| Identification | More | [Name]
6,7-Dihydro-4(5H)-benzofuranone | [CAS]
16806-93-2 | [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% | [Molecular Formula]
C8H8O2 | [MDL Number]
MFCD00215511 | [Molecular Weight]
136.15 | [MOL File]
16806-93-2.mol |
| Chemical Properties | Back Directory | [Appearance]
clear yellow to brown low melting solid or liquid | [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 | [color ]
Clear yellow to brown | [Specific Gravity]
1.162 | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HS Code ]
29143900 |
| Hazard Information | Back Directory | [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 |
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