Fluorene
| Names | |
|---|---|
| IUPAC name
9H-fluorene
| |
| Other names
2,2′-Methylenebiphenyl
2,3-Benzindene Diphenylenemethane o-Biphenylenemethane | |
| Properties | |
| C13H10 (C6H4)2CH2 | |
| Molar mass | 166.223 g/mol |
| Appearance | Colorless solid |
| Density | 1.202 g/cm3 |
| Melting point | 115–117 °C (239–243 °F; 388–390 K) [8] |
| Boiling point | 295 °C (563 °F; 568 K) |
| 0.0000700 g/100 g (0 °C) 0.0001498 g/100 g (20 °C) 0.0001980 g/100 g (25 °C) 0.0003695 g/100 g (40 °C) 0.0006300 g/100 g (50 °C) 0.0008806 g/100 g (60 °C)[1][2] | |
| Solubility | Soluble in benzene, carbon disulfide, diethyl ether, pyridine, toluene, xylene |
| Solubility in acetone | 14.1 g/100 g (20 °C)[3] |
| Solubility in benzene | 25 g/100 g (20 °C) 222 g/100 g (80 °C)[4] |
| Solubility in ethanol | 1.67 g/100 g (10 °C) 2.3 g/100 g (20 °C) 2.9 g/100 g (30 °C) 4.0 g/100 g (40 °C) 5.62 g/100 g (50 °C) 8.53 g/100 g (60 °C) 13.1 g/100 g (70 °C)[5] |
| Solubility in pyridine | 16.61 g/100 g (10 °C) 24.9 g/100 g (20 °C) 34 g/100 g (30 °C) 48 g/100 g (40 °C) 212 g/100 g (80 °C)[6] |
| Solubility in toluene | 20.4 g/100 g (10 °C) 24.13 g/100 g (20 °C) 34.9 g/100 g (30 °C) 49 g/100 g (40 °C) 53.5 g/100 g (50 °C) 97.7 g/100 g (60 °C) 141.5 g/100 g (70 °C) 212.9 g/100 g (80 °C)[7] |
| Vapor pressure | 6.0·10-4 mmHg at 25 °C |
| Acidity (pKa) | 22.6 |
| Thermochemistry | |
| Std enthalpy of
formation (ΔfH |
187.4 kJ/mol[10] |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 152 °C (306 °F; 425 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
16,000 mg/kg (oral, rat) 2 mg/kg (mouse, IP) |
| Related compounds | |
| Related compounds
|
Fluorenol Fluorenone |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Fluorene or 9H-fluorene is an organic chemical compound with the formula (C6H4)2CH2.
Contents
Properties
Chemical
The C9-H sites of the fluorene ring are weakly acidic (pKa = 22.6 in DMSO). Deprotonation gives the stable fluorenyl anion, nominally C13H9-, which is aromatic and has an intense orange color.
Both protons can be removed from C9. For example, 9,9-fluorenyldipotassium can be obtained by treating fluorene with potassium metal in boiling dioxane.
Fluorene and its derivatives can be deprotonated to give ligands akin to cyclopentadienide.
Physical
Fluorene is a colorless crystalline solid, with a distinct aromatic odor, which is insoluble in water, but more soluble in organic solvents, especially aromatics.
Other solubilities for other organic solvents:
- aniline: 10.6 g/100 g (20 °C)
- carbon tetrachloride: 9.1 g/100 g (20 °C)
- chlorobenzene: 20.9 g/100 g (20 °C)
- nitrobenzene: 18.1 g/100 g (20 °C)
- liq. sulfur dioxide: 31.6 g/100 g (20 °C)
- xylene: 19.7 g/100 g (20 °C)
It has a violet fluorescence under UV light, hence its name.
Availability
Fluorene can be obtained from coal tar, although the concentration is low.
It is sold by chemical suppliers and can be bought online.
Preparation
Reduction of fluorenone using various reducing agents, like zinc powder[11], hypophosphorous acid–iodine[12], sodium borohydride[13], or formic acid[14] will yield fluorene.
Fluorene can be obtained from dehydrogenation of diphenylmethane.
Projects
- Make fluorenone and fluorenol
- Make polyfluorene polymers
- Preparation of fluorene dyes
Handling
Safety
Fluorene has been indicated to possess moderate toxicity in animal studies, though there is no clear evidence that it can cause cancer in humans or other animals.
Storage
In closed airtight bottles.
Disposal
Should be neutralized by controlled incineration, in a special burner. Alternatively, oxidizing solutions, which can safely break down aromatics, may be used. Strong UV light in combination with strong oxidizers will also break down this compound.
References
- ↑ Viamajala, Sridhar; Peyton, Brent M.; Richards, Lee A.; Petersen, James N.; Chemosphere; vol. 66; nb. 6; (2007); p. 1094 - 1106,
- ↑ CRC Handbook of Chemistry and Physics. - 90ed. - CRC Press, 2010
- ↑ Solubility Handbook. - T.1, Book.2. - M.-L.: IAN USSR, 1962 (Справочник по растворимости. - Т.1, Кн.2. - М.-Л.: ИАН СССР, 1962)
- ↑ Solubility Handbook. - T.1, Book.2. - M.-L.: IAN USSR, 1962 (Справочник по растворимости. - Т.1, Кн.2. - М.-Л.: ИАН СССР, 1962)
- ↑ Handbook of coke chemistry. - T. 3. - Kharkiv: INJEK, 2009 pp. 362 (Справочник коксохимика. - Т. 3. - Харьков: ИНЖЭК, 2009 pp. 362)
- ↑ Handbook of coke chemistry. - T. 3. - Kharkiv: INJEK, 2009 pp. 362 (Справочник коксохимика. - Т. 3. - Харьков: ИНЖЭК, 2009 pp. 362)
- ↑ Handbook of coke chemistry. - T. 3. - Kharkiv: INJEK, 2009 pp. 362 (Справочник коксохимика. - Т. 3. - Харьков: ИНЖЭК, 2009 pp. 362)
- ↑ Bazyar, Zahra; Hosseini-Sarvari, Mona; Journal of Organic Chemistry; vol. 84; nb. 21; (2019); p. 13503 - 13515
- ↑ Fujita, Hiroaki; Fujimori, Hiroki; Oguni, Masaharu; Journal of Chemical Thermodynamics; vol. 27; nb. 8; (1995); p. 927 - 938
- ↑ Orlov; Turovtsev; Lebedev; Russian Chemical Bulletin; vol. 50; nb. 9; (2001); p. 1570 - 1571
- ↑ Fittig, Rud. (1873), "Ueber einen neuen Kohlenwasserstoff aus dem Diphenylenketon" Ber. Dtsch. Chem. Ges. volume 6, p. 187
- ↑ Hicks, Latorya D.; Han, Ja Kyung; Fry, Albert J. (2000). "Hypophosphorous acid–iodine: a novel reducing system". Tetrahedron Letters. Elsevier BV. 41 (41): 7817–7820
- ↑ Ono, Aoi; Suzuki, Nobuko; Kamimura, Junko; Synthesis; nb. 8; (1987); p. 736 - 738
- ↑ Singh, Ajay K.; Jang, Seungwook; Kim, Jae Yul; Sharma, Siddharth; Basavaraju; Kim, Min-Gyu; Kim, Kyung-Rok; Lee, Jae Sung; Lee, Hong H.; Kim, Dong-Pyo; ACS Catalysis; vol. 5; nb. 11; (2015); p. 6964 - 6972
