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