Fluorene

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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
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):
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.

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:

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 acidiodine[12], sodium borohydride[13], or formic acid[14] will yield fluorene.

Fluorene can be obtained from dehydrogenation of diphenylmethane.

Projects

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

  1. Viamajala, Sridhar; Peyton, Brent M.; Richards, Lee A.; Petersen, James N.; Chemosphere; vol. 66; nb. 6; (2007); p. 1094 - 1106,
  2. CRC Handbook of Chemistry and Physics. - 90ed. - CRC Press, 2010
  3. Solubility Handbook. - T.1, Book.2. - M.-L.: IAN USSR, 1962 (Справочник по растворимости. - Т.1, Кн.2. - М.-Л.: ИАН СССР, 1962)
  4. Solubility Handbook. - T.1, Book.2. - M.-L.: IAN USSR, 1962 (Справочник по растворимости. - Т.1, Кн.2. - М.-Л.: ИАН СССР, 1962)
  5. Handbook of coke chemistry. - T. 3. - Kharkiv: INJEK, 2009 pp. 362 (Справочник коксохимика. - Т. 3. - Харьков: ИНЖЭК, 2009 pp. 362)
  6. Handbook of coke chemistry. - T. 3. - Kharkiv: INJEK, 2009 pp. 362 (Справочник коксохимика. - Т. 3. - Харьков: ИНЖЭК, 2009 pp. 362)
  7. Handbook of coke chemistry. - T. 3. - Kharkiv: INJEK, 2009 pp. 362 (Справочник коксохимика. - Т. 3. - Харьков: ИНЖЭК, 2009 pp. 362)
  8. Bazyar, Zahra; Hosseini-Sarvari, Mona; Journal of Organic Chemistry; vol. 84; nb. 21; (2019); p. 13503 - 13515
  9. Fujita, Hiroaki; Fujimori, Hiroki; Oguni, Masaharu; Journal of Chemical Thermodynamics; vol. 27; nb. 8; (1995); p. 927 - 938
  10. Orlov; Turovtsev; Lebedev; Russian Chemical Bulletin; vol. 50; nb. 9; (2001); p. 1570 - 1571
  11. Fittig, Rud. (1873), "Ueber einen neuen Kohlenwasserstoff aus dem Diphenylenketon" Ber. Dtsch. Chem. Ges. volume 6, p. 187
  12. 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
  13. Ono, Aoi; Suzuki, Nobuko; Kamimura, Junko; Synthesis; nb. 8; (1987); p. 736 - 738
  14. 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

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