(R)-(+)-4-Isopropyl-2-oxazolidinone CAS 95530-58-8
(R)-(+)-4-Isopropyl-2-oxazolidinone Basic information
| Product Name: | (R)-(+)-4-Isopropyl-2-oxazolidinone |
| Synonyms: | (R)-(+)-4-ISOPROPYL-2-OXAZOLIDINONE;(R)-4-ISOPROPYL-2-OXAZOLIDINONE;(4R)-4-ISOPROPYL-1,3-OXAZOLIDIN-2-ONE;(4R)-(+)-4-ISOPROPYL-2-OXAZOLIDINONE;(4R)-(+)-ISOPROPYL-2-OXAZOLIDINONE;4-R-ISOPROPYL-OXAZOLIDIN-2-ONE;(R)-4-Isopropyl-2-oxazolidinone;-4-Isopropyloxazolidin-2-one |
| CAS: | 95530-58-8 |
| MF: | C6H11NO2 |
| MW: | 129.16 |
| EINECS: | |
| Product Categories: | Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives;chiral;Asymmetric Synthesis;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry;Peptide;Oxazolidinone;Pyrazoles,Pyrazines |
| Mol File: | 95530-58-8.mol |
(R)-(+)-4-Isopropyl-2-oxazolidinone Chemical Properties
| Melting point | 70-73 °C |
| alpha | -18 º (c=1, ethanol) |
| Boiling point | 239.22°C (rough estimate) |
| density | 1.04 g/cm3 |
| refractive index | 1.4300 (estimate) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | very faint turbidity in EtOH |
| pka | 12.72±0.40(Predicted) |
| form | Crystalline Powder |
| color | White |
| Optical Rotation | [α]20/D +17°, c = 6 in ethanol |
| Water Solubility | Soluble |
| BRN | 5376658 |
| InChI | InChI=1S/C6H11NO2/c1-4(2)5-3-9-6(8)7-5/h4-5H,3H2,1-2H3,(H,7,8)/t5-/m0/s1 |
| InChIKey | YBUPWRYTXGAWJX-YFKPBYRVSA-N |
| SMILES | O1C[C@@H](C(C)C)NC1=O |
| CAS DataBase Reference | 95530-58-8(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 22-24/25-36-26 |
| WGK Germany | 3 |
| F | 3 |
| HS Code | 29349990 |
| Chemical Properties | white to light yellow crystal powde |
| Uses | (R)-4-Isopropyloxazolidin-2-one is a biochemical reagent that can be used as a biological material or organic compound for life science related research. |
| Synthesis | 4276-09-9 124-38-9 95530-58-8 To a dry Schlenk tube containing DMSO-d6 (1 mL) and cesium carbonate (33 mg, 0.1 mmol) was added (S)-1a (0.1114 mL, 1 mmol). The reaction mixture was frozen in a liquid nitrogen bath (-196 °C), followed by evacuation to remove air and replacement with CO2 gas. After thawing to 25 °C, a balloon (1 L) containing CO2 was connected to the reaction tube. The reaction system was stirred at 150°C for 24 hours. Upon completion of the reaction, the crude product was analyzed by 1H NMR and the yield was calculated using the internal standard N,N-dimethylformamide as reference. Subsequently, DMSO-d6 was removed by distillation under reduced pressure conditions (6 mmHg, 50 °C).The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate, 3:1) to afford the target product (S)-4-isopropyloxazolidin-2-one ((S)-2a) as a white solid in 80% isolated yield (103.3 mg, 0.80 mmol). |
| References | [1] Journal of Organic Chemistry, 2000, vol. 65, # 15, p. 4759 - 4761 [2] Tetrahedron Letters, 2013, vol. 54, # 35, p. 4717 - 4720 |
(R)-(+)-4-Isopropyl-2-oxazolidinone Preparation Products And Raw materials
| Raw materials | (R)-(-)-2-Amino-3-methyl-1-butanol-->DL-2-AMINO-3-METHYL-1-BUTANOL-->ACETYLUREA-->Cesium carbonate-->Dimethyl sulfoxide-d6-->carbon monoxide-->Carbon dioxide-->1,1'-Carbonyldiimidazole-->Diethyl carbonate-->Isovaleraldehyde |
| Preparation Products | (4S)-(-)-4-Isopropyl-2-oxazolidinone-->(S)-(+)-4-Isopropyl-3-propionyl-2-oxazolidinone-->(S)-(+)-Ibuprofen-->Naproxen |
