1,3-Diphenylisobenzofuran

Chemistry Lots of missing key reagents in images and incorrect/confusing (possibly "non-chemist translation engine"?) chemical terminology September 2019 File:1,3-Diphenylisobenzofuran Struktur.svg 130px skin-invert 1,3-Diphenylisobenzofuran sample.jpg 1,3-Diphenyl-2-benzofuran 5471-63-6 correct CAS correct FDA OQ2CY31MDT 20348 226-808-5 21649 1S/C20H14O/c1-3-9-15(10-4-1)19-17-13-7-8-14-18(17)20(21-19)16-11-5-2-6-12-16/h1-14H ZKSVYBRJSMBDMV-UHFFFAOYSA-N C1=CC=C(C=C1)C2=C3C=CC=CC3=C(O2)C4=CC=CC=C4 20 14 1 pale yellowhttp://www.tcichemicals.com/eshop/de/de/commodity/D1520 1,3-Diphenylisobenzofuran 5471-63-6 TCI Deutschland GmbH www.tcichemicals.com de 2018-01-14 to dark yellow crystalline powderAldrich 105481 1,3-Diphenylisobenzofuran 97% 27. Juli 2017 1.0717 g·cm−3 bei 25 °CCarl L. Yaws Thermophysical Properties of Chemicals and Hydrocarbons, 2nd Edition Elsevier Inc. Oxford, UK 604 978-0-323-28659-6 2015 * 125–126 °C 128–130 °C almost insoluble solubleP.C. Kierkus E-EROS Encyclopedia of Reagents for Organic Synthesis 1,3-Diphenylisobenzofuran 2001 10.1002/047084289X.rd420 0471936235 acetonitrile, benzene, dichloromethane, chloroform, dimethylsulfoxide, tetrahydrofuran or toluene 1,3-Diphenylisobenzofuran is a highly reactive diene that can scavenge unstable and short-lived dienophiles in a Diels-Alder reaction. It is furthermore used as a standard reagentR.H. Young K. Wehrly R.L. Martin Journal of the American Chemical Society Solvent effects in dye-sensitized photooxidation reactions 93 22 5774–5779 1971 10.1021/ja00751a031 1971JAChS..93.5774Y for the determination of singlet oxygen,J.A. Howard G.D. Mendenhall Canadian Journal of Chemistry Autoxidation and photooxidation of 1,3-diphenylisobenzofuran: A kinetic and product study 53 14 2199–2201 1975 10.1139/v75-307 even in biological systems.P. Carloni etal Res. Chem. Intermed. On the use of 1,3-diphenylisobenzofuran (DPBF). Reactions with carbon and oxygen centered radicals in model and natural systems 19 5 395–405 1993 10.1163/156856793X00181 94802096 Cycloadditions with 1,3-diphenylisobenzofuran and subsequent oxygen cleavage provide access to a variety of polyaromatics. Preparation The first synthesis of 1,3-diphenylisobenzofuran was reported in 1905 by A. Guyot and J. Catel.A. Guyot, J. Catel, Bull. Soc. Chim. France, [3] (35), 1124 (1906)A. Guyot, J. Catel, Compt. Rend. Hebd. Acad. Sci., Ser. C140, 1348 (1905) Phenylmagnesium bromide was reacted with 3-phenylphthalide (the latter accessible from the methyl ester of 3-hydroxyphthalide with phenylboronic acid in 95% yieldM. Kuriyama N. Ishiyama R. Shimazawa R. Shirai O. Onomura Journal of Organic Chemistry Efficient synthesis of 3-arylphthalides using palladium-catalyzed arylation of aldehydes with organoboronic acids 74 23 9210–9213 2009 10.1021/jo901964k 19873994 ) to a lactol, which dehydrates to 1,3-diphenylisobenzofuran with 87% yield. A mineral acid catalyzes the dehydration reaction.M. S. Newman Journal of Organic Chemistry Evidence favoring a two-step mechanism for the Diels-Alder reaction 26 8 2630–2633 1961 10.1021/jo01066a004 400px|center|Synthese von 1,3-Diphenylisobenzofuran aus 3-Phenylphthalid The patent literature describes the preparation of 1,3-diphenylisobenzofuran by [4+2]cycloaddition of 1,3-butadiene and dibenzoylethylene (1,4-diphenyl-2-butene-1,4-dione, accessible from fumaryl chloride and benzene in the presence of aluminium chloride.CV3P0248 R.E. Lutz trans-Dibenzoylethylene 1940 20 29 3 248 10.15227/orgsyn.020.0029). US 2325727 Dehydroisobenzofurans and process for preparing them 1943-08-03 1940-07-27 R. Adams E.I. du Pont de Nemours & Co. Dibenzoylethylene is predominantly present in the trans configurationhttps://www.thermofisher.com/order/catalog/product/L12643.03?SID=srch-srp-L12643.06 1,2-Dibenzoylethylene, predominantly trans, 96% Thermo Scientific Chemicals but it can be converted into the needed cis configuration by simple heating.D.V. Klemm A. Tuncay J. Chem. Educ. Photochemical and thermal isomerization of trans- and cis-1,2-dibenzoylethylene: A microscale approach 66 6 519 1989 10.1021/ed066p519 1989JChEd..66..519K 400px|center|Synthese von 1,3-Diphenylisobenzofuran aus Butadien und Dibenzoylethylen The 4,5-dibenzoylcyclohexene formed previously is cyclized with acetic anhydride to the dihydroisobenzofuran. By bromine addition and hydrogen bromide elimination, 1,2-dibenzoylbenzene is formed and recyclized with zinc acetic acid to the final product 1,3-diphenylisobenzofuran. US 2356907 1,3-Diphenylisobenzofurans and process for preparing the same 1944-08-29 1940-07-27 R. Adams E.I. du Pont de Nemours & Co. A publication from 1940 describes high yields for the individual stages of the extensive reaction sequence.R. Adams M.H. Gold Journal of the American Chemical Society The Synthesis of 1,3-Diphenyldihydroisobenzofurans, 1,3-Diphenylisobenzofurans and o-Dibenzoylbenzenes from the Diene Addition Products to Dibenzoylethylene 62 1 56–61 1940 10.1021/ja01858a012 1940JAChS..62...56A The (much cheaper) phthaloyl chloride gives also access to 1,2-dibenzoylbenzene via Friedel-Crafts acylation with benzene,Houben-Weyl Methods of Organic Chemistry XIII/2a Organometallic Compounds of Group II of the Periodic Table, 4th Edition Thieme Stuttgart 419 978-3-13-213204-7 1973 which is reduced to 1,3-diphenylisobenzofuran in 78% yield using potassium borohydride.M. Cava M.J. Mitchell A.A. Deana Journal of Organic Chemistry Condensed cyclobutane aromatic compounds. XIII. An attempted synthesis of 1,2-diphenylbenzocyclobutene 25 9 1481–1484 1960 10.1021/jo01079a005 500px|center|Synthese von 1,3-Diphenylisobenzofuran aus 1,2-Dibenzoylbenzol The synthesis of 1,3-diarylisobenzofurans from 2-acylbenzaldehydes and boronic acids is less cumbersome and gives better yields,J. Jacq B. Bessières C. Einhorn J. Einhorn Org. Biomol. Chem. Regiospecific synthesis of functionalised 1,3-diarylisobenzofurans via palladium- and rhodium-catalysed reaction of boronic acids with o-acylbenzaldehydes under thermal or microwave activation 8 4927–4933 2010 21 10.1039/c0ob00110d 20740250 450px|center|Synthese von 1,3-Diphenylisobenzofuran aus 2-Formylbenzophenon just like the synthesis from salicylaldehydes via phenacylhydrazones, which undergo oxidation with lead(IV) acetate to give ortho-diketones,A. Kotali P.G. Tsoungas Tetrahedron Lett. Oxidation of N-aroylhydrazones of o-hydroxyaryl ketones with lead(IV)acetate: A facile route to aromatic o-diketones 28 37 4321–4322 1987 10.1016/S0040-4039(00)96497-9 followed by the reaction with an aryl Grignard reagent.J. Jacq C. Einhorn J. Einhorn Org. Lett. A versatile and regiospecific synthesis of functionalised 1,3-diarylisobenzofurans 10 17 3757–3760 2008 10.1021/ol801550a 18666776 450px|center|Synthese von 1,3-Diphenylisobenzofuran aus Salicylaldehyd Properties 1,3-Diphenylisobenzofuran is a yellow, light- and air-sensitive, crystalline solid that is soluble in many organic solvents with a maximum absorption around 420 nm (in solution), which generates intense fluorescence.M. Wozniak F. Tanfani E. Bertoli G. Zolese J. Antonsiewicz Biochim. Biophys. Acta A new fluorescence method to detect singlet oxygen inside phospholipid model membranes 1082 1 94–100 1991 10.1016/0005-2760(91)90304-Z 1849016 Fluorescence measurements can be performed in DMF and DMSO because of the stability of 1,3-DPBF in those solvents. In chloroform and carbon tetrachloride the dissolved 1,3-diphenylisobenzofuran is rapidly photolyzed by attack of CHCl2 and CCl3 radicals, even in the absence of oxygen.X.-F. Zhang X. Liu Journal of Luminiscence The photostability and fluorescence properties of diphenylisobenzofuran 131 11 2263–2266 2011 10.1016/j.jlumin.2011.05.048 2011JLum..131.2263Z [24 ] With ethanol, 1,3-diphenylisobenzofuran forms an orange-yellow, fluorescent solution. On irradiation, it forms a colorless photodimer (upon with exclusion of oxygen), upon discolouration of the solution.A. Schönberg A. Mustafa G. Aziz Journal of the American Chemical Society Diels-Alder Reaction. II. Experiments with 2-Styrylchromones. On the Nature of the Dimer of 1,3-Diphenylisobenzofuran 76 18 4576–4577 September 1, 1954 10.1021/ja01647a020 1954JAChS..76.4576S 350px|center|Photodimerisierung von 1,3-Diphenylisobenzofuran The compound's refractive index is 1,6700 at 25 °C and 589 nm. Use Reagent for determination of singlet oxygen 500px|center|1,3-Diphenylisobenzofuran Reaktion mit Singulett-Sauerstoff thumb|Graph showing change in absorbance of DPBF vs. irradiation time in the presence of photosensitizer (porphyrin)Axial ligand modified high valent tin(iv) porphyrins: synthesis, structure, photophysical studies and photodynamic antimicrobial activities on Candida albicans RSC Adv. 30 Jun 2015 5 61103 10.1039/C5RA09343K https://pubs.rsc.org/en/content/articlelanding/2015/ra/c5ra09343k Soman Rahul Raghav Darpan Sujatha Subramaniam Rathinasamy Krishnan Arunkumar Chellaiah 75 2015RSCAd...561103S subscription thumb|Electron absorption spectrum showing photodegradation of DPBF in the presence of a porphyrin photosensitzier, during intermittent periods of irradiation with ~630 nm light In the presence of methylene blue irradiated with red laser light, 1,3-diphenylisobenzofuran reacts with intermediate singlet oxygen 1O2, forming an unstable peroxide that decomposes into (colorless) 1,2-dibenzoylbenzene.Grundpraktikum Physikalische Chemie, V28, Photooxidation von Diphenylisobenzofuran, Untersuchung der Reaktionskinetik durch Photometrie Universität Ulm https://www.uni-ulm.de/physchem-praktikum/media/ap/v_28.pdf 2017-08-30 https://web.archive.org/web/20170517015145/http://www.uni-ulm.de/physchem-praktikum/media/ap/v_28.pdf 2017-05-17 2010-12-06 German dead The detection of singlet oxygen by 1,3-diphenylisobenzofuran is based on this reaction, even in biological systems. For biological systems, water-soluble derivatives of 1,3-diphenylisobenzofuran were developed.C. Schmitz J.M. Aubry J. Rigaudy Tetrahedron A new access to the anthracene core: Synthesis of two water soluble singlet oxygen traps derived from 1,3-diphenylisobenzofuran and 9,10-diphenylanthracene 38 10 1425–1430 1982 10.1016/0040-4020(82)80224-X The singlet oxygen generation of photosensitizers were monitored by photolysis of 1,3-diphenylisobenzofuran (DPBF). 1,2-Dibenzoylbenzene absorbs at <300 nm, therefore making DPBF an optimal chemical trap for detecting singlet oxygen, as most photosensitizers absorb <400-600 nm. This allows for an accurate determination of the photodegradation of the molecule. Dienophile in Diels-Alder reactions Isobenzofurans like 1,3-diphenylisobenzofuran are among the most reactive Diels-Alder dienes known to date,D. Tobia B. Rickborn Journal of Organic Chemistry Substituent effects on rates of inter- and intramolecular cycloaddition reactions of isobenzofurans 52 12 2611–2615 1987 10.1021/jo00388a055 and are useful for scavenging short-lived and unstable olefins and alkynes. The group led by Georg Wittig made important contributions to this topic. With the unstable cyclohexyne, 1,3-diphenylisobenzofuran reacts to a tricyclic compound that gives a 9,10-diphenylcyclohexenonaphthalene after hydrogenation and hydrogen abstraction.G. Wittig Pure Appl. Chem. Über kleine Ringe mit Kohlenstoffdreifachbindung – noch eine Chemie des "Als ob" 7 2–3 173–192 1963 German 10.1351/pac196307020173 1963PApCh...7..173W 95499778 500px|center|Reaktion von 1,3-Diphenylisobenzofuran mit Cyclohexin 1,3-Diphenylisobenzofuran gives similarly with benzyne (dehydrobenzene) an oxygen-bridged anthracene (in 85% yield), which can be reduced with zinc to 9,10-diphenylanthracene (88% yield).G. Wittig E. Knauss K. Niethamer Justus Liebigs Ann. Chem. Über 9,10-Dihydroanthracen-Derivate mit Heterobrückenatomen 630 1 10–18 1960 German 10.1002/jlac.19606300103 500px|center|Reaktion von 1,3-Diphenylisobenzofuran mit Dehydrobenzol Cyclopropenone (which is unstable above its melting point of −29 °C) reacts quantitatively at room temperature with 1,3-diphenylisobenzofuran to form a Diels-Alder adduct,R. Breslow M. Oda Journal of the American Chemical Society Isolation and characterization of pure cyclopropenone 94 13 4787–4788 1972 10.1021/ja00768a089 1972JAChS..94.4787B which is exclusively an exo isomer.Exo selectivity of the Diels-Alder addition of cyclopropenone and 1-3-diphenylisobenzofuran http://www.ch.ic.ac.uk/motm/porphyrins/P2.html 2017-08-28 400px|center|Reaktion von 1,3-Diphenylisobenzofuran mit Cyclopropenon Dimethyl acetylenedicarboxylate reacts with 1,3-diphenylisobenzofuran as dienophile in 84% yield to yield the corresponding adduct.J.A. Berson Journal of the American Chemical Society Reactions of 1,3-diphenylisobenzofuran with acetylenic dienophiles 75 5 1240–1241 1953 10.1021/ja01101a503 1953JAChS..75.1240B 400px|center|Reaktion von 1,3-Diphenylisobenzofuran mit Acetylendicarbonsäureester 1,3-Diphenylisobenzofuran reacts also with heterocyclic dienophiles such as 3-sulfolene to the corresponding Diels-Alder adduct.M.P. Cava J.P. VanMeter Journal of Organic Chemistry Condensed cyclobutane aromatic compounds. XXX. Synthesis of some unusual 2,3-naphthoquinonoid heterocycles. A synthetic route to derivatives of naphtho[2,3-b]biphenylene and anthra[b]cyclobutene 34 3 538–545 1969 10.1021/jo01255a012 Molecular building block for polyaromatics Polyaromatic hydrocarbons (PAHs) are of interest as precursors to graphite but also raise concern as ingredients of pollution. They have persistence and carcinogenicity. 1,3-diphenylisobenzofuran reacts quantitatively with acenaphthylene when heated to 160 °C to give 7,12-diphenylbenzo[k]fluoranthene.Houben-Weyl Science of Synthesis 45b Compounds with All-Carbon Functions Thieme Stuttgart 1038 978-3-13-146551-1 2009 400px|center|Reaktion von 1,3-Diphenylisobenzofuran mit Acenaphthylen The twice occurring Diels-Alder reaction of 1,3-diphenylisobenzofuran with p-benzoquinone yields almost quantitatively a product that can be reacted further with p-toluenesulfonic acid to give a pentacene derivative in 49% yield.G. P. Miller J. Briggs Andreas J. Athans The Exciting World of Nanocages and Nanotubes: Proceedings of the International Symposium on Fullerenes, Nanotubes, and Carbon Nanoclusters Electrochemical Society Proceedings Progress towards the synthesis of tris- and tetrakis[60]fullerene adducts https://books.google.com/books?id=KrtqBzQVO00C PV 2002-12 279–284 1-56677-333-4 2002 The Electrochemical Society 400px|center|Reaktion von 1,3-Diphenylisobenzofuran zum Pentacen Literature W. Friedrichsen Advances in Heterocyclic Chemistry Benzo[c]furans 26 135–234 1980 10.1016/S0065-2725(08)60141-5 9780120206261 W. Friedrichsen Advances in Heterocyclic Chemistry Recent Advances in the Chemistry of Benzo[c]furans and Related Compounds 73 1–96 1999 10.1016/S0065-2725(08)60940-X 9780120207732 R. Rodrigo Progress in the chemistry of isobenzofurans Tetrahedron 44 8 2093–2135 1988 10.1016/S0040-4020(01)81720-8 References Category:Isobenzofurans