(1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine CAS 167316-27-0
(1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine Basic information
| Product Name: | (1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine |
| Synonyms: | (1S,2S)-(+)-N-p-Tosyl-1,2-diphenylethylenediamine;(S,S)-Ts-DPEN, (1S,2S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine, 98%;(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-diphenylethylenediaMine, 98% 500MG;(1S,2S)-(+)-N-p-Tosyl-1,2-diphenylethylenediamine≥ 99% (Assay, Chiral purity);(1S,2S)-N-p-Tosyl-1,2-diphenylethylenediamine,99%e.e. |
| CAS: | 167316-27-0 |
| MF: | C21H22N2O2S |
| MW: | 366.48 |
| EINECS: | |
| Product Categories: | Chiral Nitrogen;DPEN Series;API intermediates;Asymmetric Synthesis;Synthetic Organic Chemistry;Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents;HydrogenationChiral Building Blocks;Organic Building Blocks;Polyamines;organic amine |
| Mol File: | 167316-27-0.mol |
(1S,2S)-(+)-N-(4-Toluenesulfonyl)-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=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) |
| form | crystal |
| color | white |
| Optical Rotation | [α]20/D +35°, c = 1 in chloroform |
| 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-/m0/s1 |
| InChIKey | UOPFIWYXBIHPIP-SFTDATJTSA-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 | 167316-27-0(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 3 |
| HS Code | 29242990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Chemical Properties | White to slightly yellow crystalline powder |
| Uses | (1S,2S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine is used as a catalyst in the synthesis of keramamine C, a carboline alkaloid that is isolated from the Okinawan sponge Amphimedon sp. (1S,2S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine is also used as a catalyst in the synthesis of Tolvaptan (T536650), a selective oral vasopressin V2-receptor agonist that is used to treat hyponatremia. |
| 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 | We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information. |
| Synthesis | 29841-69-8 98-59-9 167316-27-0 Synthesis of Compound 2009: To a 2 L three-necked round-bottomed flask equipped with a temperature probe, magnetic stirring bar, nitrogen inlet, and constant-pressure dropping funnel was added (1S,2S)-1,2-diphenylethylenediamine (20 g, 0.094 mol) and dichloromethane (160 mL). The reaction mixture was cooled to 0-3 °C and 1 M sodium hydroxide solution (160 mL) was added slowly and dropwise while keeping the temperature below 5 °C. Subsequently, a solution of dichloromethane (320 mL) of p-toluenesulfonyl chloride (17.9 g, 0.094 mol) was added dropwise to the reaction system over a period of 2 hours. The biphasic reaction mixture was continued to be stirred at 0-5 °C for 1 h. Completion of the reaction was confirmed by thin layer chromatography (TLC, 50% ethyl acetate/heptane, UV detection). After completion of the reaction, the organic and aqueous phases were separated, and the organic phase was washed sequentially with water (2×320 mL) and saturated saline (320 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product. The crude product was dissolved in toluene (200 mL) at 70-80 °C, maintained at this temperature, and heptane (300 mL) was added in batches. The resulting slurry was cooled to 20-25 °C and stirred for 1 hour, then further cooled to 0-5 °C and stirred for 10 minutes. The solid was collected by filtration and washed with a heptane solution of 50% toluene (3 x 1 bed volume) to give compound 2009 (30.24 g, 88% yield) as a white powder. |
| References | [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2505 - 2511 [2] Journal of Organic Chemistry, 2004, vol. 69, # 4, p. 1283 - 1289 [3] Patent: WO2010/120719, 2010, A1. Location in patent: Page/Page column 194; 196-197 [4] Patent: CN106496099, 2017, A. Location in patent: Paragraph 0033; 0034; 0035; 0048; 0049 [5] Organic Syntheses, 2005, vol. 82, p. 10 - 17 |
(1S,2S)-(+)-N-(4-Toluenesulfonyl)-1,2-diphenylethylenediamine Preparation Products And Raw materials
| Raw materials | (1S,2S)-(-)-1,2-Diphenyl-1,2-ethanediamine-->Tosyl chloride-->Sodium hydroxide-->Dichloromethane |
