{{distinguish|Fluorone|Fluorene|Fluorine}} {{chembox | Watchedfields = changed | verifiedrevid = 443822969 | Name = | ImageFile = Fluorenone-skeletal.svg | ImageClass = skin-invert-image | ImageSize = 160px | ImageAlt = Skeletal formula of fluorenone | ImageFile1 = Fluorenone molecule ball.png | ImageClass1 = bg-transparent | ImageAlt1 = Ball-and-stick model of the fluorenone molecule | PIN = 9''H''-Fluoren-9-one | OtherNames = 9-Fluorenone; 9-Oxofluorene; Diphenylene ketone | Section1 = {{Chembox Identifiers | Abbreviations = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 9824 | InChIKey = YLQWCDOCJODRMT-UHFFFAOYAR | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 571655 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C13H8O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8H | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = YLQWCDOCJODRMT-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 486-25-9 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = AZ9T83S2AQ | EINECS = | PubChem = 10241 | SMILES = c1ccc2c(c1)-c3ccccc3C2=O | InChI = 1/C13H8O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8H | RTECS = | MeSHName = | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 17922 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C06712 }} | Section2 = {{Chembox Properties | C=13 | H=8 | O=1 | Appearance = Yellow solid | Density = 1.130 g/cm<sup>3</sup> (99 °C)<ref name=GESTIS>{{GESTIS|ZVG=35750}}</ref> | MeltingPtC = 84.0 | MeltingPt_ref = <ref name=GESTIS/> | BoilingPtC = 341.5 | BoilingPt_ref = <ref name=GESTIS/> | Solubility = Insoluble | SolubleOther = soluble in alcohol, acetone, benzene <br /> very soluble in ether, toluene | RefractIndex = 1.6309 | pKa = | pKb = | MagSus = −99.4·10<sup>−6</sup> cm<sup>3</sup>/mol | LogP = 3.58 }} | Section5 = {{Chembox Hazards | ExternalSDS = [http://physchem.ox.ac.uk/MSDS/FL/9-fluorenone.html External MSDS] | MainHazards = Irritant | NFPA-H = 1 | NFPA-F = 1 | NFPA-R = 0 | NFPA-S = | FlashPtC = 163 | FlashPt_ref = <ref name=GESTIS/> | AutoignitionPtC = 608 | ExploLimits = | PEL = }} | Section6 = {{Chembox Related | OtherAnions = | OtherCations = | OtherFunction = | OtherFunction_label = | OtherCompounds = Fluorene<br />1,8-Diazafluoren-9-one}} }}
'''Fluorenone''' is an organic compound with the chemical formula {{chem2|(C6H4)2CO}}, and is a ketone with a fluorene moiety. It is a bright yellow, fluorescent solid.<ref name=Ullmanns/>
==Synthesis and reactions== It is synthesised by aerobic oxidation of fluorene:<ref name=Ullmanns>{{cite encyclopedia |author=Karl Griesbaum |author2=Arno Behr |author3=Dieter Biedenkapp |author4=Heinz-Werner Voges |author5=Dorothea Garbe |author6=Christian Paetz |author7=Gerd Collin |author8=Dieter Mayer |author9=Hartmut Höke |title=Hydrocarbons|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2002|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a13_227|isbn=3-527-30673-0}}</ref> :{{chem2|(C6H4)2CH2 + O2 -> (C6H4)2CO + H2O}}
Fluorenone sustains up to four nitro groups giving 2,4,5,7-tetranitrofluorenone.<ref>{{cite journal |doi=10.15227/orgsyn.042.0095|title=2,4,5,7-Tetranitrofluorenone |journal=Organic Syntheses |year=1962 |volume=42 |page=95|author=Melvin S. Newman and H. Boden }}</ref>
==Applications==
Several substituted '''fluorenones''' are biologically active as antibiotic, anticancer, antiviral, or neuromodulatory compounds.<ref name="Patel 2020">{{cite journal | last1=Patel | first1=Sagarkumar | last2=Rathod | first2=Bhagyashri | last3=Regu | first3=Siddulu | last4=Chak | first4=Shivam | last5=Shard | first5=Amit | title=A Perspective on Synthesis and Applications of Fluorenones | journal=ChemistrySelect | volume=5 | issue=34 | date=2020 | issn=2365-6549 | doi=10.1002/slct.202002695 | pages=10673–10691| s2cid=224995927 }}</ref>
Some substituted '''azafluorenones''' are biologically active, such as the naturally occurring antimicrobial compound onychine (1-methyl-4-azafluorenone).<ref name="Gomes 2020">{{cite journal | last1=Gomes | first1=Claudia R.B. | last2=de Souza | first2=Marcus V.N. | last3=Facchinetti | first3=Victor | title=A Review on Onychine and its Analogs: Synthesis and Biological Activity | journal=Current Organic Synthesis | volume=17 | issue=1 | date=2020-02-24 | issn=1570-1794 | doi=10.2174/1570179417666191218112842 | pages=3–22| pmid=32103713 | s2cid=211535420 }}</ref> 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].<ref>{{Cite journal |last=Soltani Rad |first=Mohammad Navid |last2=Behrouz |first2=Somayeh |last3=Zarenezhad |first3=Elham |last4=Moslemin |first4=Mohammad Hossein |last5=Zarenezhad |first5=Ali |last6=Mardkhoshnood |first6=Mehdi |last7=Behrouz |first7=Marzieh |last8=Rostami |first8=Saeid |date=2 March 2014 |title=Synthesis of fluorene and/or benzophenone O-oxime ethers containing amino acid residues and study of their cardiovascular and antibacterial effects |url=http://link.springer.com/10.1007/s00044-014-0967-3 |journal=Medicinal Chemistry Research |language=en |volume=23 |issue=8 |pages=3810–3822 |doi=10.1007/s00044-014-0967-3 |issn=1054-2523|url-access=subscription }}</ref> *An analog of 2-MDP.<ref>Robert B Moffett, US3325544 (1967 to Pharmacia and Upjohn Co).</ref> *Paranyline (aka Renytoline, Mer 27).<ref>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.</ref><ref>Jr Marcus G Van Campen, Robert E Allen,Frank P Palopoli, Edward L Schumann, US2877269 (1959 to Wm S Merrell Co).</ref> *Via a Beckmann rearrangement, phenanthridone [1015-89-0]. This compound is used in the synthesis of fantridone.<ref>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.</ref><ref>J. W. James and R. E. Rodway, GB1135947 (1968 to Aspro Nicholas Ltd).</ref> *An analog of amitriptyline, as reported by Roche: [4684-13-3].<ref>Dr Kurt Stach, et al. DE1150976 (1963 to Roche Diagnostics GmbH).</ref><ref>Dr-Ing Kurt Stach, DE1211630 (1966 to Roche Diagnostics GmbH).</ref>
==See also== * Fluorenol * Chlorflurenol
==References== {{reflist}}
==External links== *[https://fscimage.fishersci.com/msds/48562.htm Material Safety Data Sheet] {{Webarchive|url=https://web.archive.org/web/20120228200118/https://fscimage.fishersci.com/msds/48562.htm |date=2012-02-28 }}
Category:Fluorenones Category:Designer drugs