| Identification | Back Directory | [Name]
3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE | [CAS]
5617-74-3 | [Synonyms]
3-Oxabicyclo[3.1.]hexane-2,4-dione
3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE
1,2-CYCLOPROPANE DICARBOXYLIC ANHYDRIDE
3-Oxabicyclo[3.1.0]hexane-2,4-dione,98%
3-Oxabicyclo[3.1.0]hexane-2,4-dione, 97+%
CYCLOPROPANE-2,3 DICARBOXYLIC ACID ANHYDRIDE
Cyclopropane-1,2-dicarboxylic acid anhydride
3-Oxabicyclo[3.1.0]hexane-2,4-dione, 2,4-Dioxo-3-oxabicyclo[3.1.0]hexane | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C5H4O3 | [MDL Number]
MFCD00126929 | [MOL File]
5617-74-3.mol | [Molecular Weight]
112.08 |
| Chemical Properties | Back Directory | [Appearance]
white crystals or crystalline powder | [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 Information | Back Directory | [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 |
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