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| | 3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE Basic information |
| Product Name: | 3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE | | Synonyms: | 3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE;1,2-CYCLOPROPANE DICARBOXYLIC ANHYDRIDE;3-Oxabicyclo[3.1.0]hexane-2,4-dione, 2,4-Dioxo-3-oxabicyclo[3.1.0]hexane;Cyclopropane-1,2-dicarboxylic acid anhydride;CYCLOPROPANE-2,3 DICARBOXYLIC ACID ANHYDRIDE;3-Oxabicyclo[3.1.0]hexane-2,4-dione,98%;3-Oxabicyclo[3.1.]hexane-2,4-dione;3-Oxabicyclo[3.1.0]hexane-2,4-dione, 97+% | | CAS: | 5617-74-3 | | MF: | C5H4O3 | | MW: | 112.08 | | EINECS: | 690-462-5 | | Product Categories: | Cycloalkanes | | Mol File: | 5617-74-3.mol | ![3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE Structure](CAS/GIF/5617-74-3.gif) |
| | 3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE Chemical Properties |
| Melting point | 59-61 °C(lit.) | | Boiling point | 100-102 °C5 mm Hg(lit.) | | density | 1.50 | | refractive index | 1.4630 (estimate) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble in Methanol | | form | Powder, Crystals and/or Chunks | | color | White to off-white | | Sensitive | Moisture Sensitive | | InChI | InChI=1S/C5H4O3/c6-4-2-1-3(2)5(7)8-4/h2-3H,1H2 | | InChIKey | ZRMYHUFDVLRYPN-UHFFFAOYSA-N | | SMILES | C12C(C1)C(=O)OC2=O | | CAS DataBase Reference | 5617-74-3 |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 37/39-26 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29329900 | | Storage Class | 11 - Combustible Solids |
| | 3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE Usage And Synthesis |
| Chemical Properties | white crystals or crystalline powder | | Uses | 3-Oxabicyclo[3.1.0]hexan-2,4-dione is used as a reagent in synthesis of several organic compounds including that of a newly discovered histamine H3 receptor inverse agonist that enhances short term memory. Also used in the synthesis of phthalazinone derivatives which act as topically active phosphodiesterase 4 inhibitors. | | Synthesis | In a 500 mL three-necked flask, cyclopropane-1,2-dicarboxylic acid (130 g, 1 mol) was mixed with acetic anhydride (255 g, 2.5 mol) and heated in an oil bath to about 140 °C and kept at reflux while mechanically stirring. After 2 hours of reflux reaction, the mixture of acetic acid and acetic anhydride was slowly added and the temperature was gradually raised to 220°C. At this temperature, the reaction was continued for 1 hour. Upon completion of the reaction, the mixture was cooled to about 120 °C, followed by vacuum distillation (1 mmHg, 106-108 °C) to purify the product to afford 3-oxabicyclo[3.1.0]hexane-2,4-dione (87 g, GC purity: 99.82%, yield: 81%). The product was white crystal with the melting point of 56-58 °C (literature value: 54-56 °C).1H-NMR (300 MHz, DMSO-d6) data were as follows: δ 2.90-2.94 (2H, m), 1.81-1.85 (1H, m), 1.59-1.67 (1H, m). | | References | [1] Tetrahedron Asymmetry, 1996, vol. 7, # 11, p. 3169 - 3180
[2] Letters in Organic Chemistry, 2015, vol. 12, # 10, p. 741 - 744 |
| | 3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE Preparation Products And Raw materials |
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