Fluorenone

Chemical compound From Wikipedia, the free encyclopedia

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

Quick facts Names, Identifiers ...
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).
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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 in the synthesis of a drug that is called IPS-339 [60979-28-4].
  • The synthesis of an analog of 2-MDP:[6]
  • Paranyline (aka Renytoline, Mer 27).[7][8]
  • Beckmann rearrangement of Fluorenone leads to phenanthridone [1015-89-0]. This compound in-turn is used in the synthesis of Fanthridone.[9][10]
  • Roche reported an analog of amitriptyline: [4684-13-3].[11][12]

See also

References

External links

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