192139-90-5

Basic information

• Product Name: (S,S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine(chloro)(p-cymene)ruthenium(II)
• Synonyms: (S,S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine(chloro)(p-cymene)ruthenium(II);[N-[(1S,2S)-2-(Amino-KN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-KN]chloro[(1,2,3,4,5,6-η:)-1-methyl-4-(1-methylethyl)benzene]-ruthenium;RuCl(p-cymene)[(S,S)-Ts-DPEN];Chloro{[(1S,2S)-(+)-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido}(p-cymene)ruthenium(II);Chloro{[(1S,2S)-(+)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido}(p-cymene)ruthenium(II), min. 95%;Chloro{[(1S,2S)-(+)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido}(p-cymene)ruthenium(II), min. 95% RuCl[(S,S)-Tsdpen](p-cymene);[N-[(1S,2S)-2-(Amino-kN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-kN]chloro[(1,2,3,4,5,6-n)-1-methyl-4-(1-methylethyl)benzene]ruthenium;Chloro{[(1S,2S)-(+)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido}(p-cymene)ruthenium(II), min. 95% RuCl[(S,S)-Tsdpen](p-cymene)
• CAS NO: 192139-90-5
• Molecular Formula: C₃₁H₃₄ClN₂O₂RuS
• Molecular Weight: 631.17
• Product Categories: organometallic complex;Ru
• Mol File: 192139-90-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: >175 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: yellow to dark brown/solid
• Density: g/cm³
• Storage Temp.: 2-8°C
• Sensitive: air sensitive
• CAS DataBase Reference: (S,S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine(chloro)(p-cymene)ruthenium(II)(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine(chloro)(p-cymene)ruthenium(II)(192139-90-5)
• EPA Substance Registry System: (S,S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine(chloro)(p-cymene)ruthenium(II)(192139-90-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 192139-90-5(Hazardous Substances Data)

Usage

Description

(S,S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine(chloro)(p-cymene)ruthenium(II), also known as RuCl(p-cymene)[(S,S)-Ts-DPEN], is a chiral diamine ligand complexed with ruthenium. It is a solid compound that exhibits unique catalytic properties, making it a valuable component in various chemical reactions.

Uses

Used in Pharmaceutical Industry:
(S,S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine(chloro)(p-cymene)ruthenium(II) is used as a catalyst for asymmetric transfer hydrogenation of imines and ketones, which is crucial in the synthesis of enantiomerically pure pharmaceutical compounds. Its ability to selectively reduce imines and ketones to their corresponding amines and alcohols, respectively, with high enantioselectivity, makes it an essential tool in the development of new drugs.
Used in Chemical Research:
In the field of chemical research, (S,S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine(chloro)(p-cymene)ruthenium(II) is used as a catalyst for intramolecular asymmetric reductive amination. This reaction is vital for the synthesis of complex organic molecules, including natural products and biologically active compounds, as it allows for the formation of chiral amines with high enantiomeric purity.
Used in Petrochemical Industry:
(S,S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine(chloro)(p-cymene)ruthenium(II) is also employed as a catalyst in the tandem hydroformylation/hydrogenation of terminal olefins. This process is significant in the petrochemical industry for the production of valuable chemicals, such as aldehydes and alcohols, which serve as building blocks for various industrial applications.
Used in Material Science:
In material science, (S,S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine(chloro)(p-cymene)ruthenium(II) is utilized as a reactant in studies of thermal decomposition of arene-ruthenium chiral amido-amine alkyl complexes. Understanding the thermal stability and decomposition pathways of these complexes is crucial for the development of new materials and catalysts with improved performance and longevity.
Overall, (S,S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine(chloro)(p-cymene)ruthenium(II) is a versatile and valuable compound with applications spanning across various industries, including pharmaceuticals, chemical research, petrochemicals, and material science. Its unique catalytic properties and ability to facilitate enantioselective reactions make it an indispensable tool in the synthesis of complex organic molecules and the development of new materials.

Reaction

This catalyst has shown to effect highly enantioselective hydrogenation of functionalized ketones where the substituents are dialkylamino, hydoxy, siloxy, carbonyl, ester, amide or thioester.

InChI:InChI=1/C21H21N2O2S.C10H20.CH3.ClH.Ru/c1-16-12-14-19(15-13-16)25(24)26-23-21(18-10-6-3-7-11-18)20(22)17-8-4-2-5-9-17;1-8(2)10-6-4-9(3)5-7-10;;;/h2-15,20-22,24H,1H3;8-10H,4-7H2,1-3H3;1H3;1H;/q-2;;;;+3/p-1/t20-,21-;9-,10+;;;/m0..../s1/rC22H24ClN2O2RuS.C10H20/c1-17-13-15-20(16-14-17)27(26)29-25-22(19-11-7-4-8-12-19)21(24-28(25,2)23)18-9-5-3-6-10-18;1-8(2)10-6-4-9(3)5-7-10/h3-16,21-22,24,26H,1-2H3;8-10H,4-7H2,1-3H3/t21-,22-;9-,10+/m0./s1

Upstream product

• 52462-29-0 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 
• 144222-34-4 (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine 
• 167316-27-0 N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide 

Downstream Products

• 188444-43-1 [RuH(η⁶-p-cymene)(N-tosyl-1,2-diphenylethylenediamine)] 

Relevant articles and documents

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