Fluorenone

Not to be confused with Fluorone, Fluorene, or Fluorine.

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

Fluorenone

Names
Preferred IUPAC name 9H-Fluoren-9-one
Other names 9-Fluorenone; 9-Oxofluorene; Diphenylene ketone
Identifiers
CAS Number	486-25-9 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17922 Y
ChEMBL	ChEMBL571655 Y
ChemSpider	9824 Y
ECHA InfoCard	100.006.937
KEGG	C06712 Y
PubChem CID	10241
UNII	AZ9T83S2AQ Y
CompTox Dashboard (EPA)	DTXSID6049307
InChI 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
SMILES c1ccc2c(c1)-c3ccccc3C2=O
Properties
Chemical formula	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]
Solubility in water	Insoluble
Solubility	soluble in alcohol, acetone, benzene very soluble in ether, toluene
log P	3.58
Magnetic susceptibility (χ)	−99.4·10−6 cm3/mol
Refractive index (nD)	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]
Autoignition temperature	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

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

• Fluorenol
• Chlorflurenol