Fluorenol

Fluorenol[1]
Names
IUPAC name
9H-Fluoren-9-ol
Other names
9-Hydroxyfluorene
Identifiers
1689-64-1 YesY
ChEBI CHEBI:16904 N
ChemSpider 66916 N
EC Number 216-879-0
Jmol interactive 3D Image
PubChem 74318
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
Flammability code 0: Will not burn. E.g., water Health code 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g., sodium chloride Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
0
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

Toxicity

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]

Wakefulness-promoting agent

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, which is structurally related, was 39% more effective than modafinil at keeping mice awake over a 4-hour period.[6] 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.[7] It also showed no affinity for cytochrome P450 2C19, unlike modafinil.[6]

See also

References

  1. ↑ 9-Hydroxyfluorene, chemicalland21.com
  2. ↑ Record of 9H-Fluoren-9-ol in the GESTIS Substance Database of the IFA, accessed on 5 November 2008
  3. ↑ Šepič, Ester; Bricelj, Mihael; Leskovšek, Hermina (2003). "Toxicity of fluoranthene and its biodegradation metabolites to aquatic organisms". Chemosphere 52 (7): 1125–33. doi:10.1016/S0045-6535(03)00321-7. PMID 12820993.
  4. ↑ US patent 2197249: Insecticide
  5. 1 2 MSDS
  6. 1 2 Dunn, D.; Hostetler, G.; Iqbal, M.; Marcy, V. R.; Lin, Y. G.; Jones, B.; Aimone, L. D.; Gruner, J.; Ator, M. A.; Bacon, E. R.; Chatterjee, S. (2012). "Wake promoting agents: Search for next generation modafinil, lessons learned: Part III". Bioorganic & Medicinal Chemistry Letters 22 (11): 3751–3753. doi:10.1016/j.bmcl.2012.04.031. PMID 22546675.
  7. ↑ Wise, R. A. (1996). "Neurobiology of addiction". Current Opinion in Neurobiology 6 (2): 243–51. doi:10.1016/S0959-4388(96)80079-1. PMID 8725967.

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