Fluorenol

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Fluorenol
Names
IUPAC name
9H-Fluoren-9-ol
Other names
9-Fluorenol
9-Hydroxyfluorene
Fluoren-9-ol
Hydrafinil
Properties
C13H10O
Molar mass 182.22 g/mol
Appearance Off-white crystalline powder
Density 1.151 g/cm3[1]
Melting point 152–155 °C (306–311 °F; 425–428 K)
0.043 g/100 ml[2]
Solubility Soluble in acetone, benzene, diethyl ether, tetrahydrofuran
Sparingly soluble in ethanol, hexane, petroleum ether
Hazards
Safety data sheet Sigma-Aldrich
Related compounds
Related compounds
Fluorene
Fluorenone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Fluorenol, 9-fluorenol, also known as hydrafinil, is an organic compound, the alcohol derivative of fluorene.

Properties

Chemical

Fluorenol can be converted to fluorenone by oxidation.

Physical

Fluorenol is a colorless or off-white solid, sparingly soluble in water, but more soluble in other organic solvents.

Availability

Fluorenol is sold by chemical suppliers. It was used as insecticide and may still be commercially available this way.

It is also available as the eugeroic Hydrafinil and can be bought online.

Preparation

Can be prepared by reducing fluorenone using sodium borohydride in tetrahydrofuran.[3]

Other reducing agents that can be used are lithium aluminium hydride[4][5], sodium cyanoborohydride[6], potassium hydroxide + zinc powder[7], though different solvents may be needed, depending on the reducing agent.

Projects

  • Compound collecting
  • Make fluorenone
  • Eugeroic (do NOT consume lab-grade reagents!)

Handling

Safety

Fluorenol does not appear to be toxic to humans or mice. Current research appears to indicate that the compound may act as an eugeroic (promotes mental alertness and wakefulness), similar to modafinil. Fluorenol is a weak dopamine reuptake inhibitor with an IC50 of 9 μM, notably 59% weaker than modafinil (IC50 = 3.70 μM), potentially making it even less liable for addiction. Based on current evidence, its effects in the body can last on average between 6-8 hours, and up to 12 hours.

Fluorenol is known to be toxic to aquatic organisms including algae, bacteria, and crustaceans. It was patented as an insecticide in 1939, and is an algaecide against the green algae Dunaliella bioculata.

Storage

Should be kept in closed bottles, away from light and air.

Disposal

No special disposal is required. Strong UV light and strong oxidizers may be used to break down this compound into harmless products.

References

  1. Banerjee; Zeitschrift fuer Kristallographie, Kristallgeometrie, Kristallphysik, Kristallchemie; vol. 100; (1939); p. 316 - 330
  2. http://www.t3db.ca/toxins/T3D3991
  3. Zeynizadeh, Behzad; Behyar, Tarifeh; Bulletin of the Chemical Society of Japan; vol. 78; nb. 2; (2005); p. 307 - 315
  4. George, Stephen R. D.; Elton, Timothy E.; Harper, Jason B.; Organic and Biomolecular Chemistry; vol. 13; nb. 43; (2015); p. 10745 - 10750
  5. Brown, Eric; Leze, Antoine; Touet, Joel; Tetrahedron Letters; vol. 32; nb. 34; (1991); p. 4309 - 4310
  6. Kouhkan, Mehri; Zeynizadeh, Behzad; Bulletin of the Korean Chemical Society; vol. 31; nb. 10; (2010); p. 2961 - 2966
  7. Handoo, Kishan L.; Gadru, Kanchan; Tetrahedron Letters; vol. 27; nb. 12; (1986); p. 1371 - 1372

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