(S)-(+)-Glycidyl Phthalimide CAS 161596-47-0
Introduction：Basic information about (S)-(+)-Glycidyl Phthalimide CAS 161596-47-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
(S)-(+)-Glycidyl Phthalimide Basic information
| Product Name: | (S)-(+)-Glycidyl Phthalimide |
| Synonyms: | (S)-2-OXIRANYLMETHYL-ISOINDOLE-1,3-DIONE;(S)-(+)-GLYCIDYL PHTHALIMIDE;(S)-GLYCIDYL PHTHALIMIDE;2-[[(2S)-oxiran-2-yl]methyl]isoindole-1,3-dione;Rivaroxaban Impurity 39;2-((2S)-OXIRANYLMETHYL)-1H-ISOINDOLE-1,3(2H)-DIONE;(S)-(+)-N-(2,3-Epoxypropyl)phthalimide;(S)-N-Glycidylphthalimide |
| CAS: | 161596-47-0 |
| MF: | C11H9NO3 |
| MW: | 203.19 |
| EINECS: | 454-720-9 |
| Product Categories: | Intermediate of Rivaroxaban;N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides;Oxiranes;Simple 3-Membered Ring Compounds;bc0001 |
| Mol File: | 161596-47-0.mol |
(S)-(+)-Glycidyl Phthalimide Chemical Properties
| Melting point | 102 °C |
| Boiling point | 347.4±15.0 °C(Predicted) |
| density | 1.446±0.06 g/cm3(Predicted) |
| vapor pressure | 0.001-2.17Pa at 25-90.25℃ |
| refractive index | 10 ° (C=2.2, CHCl3) |
| storage temp. | under inert gas (nitrogen or Argon) at 2-8°C |
| solubility | Chloroform (Slightly), Ethyl Acetate (Slightly) |
| pka | -2.24±0.20(Predicted) |
| form | Solid |
| color | White |
| Optical Rotation | Consistent with structure |
| InChI | InChI=1S/C11H9NO3/c13-10-8-3-1-2-4-9(8)11(14)12(10)5-7-6-15-7/h1-4,7H,5-6H2/t7-/m0/s1 |
| InChIKey | DUILGEYLVHGSEE-ZETCQYMHSA-N |
| SMILES | C1(=O)C2=C(C=CC=C2)C(=O)N1C[C@H]1CO1 |
| LogP | 1.2 at 40℃ |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 41 |
| Safety Statements | 26-39 |
| WGK Germany | 2 |
| HS Code | 29252900 |
| Storage Class | 13 - Non Combustible Solids |
| Hazard Classifications | Eye Dam. 1 |
| Chemical Properties | White powder |
| Uses | (S)-(+)-Glycidyl Phthalimide is a phthalimide derivative used as an intermediate in the preparation of the antibiotic Linezolid (L466500). It is also a key intermediate of rivaroxaban. |
| Application | (S)-(+)-glycidyl phthalimide is primarily used as a key chiral intermediate in the synthesis of rivaroxaban, a structural unit for linezolid and antifungal thiazolidinones/oxazolidinones, a reference standard for rivaroxaban impurity 92 in quality control, and a chiral source for the synthesis of complex organic molecules with chiral hydroxyl/amino groups. |
| Synthesis | Phthalimide and (S)-1-substituent propylene oxide are used as raw materials, a reaction occurs under the action of a catalyst to generate 2-((S)-3-substituent-2-hydroxypropyl isodihydroindole-1,3-dione, and finally (S)-glycidyl phthalimide is generated by means of a ring-closure reaction. |
| References | [1] Patent: WO2004/112787, 2004, A1. Location in patent: Page 17-18 [2] Patent: WO2004/113301, 2004, A1. Location in patent: Page 18 [3] Tetrahedron Asymmetry, 1996, vol. 7, # 6, p. 1641 - 1648 [4] Heterocycles, 2006, vol. 67, # 2, p. 561 - 566 [5] Chemical communications (Cambridge, England), 2003, # 4, p. 468 - 469 |
(S)-(+)-Glycidyl Phthalimide Preparation Products And Raw materials
| Raw materials | (S)-2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione-->1H-Isoindol-1-one, 3-hydroxy--->(S)-Oxiranemethanol-->(S)-(+)-Epichlorohydrin-->(R)-(-)-Epichlorohydrin-->Potassium phthalimide-->(R)-(+)-Glycidol-->Triphenylphosphine-->Diethyl azodicarboxylate-->Tetrahydrofuran |
| Preparation Products | 2-[(2R)-2-Hydroxy-3-[[4-(3-oxo-4-Morpho linyl)phenyl]aMino]propyl]-1H-isoindole-1 ,3(2H)-dione |
