Chemistry:Fluorenone
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| Names | |
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| Preferred IUPAC name
9H-Fluoren-9-one | |
| Other names
9-Fluorenone; 9-Oxofluorene; Diphenylene ketone
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
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PubChem CID
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| Properties | |
| C13H8O | |
| Molar mass | 180.206 g·mol−1 |
| Appearance | Yellow solid |
| Density | 1.130 g/cm3 (99 °C)[1] |
| Melting point | 84.0 °C (183.2 °F; 357.1 K)[1] |
| Boiling point | 341.5 °C (646.7 °F; 614.6 K)[1] |
| Insoluble | |
| Solubility | soluble in alcohol, acetone, benzene very soluble in ether, toluene |
| log P | 3.58 |
| -99.4·10−6 cm3/mol | |
Refractive index (nD)
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1.6309 |
| Hazards | |
| Main hazards | Irritant |
| Safety data sheet | External MSDS |
| NFPA 704 (fire diamond) | |
| Flash point | 163 °C (325 °F; 436 K)[1] |
| 608 °C (1,126 °F; 881 K) | |
| Related compounds | |
Related compounds
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Fluorene 1,8-Diazafluoren-9-one |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
Tracking categories (test):
Fluorenone is an organic compound with the chemical formula (C
6H
4)
2CO. It is bright fluorescent yellow solid.[2]
Synthesis and reactions
It is synthesised by aerobic oxidation of fluorene:[2]
- (C
6H
4)
2CH
2 + O
2 → (C
6H
4)
2CO + H
2O
Fluorenone sustains up to four nitro groups giving 2,4,5,7-tetranitrofluorenone.[3]
Applications
Several substituted fluorenones are biologically active as antibiotic, anticancer, antiviral, or neuromodulatory compounds.[4]
Some substituted azafluorenones are biologically active, such as the naturally occurring antimicrobial compound onychine (1-methyl-4-azafluorenone).[5] The compound 1,8-diazafluoren-9-one is used for fingerprint detection.
See also
- Fluorenol
- Chlorflurenol
References
- ↑ 1.0 1.1 1.2 1.3 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ↑ 2.0 2.1 Karl Griesbaum; Arno Behr; Dieter Biedenkapp; Heinz-Werner Voges; Dorothea Garbe; Christian Paetz; Gerd Collin; Dieter Mayer et al. (2002). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227. ISBN 3-527-30673-0.
- ↑ Melvin S. Newman and H. Boden (1962). "2,4,5,7-Tetranitrofluorenone". Organic Syntheses 42: 95. doi:10.15227/orgsyn.042.0095.
- ↑ Patel, Sagarkumar; Rathod, Bhagyashri; Regu, Siddulu; Chak, Shivam; Shard, Amit (2020). "A Perspective on Synthesis and Applications of Fluorenones". ChemistrySelect 5 (34): 10673–10691. doi:10.1002/slct.202002695. ISSN 2365-6549.
- ↑ Gomes, Claudia R.B.; de Souza, Marcus V.N.; Facchinetti, Victor (2020-02-24). "A Review on Onychine and its Analogs: Synthesis and Biological Activity". Current Organic Synthesis 17 (1): 3–22. doi:10.2174/1570179417666191218112842. ISSN 1570-1794. PMID 32103713.
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