| Identification | More | [Name]
2-COUMARANONE | [CAS]
553-86-6 | [Synonyms]
2,3-DIHYDROBENZO[B]FURAN-2-ONE
2(3H)-BENZOFURANONE
2-COUMARANONE
2H-BENZOFURANONE
3H-BENZOFURAN-2-ONE
BENZOFURAN-2-ONE
BENZOFURANONE
ISOCOUMARANONE
1-Benzofuran-2(3H)-one
2-Coumaronone
2-Cumaranon
3H-Benzofuran-2-one~2,3-Dihydrobenzofuran-2-one
GIRARD'S REAGENT P 98%
2-Coumaranone,99%
2,3-dihydrobenzofuran-2-one
Benzo[b]furan-2(3H)-one
BENZOFURAN-2[3H]-ONE | [EINECS(EC#)]
209-052-0 | [Molecular Formula]
C8H6O2 | [MDL Number]
MFCD00005856 | [Molecular Weight]
134.13 | [MOL File]
553-86-6.mol |
| Chemical Properties | Back Directory | [Appearance]
WHITE TO LIGHT YELLOW CRYSTALLINE POWDER | [Melting point ]
49-51 °C(lit.)
| [Boiling point ]
248-250 °C(lit.)
| [density ]
1,22 g/cm3 | [vapor pressure ]
0.027-0.24Pa at 10-30℃ | [refractive index ]
1.4800 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
H2O: soluble3.8g/L at 30°C | [form ]
Crystalline Powder or Crystals | [color ]
White to yellow-orange | [Water Solubility ]
H2O: soluble 3.8g/L at30°C | [BRN ]
114689 | [InChI]
1S/C8H6O2/c9-8-5-6-3-1-2-4-7(6)10-8/h1-4H,5H2 | [InChIKey]
ACZGCWSMSTYWDQ-UHFFFAOYSA-N | [SMILES]
O=C1Cc2ccccc2O1 | [LogP]
1.347 | [Surface tension]
63.8mN/m at 1g/L and 20℃ | [CAS DataBase Reference]
553-86-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HS Code ]
29322090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
Skin Sens. 1 |
| Questions And Answer | Back Directory | [Description]
2-Coumaranone (also named as Isophthalide, 3H-benzofuran-2-one) belongs to a class of organic compounds named as benzofuranones which exhibits mutagenic and carcinogenic activity. 2-Coumaranone has been used to study the effects of coumarins on 7,12-dimethyibenz(a)anthracene induced neoplasia of the rat mammary gland and as probe for detecting enzymes which hydrolyze 2-hydroxybenzofuran structures.
| [Reference]
Y. S. Priya, K. Ramachandra Rao, P. V. Chalapathi, M. Satyavani, A. Veeraiah, Vibrational and UV spectroscopic studies of 2-coumaranone by experimental and density functional theory calculations, Journal of Molecular Structure, 2017, vol. 1144, pp. 535-544
|
| Hazard Information | Back Directory | [Chemical Properties]
WHITE TO LIGHT YELLOW CRYSTALLINE POWDER | [Uses]
2-Coumaranone has been used to study the effects of coumarins on 7,12-dimethyibenz(a)anthracene induced neoplasia of the rat mammary gland. It was employed as probe for detecting enzymes which hydrolyze 2-hydroxybenzofuran structures. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 47, p. 2491, 1982 DOI: 10.1021/jo00133a055 | [Synthesis]
Preparation of 2-coumarone (I) comprises reacting cyclohexanone (II) with carboxyl-containing acylating agent (III) to methyl 2-(2-oxo-cyclohexyl)-2-hydroxy-acetate (IV) and optional dehydration to a mixture (V) of methyl 2-oxo-cyclohexylidene-acetate and the enol-lactone of the acid; or direct conversion of (I) to (V); and catalytic gas phase dehydrogenation of (IV) or (V) to (I).
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