Fluorenone

Last updated
Fluorenone
Fluorenone-skeletal.svg
Fluorenone molecule ball.png
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C13H8O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8H Yes check.svgY
    Key: YLQWCDOCJODRMT-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceYellow 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.svgHealth 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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

Contents

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. 1 2 3 4 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 1 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   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.
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