Fluorenone

Fluorenone is an aromatic organic compound with the chemical formula C13H8O. It is bright fluorescent yellow in color and is a solid at room temperature.

Not to be confused with Fluorone, Fluorene, or Fluorine.
Fluorenone
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 Y
    Key: YLQWCDOCJODRMT-UHFFFAOYSA-N Y
  • 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).
Y verify (what is YN ?)
Infobox references

It can be synthesised from fluorene with the addition of glacial acetic acid and sodium hypochlorite solution, undergoing an oxidation reaction.

Several substituted fluorenones are biologically active as antibiotic, anticancer, antiviral, or neuromodulatory compounds.[2]

Some substituted azafluorenones are biologically active, such as the naturally occurring antimicrobial compound onychine (1-methyl-4-azafluorenone).[3] The compound 1,8-diazafluoren-9-one is used for fingerprint detection.

Medicine uses

Fluorenone has uses in medicinal chemistry, for example in the synthesis of Paranyline, IPS-339 [60979-28-4], Fanthridone, & SKF 550 [38776-87-3] among others.

A pair of patents was disclosed for an analog of amitriptyline that relies on fluorenone starting material [4684-13-3].[4][5]

See also

References
  1. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 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.
  3. 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.
  4. Dr-Ing Kurt Stach, DE1211630 (1966 to Roche Diagnostics GmbH).
  5. Dr Kurt Stach, et al. DE1150976 (1963 to Roche Diagnostics GmbH).
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