Fluorenone

Fluorenone is an organic compound with the chemical formula (C6H4)2CO. It is bright fluorescent yellow solid.[2]

Not to be confused with Fluorone, Fluorene, or Fluorine.
Fluorenone
Skeletal formula of fluorenone
Ball-and-stick model of the fluorenone molecule
Names
Preferred IUPAC name
9H-Fluoren-9-one
Other names
9-Fluorenone; 9-Oxofluorene; Diphenylene ketone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.937
KEGG
UNII
  • InChI=1S/C13H8O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8H checkY
    Key: YLQWCDOCJODRMT-UHFFFAOYSA-N checkY
  • InChI=1/C13H8O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8H
    Key: YLQWCDOCJODRMT-UHFFFAOYAR
  • c1ccc2c(c1)-c3ccccc3C2=O
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
1.6309
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant
NFPA 704 (fire diamond)
1
1
0
Flash point 163 °C (325 °F; 436 K)[1]
608 °C (1,126 °F; 881 K)
Safety data sheet (SDS) External MSDS
Related compounds
Related compounds
 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).
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Infobox references

Synthesis and reactions

It is synthesised by aerobic oxidation of fluorene:[2]

(C6H4)2CH2 + O2 → (C6H4)2CO + H2O

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

References
  1. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. Karl Griesbaum, Arno Behr, Dieter Biedenkapp, Heinz-Werner Voges, Dorothea Garbe, Christian Paetz, Gerd Collin, Dieter Mayer, Hartmut Höke (2002). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227. ISBN 3527306730.{{cite encyclopedia}}: CS1 maint: uses authors parameter (link)
  3. Melvin S. Newman and H. Boden (1962). "2,4,5,7-Tetranitrofluorenone". Organic Syntheses. 42: 95. doi:10.15227/orgsyn.042.0095.
  4. 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. S2CID 224995927.
  5. 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. S2CID 211535420.
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