Fluorenol

Fluorenol
Names


IUPAC name 9H-Fluoren-9-ol
Other names 9-Hydroxyfluorene
Identifiers
CAS Number	1689-64-1^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16904^N
ChemSpider	66916^N
ECHA InfoCard	100.015.345
EC Number	216-879-0
PubChem	74318
InChI InChI=1S/C13H10O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8,13-14H^N Key: AFMVESZOYKHDBJ-UHFFFAOYSA-N^N InChI=1/C13H10O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8,13-14H Key: AFMVESZOYKHDBJ-UHFFFAOYAM
SMILES C1=CC=C2C(=C1)C(C3=CC=CC=C32)O
Properties
Chemical formula	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)
Solubility in water	Practically insoluble
Hazards
NFPA 704	0 0 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

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. Fluorenol was patented as an insecticide in 1939, and is an algaecide against the green algae Dunaliella bioculata.

Its toxicity and carcinogenicity in humans are unknown.

A study published by chemists working for the biopharmaceutical company Cephalon to develop a successor to the wakefulness-promoting agent (or eugeroic) modafinil reported that fluorenol was 39% more effective than modafinil at keeping mice awake over a 4-hour period. It is a weak dopamine reuptake inhibitor with an IC₅₀ of 9 μM, notably 59% weaker than modafinil (IC₅₀ = 3.70 μM) despite being a stronger wakefulness-promoting agent, potentially making it even less liable for addiction. It also showed no affinity for cytochrome P450 2C19, unlike modafinil.

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