyl)-1,2-diphenylethylenediamine is employed as a chiral catalyst in asymmetric catalysis, a field that focuses on the development of enantioselective reactions. Its use in this area can lead to the production of optically active compounds with high selectivity, which are valuable in various applications, including the synthesis of chiral pharmaceuticals and agrochemicals.
Used in Research and Development:
In research and development, (S,S)-N,N'-Bis(trifluoromethanesulfonyl)-1,2-diphenylethylenediamine serves as a valuable tool for studying the mechanisms of enantioselective reactions and the development of new catalytic systems. Its unique properties can provide insights into the factors that govern stereoselectivity and help in the design of more efficient and selective catalysts for various applications.

InChI:InChI=1/C16H14F6N2O4S2/c17-15(18,19)29(25,26)23-13(11-7-3-1-4-8-11)14(12-9-5-2-6-10-12)24-30(27,28)16(20,21)22/h1-10,13-14,23-24H/t13-,14-/m0/s1

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 29841-69-8 (S,S)-1,2-diphenyl-1,2-diaminoethane 

Relevant articles and documents

Studies on a catalytic version of the Matteson asymmetric homologation reaction

Studies of a catalytic asymmetric version of the Matteson reaction between dichloromethylboronates and organolithium reagents have been undertaken. From several different chiral catalytic systems studied, only one based on a mannitol derivative has given substantial asymmetric induction close to that previously achieved with a bis(oxazoline) derivative and ytterbium triflate. More detailed study of the latter reaction revealed that fresh ytterbium triflate actually reduced the level of asymmetric induction, while "aged"ytterbium triflate, or a fresh sample that had been treated with water, brought about improved induction. The implications of these findings are discussed.

Convenient Routes to Symmetrical Benzils and Chiral 1,2-Diaryl-1,2-diaminoethanes, Useful Controllers and Probes for Enantioselective Synthesis

Pathways for the diastereoselective preparation of chiral 1,2-diaryl-1,2-diaminoethanes from ArCOOH, ArCHO or ArBr are described.