(1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine CAS 144222-34-4
Introduction：Basic information about (1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine CAS 144222-34-4, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
(1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine Basic information
| Product Name: | (1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine |
| 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-Tosyl-1,2-diphenylethylenediamine;(1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine98%;(R,R)-Ts-DPEN, (1R,2R)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine, 98%;Benzenesulfonamide,N-[(1R,2R)-2-amino-1,2-diphenylethyl]-4-methyl-;(1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine≥ 99% (Assay, Chiral purity) |
| CAS: | 144222-34-4 |
| MF: | C21H22N2O2S |
| MW: | 366.48 |
| EINECS: | |
| Product Categories: | Chiral Nitrogen;DPEN Series;organic amine;chiral;API intermediates;Chiral Compound;Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents;HydrogenationChiral Building Blocks;Organic Building Blocks;Polyamines;Asymmetric Synthesis;Synthetic Organic Chemistry |
| Mol File: | 144222-34-4.mol |
(1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine Chemical Properties
| Melting point | 128-131 °C(lit.) |
| alpha | -61.5 º (c=1, CH2Cl2) |
| Boiling point | 537.3±60.0 °C(Predicted) |
| density | 1.1440 (rough estimate) |
| 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) |
| form | Crystals or Crystalline Powder |
| color | White to slightly yellow |
| Optical Rotation | [α]20/D 35°, c = 1 in chloroform |
| Water Solubility | insoluble |
| InChI | InChI=1S/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/t20-,21-/m1/s1 |
| InChIKey | UOPFIWYXBIHPIP-NHCUHLMSSA-N |
| SMILES | C1(S(N[C@H](C2=CC=CC=C2)[C@H](N)C2=CC=CC=C2)(=O)=O)=CC=C(C)C=C1 |
| CAS DataBase Reference | 144222-34-4(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 3 |
| HS Code | 29215900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Chemical Properties | white to slightly yellow crystals or crystalline |
| 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. |
| Uses | 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 |
| General Description | This product has been enhanced for catalytic efficiency. |
| Synthesis | 35132-20-8 98-59-9 144222-34-4 (1) (R,R)-1,2-diphenylethylenediamine (20 mmol) was dissolved in dichloromethane (30 mL) and cooled to 0°C in an ice bath. A solution of p-toluenesulfonyl chloride (20 mmol) dissolved in dichloromethane (30 mL) was slowly added dropwise to the above solution at 0 °C (dropwise time 30 min). After the dropwise addition was completed, the reaction was continued at 0°C for 1 hour. After completion of the reaction, the solvent was removed by concentration under reduced pressure by rotary evaporator to obtain the crude product. The crude product was purified by column chromatography (eluent: dichloromethane/methanol=10:1, v/v) to afford the target product (R,R)-(-)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (15 mmol) in 75% yield. |
| References | [1] Tetrahedron Letters, 2008, vol. 49, # 27, p. 4289 - 4291 [2] European Journal of Organic Chemistry, 2000, # 12, p. 2247 - 2252 [3] Tetrahedron Asymmetry, 2009, vol. 20, # 6-8, p. 910 - 920 [4] Molecules, 2010, vol. 15, # 4, p. 2551 - 2563 [5] Patent: CN107286089, 2017, A. Location in patent: Paragraph 0078; 0148-0149 |
(1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine Preparation Products And Raw materials
| Raw materials | (1R,2R)-(+)-1,2-Diphenylethylenediamine-->Tosyl chloride |
