Fluorenol

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Fluorenol[1]
Fluorenol.png
9-fluorenol.png
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 3D model Interactive image
PubChem 74318
  • 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
  • C1=CC=C2C(=C1)C(C3=CC=CC=C32)O
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]
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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

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  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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ US patent 2197249: Insecticide
  5. ↑ 5.0 5.1 MSDS
  6. ↑ 6.0 6.1 Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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