(S)-(+)-Glycidyl nosylate CAS 115314-14-2
(S)-(+)-Glycidyl nosylate Basic information
| Product Name: | (S)-(+)-Glycidyl nosylate |
| Synonyms: | (2S)-OxiranylMethyl 3-Nitrobenzenesulfonate;(S)-Oxiran-2-ylMethyl 3-nitrobenzenesulfonate;(S)-(+)-Glycidyl nosylate, >=98.5%;Glycidyl (S)-(+)-3-nitrobenzenesulfonate;(S)-Glycidyl Nosylate,98%e.e.;(S)-(+)-OXIRANE-2-METHANOL 3-NITROBENZENESULFONATE;(S)-(+)-GLYCIDYL 3-NITROBENZENESULFONATE;(S)-GLYCIDYL 3-NITROBENZENESULFONATE |
| CAS: | 115314-14-2 |
| MF: | C9H9NO6S |
| MW: | 259.24 |
| EINECS: | 621-475-6 |
| Product Categories: | chiral;CHIRAL COMPOUNDS;APIs Intermediate;Chiral Reagents;Heterocycles;Sulfur & Selenium Compounds |
| Mol File: | 115314-14-2.mol |
(S)-(+)-Glycidyl nosylate Chemical Properties
| Melting point | 61-65 °C |
| alpha | 21.5 º (c=2, CHCl3) |
| Boiling point | 432.2±20.0 °C(Predicted) |
| density | 1.5881 (rough estimate) |
| refractive index | 1.5270 (estimate) |
| storage temp. | Inert atmosphere,2-8°C |
| solubility | Soluble in chloroform, methylene chloride and tetrahydrofuran. Insoluble in hexane. |
| form | Needles or Powder |
| color | Off-white to yellow-brown |
| Sensitive | Moisture Sensitive |
| InChI | InChI=1S/C9H9NO6S/c11-10(12)7-2-1-3-9(4-7)17(13,14)16-6-8-5-15-8/h1-4,8H,5-6H2/t8-/m0/s1 |
| InChIKey | AIHIHVZYAAMDPM-QMMMGPOBSA-N |
| SMILES | C1(S(OC[C@@H]2CO2)(=O)=O)=CC=CC([N+]([O-])=O)=C1 |
| CAS DataBase Reference | 115314-14-2(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38-5 |
| Safety Statements | 37/39-26-36 |
| RIDADR | UN 1325 4.1/PG II |
| RTECS | DB7192010 |
| HazardClass | 4.1 |
| PackingGroup | II |
| HS Code | 29209090 |
| Uses | (S)-(+)-Glycidyl Nosylate is a compound useful in organic synthesis. |
| Chemical Properties | white to light yellow crystal powde |
| Uses | (S)-(+)-Glycidyl Nosylate (cas# 115314-14-2) is a compound useful in organic synthesis. |
| Synthesis | 121-51-7 57044-25-4 115314-14-2 General procedure for the synthesis of (S)-(+)-m-nitrobenzenesulfonic acid glycidyl ester from 3-nitrobenzenesulfonyl chloride and (R)-oxirane-2-methanol: at -20 °C, m-nitrobenzenesulfonyl chloride (12.6 g, 57 mmol) was slowly added to a solution containing (R)-(+)-glycidol (5.5 g, 74 mmol) and triethylamine (TEA, 10.3 mL. 74 mmol) in a cold solution. The reaction mixture was stirred continuously at -20 °C for 96 hours. Upon completion of the reaction, the reaction solution was filtered and the filtrate was washed sequentially with 10% (w/w) aqueous tartaric acid, saturated saline and deionized water. The washed organic phase was concentrated to afford the target product (S)-(+)-m-nitrobenzenesulfonic acid glycidyl ester in 97% yield. The structure of the product was confirmed by 1H NMR (CDCl3): δ 2.62 (dd, 1H), 2.84 (dd, 1H), 3.22 (m, 1H), 4.07 (dd, 1H), 4.49 (dd, 1H), 7.80 (t, 1H), 8.25 (m, 1H), 8.52 (m, 1H), 8.78 (m, 1H). |
| References | [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 20, p. 5305 - 5308 [2] Angew. Chem., 2013, vol. 125, # 20, p. 5413 - 5416,4 [3] European Journal of Organic Chemistry, 2014, vol. 2014, # 19, p. 4053 - 4069 [4] Patent: US2004/229900, 2004, A1. Location in patent: Page 14 [5] Organic and Biomolecular Chemistry, 2006, vol. 4, # 16, p. 3067 - 3076 |
(S)-(+)-Glycidyl nosylate Preparation Products And Raw materials
| Raw materials | 3-Nitrobenzenesulfonyl chloride-->(S)-Oxiranemethanol-->(R)-(+)-Glycidol |
| Preparation Products | (S)-2-Oxiranylanisole |
