Names | |
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IUPAC name
9H-Fluoren-9-ol
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Other names
9-Hydroxyfluorene
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider |
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ECHA InfoCard | 100.015.345 ![]() |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C13H10O | |
Molar mass | 182.22 g/mol |
Appearance | Off-white crystalline powder |
Density | 1.151 g/mL |
Melting point | 152 to 155 °C (306 to 311 °F; 425 to 428 K) |
Practically insoluble [2] | |
Hazards | |
NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Fluorenol is an alcohol derivative of fluorene. In the most significant isomer, fluoren-9-ol or 9-hydroxyfluorene, the hydroxy group is located on the bridging carbon between the two benzene rings. Hydroxyfluorene can be converted to fluorenone by oxidation. It is a white-cream colored solid at room temperature.
Fluorenol is toxic to aquatic organisms including algae, bacteria, and crustaceans.[3] Fluorenol was patented as an insecticide in 1939,[4] and is an algaecide against the green algae Dunaliella bioculata.[5]
Its toxicity and carcinogenicity in humans are unknown.[5]
A study published by Cephalon describing research to develop a successor to the eugeroic modafinil reported that the corresponding fluorenol derivative was 39% more effective than modafinil at keeping mice awake over a 4-hour period.[6] However, after further investigation it was determined that the eugeroic activity of the fluorenol analog was likely due to an active metabolite, which they identify as fluorenol itself.[6] Fluorenol is a weak dopamine reuptake inhibitor with an IC50 of 9 μM, notably 59% weaker than modafinil (IC50 = 3.70 μM),[6] potentially making it even less liable for addiction.[7] It also showed no affinity for cytochrome P450 2C19, unlike modafinil.[6]
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