(R,R)-TsDPEN

Base Information

• Chemical Name: (R,R)-TsDPEN
• CAS No.: 144222-34-4
• Molecular Formula: C21H22N2O2S
• Molecular Weight: 366.484
• Hs Code.: 29215900
• European Community (EC) Number: 625-751-7
• DSSTox Substance ID: DTXSID70370363
• Nikkaji Number: J1.107.181C
• Mol file: 144222-34-4.mol

Synonyms:Benzenesulfonamide,N-(2-amino-1,2-diphenylethyl)-4-methyl-, [R-(R*,R*)]-;(1R,2R)-(-)-N-(4-Toluenesulfonyl)-1,2-diphenylethylene-1,2-diamine;(1R,2R)-(-)-N-(p-Tolylsulfonyl)-1,2-diphenylethylenediamine;(1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine;(1R,2R)-1-Amino-2-tosylamino-1,2-diphenylethane;(1R,2R)-N-p-Toluenesulfonyl-1,2-diphenylethylenediamine;(R,R)-1,2-Diphenyl-N-(p-toluenesulfonyl)ethylenediamine;(R,R)-N-(p-Toluenesulfonyl)-1,2-diphenylethylenediamine;N-[(1R,2R)-2-Amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide;[(1R,2R)-1,2-Diphenyl-2-[[(4-tolyl)sulfonyl]amino]ethyl]amine;

Chemical Property of (R,R)-TsDPEN

Chemical Property:

• Appearance/Colour: white or pale yellow needle crystalline
• Vapor Pressure: 1.28E-11mmHg at 25°C
• Melting Point: 128-131 °C(lit.)
• Refractive Index: -30 ° (C=0.4, CHCl3)
• Boiling Point: 537.3 °C at 760 mmHg
• PKA: 10.76±0.50(Predicted)
• Flash Point: 278.8 °C
• PSA: 80.57000
• Density: 1.224 g/cm³
• LogP: 5.88660
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform, Methanol
• Water Solubility.: insoluble
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 366.14019912
• Heavy Atom Count: 26
• Complexity: 511

Purity/Quality:

99% ^*data from raw suppliers

(R,R)-N-(2-Amino-1,2-diphenylethyl)-p-toluenesulfonamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC(C2=CC=CC=C2)C(C3=CC=CC=C3)N
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)N[C@H](C2=CC=CC=C2)[C@@H](C3=CC=CC=C3)N
• Uses: (1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine is used as a catalyst in stereoselective preparation of aromatic ketone derivatives as well as other chiral organic compounds. Chiral diamine ligand for cooperative metal-Bronsted acid catalyzed greener reductive amination using hydrogen gas.Metal-Br?nsted Acid Cooperative Catalysis for Asymmetric Reductive Amination

Technology Process of (R,R)-TsDPEN

There total 2 articles about (R,R)-TsDPEN which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

(R,R)-1,2-diphenylethylenediamine (35132-20-8) + p-toluenesulfonyl chloride (98-59-9) → (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (144222-34-4)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 12h;

DOI:10.1016/j.tetlet.2008.04.130

Reference yield:

(1S,2S)-N-(p-tolylsulfonyl)-1,2-diphenylethylenediamine → N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide (167316-27-0) + (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (144222-34-4)

Guidance literature:

With chiral stationary phase including propylsulfonate-functionalized CF₆; In methanol; acetic acid; acetonitrile; Purification / work up;

Reference yield: 99.0%

(R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (144222-34-4) → N-(2-azido-1,2-diphenylethyl)-4-methylbenzenesulfonamide

Guidance literature:

With fluorosulfonyl azide; potassium hydrogencarbonate; In tert-butyl methyl ether; water; N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h;

DOI:10.1038/s41586-019-1589-1

upstream raw materials:

(R,R)-1,2-diphenylethylenediamine

p-toluenesulfonyl chloride

Downstream raw materials:

N-(1R,2R)-[2-(3-cyclohexa-1,4-dienyl-propylamino)-1,2-diphenyl-ethyl]-4-methyl-benzene sulphonamide

[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

Refernces

• 1、 -. "A four-hydrogenated 1, 8 - naphthyridine apperception composition preparation method and its prepared chiral products". Paragraph 0137. . Retrieved 2018/03/26.
• 2、 -. "A four-hydrogenated 1, 5 - naphthyridine apperception composition preparation method and its prepared chiral products". Paragraph 0138. . Retrieved 2017/08/25.