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| | 6,7-Dihydro-4(5H)-benzofuranone Basic information |
| Product Name: | 6,7-Dihydro-4(5H)-benzofuranone | | Synonyms: | 6,7-DIHYDRO-1-BENZOFURAN-4(5H)-ONE;6,7-DIHYDRO-4(5H)-BENZOFURANONE;6,7-Dihydro-4(5H)-benzofuranone, GC 98%;6,7-DIHYDRO-4(5H)-BENZOFURANONE 98%;6,7-Dihydro-4(5H)-benzofuranone,98%;2,3-Dihydro-4(5H)-benzofuranone;6,7-dihydrobenzofuran-4(5H)-one;6,7-Dihydro-4(5H)-be | | CAS: | 16806-93-2 | | MF: | C8H8O2 | | MW: | 136.15 | | EINECS: | | | Product Categories: | Benzofurans;Building Blocks;Heterocyclic Building Blocks | | Mol File: | 16806-93-2.mol |  |
| | 6,7-Dihydro-4(5H)-benzofuranone Chemical Properties |
| Melting point | 30-34 °C (lit.) | | Boiling point | 115-118 °C/16 mmHg (lit.) | | density | 1.162 g/mL at 25 °C (lit.) | | refractive index | 1.53-1.532 | | Fp | >230 °F | | storage temp. | Sealed in dry,Store in freezer, under -20°C | | form | Liquid | | Specific Gravity | 1.162 | | color | Clear yellow to brown | | InChI | InChI=1S/C8H8O2/c9-7-2-1-3-8-6(7)4-5-10-8/h4-5H,1-3H2 | | InChIKey | DXWQOYPYNPSVRL-UHFFFAOYSA-N | | SMILES | O1C2CCCC(=O)C=2C=C1 | | CAS DataBase Reference | 16806-93-2(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 37/39-26 | | WGK Germany | 3 | | HS Code | 29143900 |
| | 6,7-Dihydro-4(5H)-benzofuranone Usage And Synthesis |
| Chemical Properties | clear yellow to brown low melting solid or liquid | | Uses | 6,7-Dihydro-4(5H)-benzofuranone may be used in the synthesis of furacridone ring skeleton. | | Definition | ChEBI: 6,7-Dihydro-4(5H)-benzofuranone is a member of benzofurans. | | Synthesis Reference(s) | Tetrahedron, 51, p. 3087, 1995 DOI: 10.1016/0040-4020(95)00070-O
Tetrahedron Letters, 27, p. 1127, 1986 DOI: 10.1016/S0040-4039(00)84195-7 | | General Description | 6,7-Dihydro-4(5H)-benzofuranone is a benzofuran derivative that consists of fused benzene and furan ring. Its standard molar enthalpy of formation by static bomb calorimetry and standard molar enthalpy of vaporization using Calvet microcalorimetry has been measured. These values have been used to derive the standard molar enthalpy of formation in gaseous phase. | | Synthesis | Under argon protection, 1,3-cyclohexanedione (20.71 g, 0.18 mol) was dissolved in methanol (100 mL) and the solution was cooled to 0 °C. Subsequently, potassium hydroxide (12.2 g, 0.18 mol) was added to the solution and stirred continuously for 30 minutes at 0 °C. Next, 50% aqueous chloroacetaldehyde solution (26.3 mL, 0.203 mol) was slowly added. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the solution was acidified to pH < 7 with 1N hydrochloric acid and then extracted with ethyl acetate. The organic layers were combined, washed sequentially with water and saturated saline, and dried over anhydrous magnesium sulfate. Finally, the solvent was removed by concentration under reduced pressure to give the crude 6,7-dihydro-4(5H)-benzofuranone product (16.5 g), which was pure enough to be used directly in the next step of the reaction. | | References | [1] Arkivoc, 2011, vol. 2011, # 9, p. 1 - 14
[2] Heterocycles, 2004, vol. 62, p. 807 - 813
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 4, p. 1966 - 1982
[4] Journal of Organic Chemistry, 1988, vol. 53, # 17, p. 4135 - 4137
[5] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 10, p. 2167 - 2169 |
| | 6,7-Dihydro-4(5H)-benzofuranone Preparation Products And Raw materials |
| Raw materials | 1,3-Cyclohexanedione, 2-diazo--->2-Furanbutanoyl chloride-->4(2H)-Benzofuranone, 3,5,6,7-tetrahydro-3-hydroxy--->3-hydroxycyclohex-2-en-1-one-->Chloroacetaldehyde-->1,4-Dimethoxybenzene-->Potassium hydroxide-->Methanol-->VINYLIDENE CHLORIDE-->1,3-Cyclohexanedione | | Preparation Products | Methyl 4-Oxo-4,5,6,7-Tetrahydrobenzofuran-5-Carboxylate |
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