Fluorenone

Fluorenone
Names
	Preferred IUPAC name 9H-Fluoren-9-one
	Other names 9-Fluorenone; 9-Oxofluorene; Diphenylene ketone
Identifiers
CAS Number	486-25-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17922 ;
ChEMBL	ChEMBL571655 ;
ChemSpider	9824 ;
ECHA InfoCard	100.006.937
KEGG	C06712 ;
PubChem CID	10241;
UNII	AZ9T83S2AQ ;
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 Key: YLQWCDOCJODRMT-UHFFFAOYSA-N ; 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)
Melting point	84.0 °C (183.2 °F; 357.1 K)
Boiling point	341.5 °C (646.7 °F; 614.6 K)
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)
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). verify (what is ?) Infobox references

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:

A drug called IPS-339 [60979-28-4].^[6]
An analog of 2-MDP.^[7]
Paranyline (aka Renytoline, Mer 27).^[8]^[9]
Via a Beckmann rearrangement, phenanthridone [1015-89-0]. This compound is used in the synthesis of fantridone.^[10]^[11]
An analog of amitriptyline, as reported by Roche: [4684-13-3].^[12]^[13]

References

1 2 3 4 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
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.
↑ Melvin S. Newman and H. Boden (1962). "2,4,5,7-Tetranitrofluorenone". Organic Syntheses. 42: 95. doi:10.15227/orgsyn.042.0095.
↑ 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.
↑ 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.
↑ 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.
↑ Robert B Moffett, US3325544 (1967 to Pharmacia and Upjohn Co).
↑ 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.
↑ Jr Marcus G Van Campen, Robert E Allen,Frank P Palopoli, Edward L Schumann, US2877269 (1959 to Wm S Merrell Co).
↑ 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.
↑ J. W. James and R. E. Rodway, GB1135947 (1968 to Aspro Nicholas Ltd).
↑ Dr Kurt Stach, et al. DE1150976 (1963 to Roche Diagnostics GmbH).
↑ Dr-Ing Kurt Stach, DE1211630 (1966 to Roche Diagnostics GmbH).

External links

Material Safety Data Sheet Archived 2012-02-28 at the Wayback Machine

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

[Ullmanns-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.

[Patel_2020-4] 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.

[Gomes_2020-5] 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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