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Fluorenone

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 Edit this at Wikidata
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)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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).
checkY verify (what is checkYX markN ?)

Fluorenone is an organic compound with the chemical formula (C6H4)2CO, and is a ketone with a fluorene moiety. It is a bright yellow, fluorescent solid.[2]

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.

Drugs

Fluorenone is used to synthesize:

See also

References

  1. ^ a b c d Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ a b 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 3-527-30673-0.
  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.
  6. ^ Soltani Rad, Mohammad Navid; Behrouz, Somayeh; Zarenezhad, Elham; Moslemin, Mohammad Hossein; Zarenezhad, Ali; Mardkhoshnood, Mehdi; Behrouz, Marzieh; Rostami, Saeid (2 March 2014). "Synthesis of fluorene and/or benzophenone O-oxime ethers containing amino acid residues and study of their cardiovascular and antibacterial effects". Medicinal Chemistry Research. 23 (8): 3810–3822. doi:10.1007/s00044-014-0967-3. ISSN 1054-2523.
  7. ^ Robert B Moffett, US3325544 (1967 to Pharmacia and Upjohn Co).
  8. ^ Allen, Robert E.; Schumann, Edward L.; Day, William C.; Van Campen, M. G. (1958). "Amidines of Certain Substituted Triphenylethylenes". Journal of the American Chemical Society 80 (3): 591–598. doi:10.1021/ja01536a020.
  9. ^ Jr Marcus G Van Campen, Robert E Allen, Frank P Palopoli, Edward L Schumann, US2877269 (1959 to Wm S Merrell Co).
  10. ^ Cookson, R. F.; James, J. W.; Rodway, R. E.; Simmonds, R. G. (1972). "Synthesis of some phenanthridone derivatives". Journal of Heterocyclic Chemistry.9 (3): 475–480. doi:10.1002/jhet.5570090303.
  11. ^ J. W. James and R. E. Rodway, GB1135947 (1968 to Aspro Nicholas Ltd).
  12. ^ Dr Kurt Stach, et al. DE1150976 (1963 to Roche Diagnostics GmbH).
  13. ^ Dr-Ing Kurt Stach, DE1211630 (1966 to Roche Diagnostics GmbH).

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