CAS: 92-24-0; Naphthacene

该化合物是一个由五根引信苯环组成的多环芳烃(PAH),形成线性结构,在室温下是固体,通常看起来像一种黄到褐结晶物质.纳phthacene以其高度稳定性和相对较高的熔点而著称,与其他PAHs相比,它具有很强的荧光性,并具有潜在应用于有机电子产品,特别是有机发光二极管(OLEDs)和有机光伏,因其有利的电子特性.该化合物在水中不溶,但在苯和甲苯等有机溶剂中是溶解的.纳phtacene可以经历典型的芳香化合物的各种化学反应,包括电益替代.然而,必须小心处理它,因为许多PAHAH被视为环境污染物,并可能对接触时造成健康风险.

结构式图片

物理性质

MSDS等安全信息

欧盟法规

ECHA物质ECHA物质C&L通报REACH预注册

上下游产品

5,12-dihydro-naphthacene 6-hydroxy-naphthacene-5,12-dione tetrahydro-1,2,3,4 naphtacene 5,11-dichlorotetracene5,12-naphthacenequinone 5,12-dihydro-naphthacene 5,11-dibromonaphthacene tetrathiatetracene

合成工艺路线路线简述

  • 合成目标产物 Naphthacene 主要起始原料 5,12-Dihydronaphthacene
  • 959-02-4 = 92-24-0
    反应条件:1.1 Reagents: Copper
    标题:Aromatic Hydrocarbons. Xxiv. Hexacene,A Green Simple Hydrocarbon
    作者:Clar,E.
    参考文献:Berichte Der Deutschen Chemischen Gesellschaft [abteilung] B: Abhandlungen 日期:1939 卷标:72 页码:1817-21]

    179474-27-2 = 92-24-0
    反应条件:1.1 Reagents: Hydrochloric Acid,Stannous Chloride
    标题:Synthesis Of Geometrically Well-Defined Covalent Acene Dimers For Mechanistic Exploration Of Singlet Fission
    作者:Carey,Thomas J.; Snyder,Jamie L.; Miller,Ethan G.; Sammakia,Tarek; Damrauer,Niels H.
    参考文献:Journal Of Organic Chemistry 日期:2017 卷标:82(9) 页码:4866-4874]

    1598372-64-5 = 92-24-0
    反应条件:1.1 Reagents: Sodium Sulfite Catalysts: 1-Butanaminium,N,N,N-Tributyl-,(Tb-5-11)-Dioxo[2,6-Pyridinedicarboxylato(2-)-K... Solvents: Benzene; 96 H,180 °C; 180 °C -> Rt1.2 Reagents: Oxygen; 72 H,1 Atm,80 °C
    标题:Benzannulation Via Ruthenium-Catalyzed Diol-Diene [4+2] Cycloaddition: One- And Two-Directional Syntheses Of Fluoranthenes And Acenes
    作者:Geary,Laina M.; Chen,Te-Yu; Montgomery,T. Patrick; Krische,Michael J.
    参考文献:Journal Of The American Chemical Society 日期:2014 卷标:136(16) 页码:5920-5922]

    1426414-15-4 = 92-24-0
    反应条件:1.1 Reagents: Poly(Methyl Methacrylate) Solvents: Toluene; Overnight,Rt1.2 Solvents: Dichloromethane1.3 1 H,Rt
    标题:Photochemical Synthesis Of Naphthacene And Its Derivatives For Irreversible Photo-Responsive Fluorescent Molecules
    作者:Aotake,Tatsuya; Yamashita,Yuko; Okujima,Tetsuo; Shirasawa,Nobuhiko; Jo,Yukari; Et Al
    参考文献:Tetrahedron Letters 日期:2013 卷标:54(14) 页码:1790-1793]

    = 92-24-0
    反应条件:1.1 Reagents: Gallium Chloride
    标题:Oxidation Of Arenes By Molten Gallium(Iii) Chloride
    作者:Dworkin,A. S.; Brown,L. L.; Buchanan,A. C. Iii; Smith,G. P.
    参考文献:Tetrahedron Letters 日期:1985 卷标:26(23) 页码:2727-30]

    96965-72-9 = 92-24-0
    反应条件:1.1 Reagents: Trifluoroacetic Acid Solvents: Chloroform
    标题:Twin Benzannulation Of Naphthalene Via 1,3-,1,6-,And 2,6-Naphthodiyne Synthetic Equivalents. New Syntheses Of Triphenylene,Benz[a]Anthracene,And Naphthacene
    作者:Gribble,Gordon W.; Perni,Robert B.; Onan,Kay D.
    参考文献:Journal Of Organic Chemistry 日期:1985 卷标:50(16) 页码:2934-9]

    = 92-24-0 [标题:Reaction Conditions
    标题:Formation Of C60 And Polycyclic Aromatic Hydrocarbons Upon Electric Discharges In Liquid Toluene
    作者:Beck,Mihaly T.; Dinya,Zoltan; Keki,Sandor; Papp,Lajos
    参考文献:Tetrahedron 日期:1993 卷标:49(1) 页码:285-90]

    = 92-24-0 [标题:Reaction Conditions
    标题:Electrochemical Reactions Of Carbonyl Compounds In The Presence Of Ethanethiol
    作者:Tamano,Michiko; Nishio,Shoji; Fujimura,Yoshikazu; Koketsu,Jugo
    参考文献:Nippon Kagaku Kaishi 日期:1990 卷标:(4) 页码:391-5]

    = 92-24-0 [标题:Reaction Conditions
    标题:Method Of Producing Tetracene
    参考文献:Ussr]

    959-02-4 = 92-24-0
    反应条件:1.1 Catalysts: Palladium Solvents: Xylene
    标题:Linear Acene Derivatives. New Routes To Pentacene And Naphthacene And The First Synthesis Of A Triptycene With Two Anthracene Moieties
    作者:Luo,Jihmei; Hart,Harold
    参考文献:Journal Of Organic Chemistry 日期:1987 卷标:52(22) 页码:4833-6]

    959-02-4 = 92-24-0 [标题:Reaction Conditions
    标题:Hydride Eliminations. 6. Deprotonation-Hydride Elimination As A Method For Dehydrogenation
    作者:Reetz,Manfred T.; Eibach,Franz
    参考文献:Angewandte Chemie 日期:1978 卷标:90(4) 页码:285-6]

    2095307-74-5 = 92-24-0
    反应条件:1.1 Reagents: Titanium Tetrachloride Solvents: 1,2-Dichloroethane; 1 Min,0 °C; 3 H,0 °C -> 40 °C
    标题:Straightforward Synthesis Of 2- And 2,8-Substituted Tetracenes
    作者:Woodward,Simon; Ackermann,Miriam; Ahirwar,Saurabh K.; Burroughs,Laurence; Garrett,Mary Robert; Et Al
    参考文献:Chemistry - A European Journal 日期:2017 卷标:23(32) 页码:7819-7824]

    179474-27-2 = 92-24-0
    反应条件:1.1 Reagents: Hydrochloric Acid,Stannous Chloride Solvents: Tetrahydrofuran; Rt; 1 H,Rt
    标题:Electron Acceptors Based On Cyclopentannulated Tetracenes
    作者:Kulkarni,Gajanan C.; Morales-Cruz,Jean L.; Hussain,Waseem A.; Garvey,Ian J.; Plunkett,Kyle N.
    参考文献:Synlett 日期:2018 卷标:29(19) 页码:2572-2576]

    256439-92-6 = 92-24-0
    反应条件:1.1 Reagents: Sodium Methoxide Solvents: Methanol,Tetrahydrofuran1.2 Solvents: Benzene
    标题:A Reiterative Approach To 2,3-Disubstituted Naphthalenes And Anthracenes
    作者:Bowles,Daniel M.; Anthony,John E.
    参考文献:Organic Letters 日期:2000 卷标:2(1) 页码:85-87]

    179474-26-1 = 92-24-0
    反应条件:1.1 Reagents: Aluminum Catalysts: Mercuric Chloride Solvents: Carbon Tetrachloride,Cyclohexanol; Rt -> 80 °C; 3 H,100 °C1.2 48 H,150 °C
    标题:Synthesis And Characterization Of 5,5'-Bitetracene
    作者:Mamada,Masashi; Goushi,Kenichi; Nakamura,Ryota; Kaji,Hironori; Adachi,Chihaya
    参考文献:Chemistry Letters 日期:2021 卷标:50(4) 页码:800-803]

    694-87-1 + 573-57-9 = 92-24-0 [标题:Reaction Conditions
    标题:Synthesis Of Naphthalenes,Anthracenes,9H-Fluorenes,And Other Acenes
    作者:Toyota,S.; Iwanaga,T.
    参考文献:Science Of Synthesis 日期:2010 卷标:45 页码:745-854]

    = 92-24-0
    反应条件:1.1 112 - 115 °C
    标题:Carbonyl-Bridged Acenes And Hydroxymethylene-Bridged Acenes,Preparation Thereof,And Manufacture Of Nonbridged Acenes Therefrom
    参考文献:Japan]

    3073-99-2 = 92-24-0
    反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran
    标题:Isobenzofuran-Aryne Cycloadducts: Formation And Regioselective Conversion To Anthrones And Substituted Polycyclic Aromatics
    作者:Netka,Jill; Crump,Stephen L.; Rickborn,Bruce
    参考文献:Journal Of Organic Chemistry 日期:1986 卷标:51(8) 页码:1189-99]

    65957-28-0 = 92-24-0
    反应条件:1.1 Catalysts: 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone
    标题:Diels-Alder Approach To Naphthocyclobutenes And Anthrocyclobutenes
    作者:Thummel,Randolph P.; Cravey,Wesley E.; Nutakul,Wutichai
    参考文献:Journal Of Organic Chemistry 日期:1978 卷标:43(12) 页码:2473-7]

    = 92-24-0 [标题:Reaction Conditions
    标题:A Convenient Generation Of 2,3-Naphthalyne. Linear Annulation Of Naphthalene And A New Naphthacene Synthesis
    作者:Lehoullier,Craig S.; Gribble,Gordon W.
    参考文献:Journal Of Organic Chemistry 日期:1983 卷标:48(14) 页码:2364-6
📜2,3-Diethynylanthracene置于1,4-环己二烯体系中,用 苯 作为反应溶剂,160.0 °C,1.65 Mpa 条件下,以64%的收率获得产物并四苯
参考文献:2,3-二取代萘和蒽的迭代方法
标题:2,3-二取代萘和蒽的迭代方法
摘要:[反应:见正文]简单的双(溴乙炔基)亚芳基二炔很容易通过相应三甲基甲硅烷基衍生物的脱甲硅烷基卤化反应制得.这些卤代二炔的芳环芳香化导致否则难以以高收率制备2,3-二溴芳烃.所得卤代芳族化合物的炔基化可再生可溶的二炔体系,该体系被一个芳香环所同源.该迭代方法可以通过未取代的二炔的环芳构化来终止,从而提供简单的并苯烃.
DOI:10.1021/ol991254W

海关参考信息

专利信息


专利号:US-2024092821-A1
优先权日:2020-03-31
标题:Synthesis of oligonucleotides and related compounds
发明人：ZHONG MINGHONG; JIN YI; GALA DINESH; PRHAVC MARIJA
权利人:JANSSEN BIOPHARMA INC
摘要:Methods of synthesizing oligonucleotides via new intermediates on a cleavable support having an azidomethyl moiety are disclosed. The method comprises multiple reaction cycles, each of which comprises sequential coupling a nucleoside or oligonucleotide subunit on a cleavable support having an azidomethyl moiety and a nucleoside phosphoramidite or an oligonucleotide phosphoramidite, capping, oxidation/thiolation and deblocking; followed by orthogonal cleavage of the azidomethyl support while keeping all other protecting groups intact. The method can be used in combination with a support moiety for either solid phase or liquid phase oligo synthesis. The soluble support facilitates homogeneous reactions and efficient separations by simple precipitation. The methods also provide novel intermediates useful in the synthesis of oligonucleotide conjugates.

专利号:US-10711138-B2
优先权日:2016-04-08
标题:Intermediates and procedures for the synthesis of functional materials
发明人：KIRSCH PEER; GUNST SUSANN
权利人:MERCK PATENT GMBH
摘要:The present invention relates to heteroaromatic compounds which have two different reactive groups, their use in the synthesis of asymmetrically substituted compounds, and synthesis processes in which the compounds according to the invention are reacted sequentially with two different compounds, whereby an asymmetrically substituted compound is formed.

专利号:US-10889599-B2
优先权日:2018-02-27
标 题:1,1-diborylalkyl-1-metal compounds, preparation method thereof, and their applications toward synthesis of 1,1-diboronate ester compounds
发明人：CHO SEUNG HWAN; LEE YEOSAN
权利人:POSTECH ACAD IND FOUND
摘要:The present invention relates to a 1,1-diborylalkyl-1-metal compound including one metal group together with two identical boron groups at the sp3 carbon center, and its use. Specifically, the present invention relates to development of novel organic reactions, synthesis of functional molecules, and synthesis of new drugs by applying the novel 1,1-diboryl-1-metal substituted alkyl compounds to various molecular libraries which could not be synthesized by conventional methodologies.

专利号:US-6022963-A
优先权日:1995-12-15
标 题:Synthesis of oligonucleotide arrays using photocleavable protecting groups
发明人：MCGALL GLENN H; NAM NGO QUOC
权利人:AFFYMETRIX INC
摘要:Novel compounds are provided which are useful as linking groups in chemical synthesis, preferably in the solid phase synthesis of oligonucleotides and polypeptides. These compounds are generally photolabile and comprise protecting groups which can be removed by photolysis to unmask a reactive group. The protecting group has the general formula Ar-C(R1)(R2)-O-C(O)- wherein: Ar is an optionally substituted fused polycyclic aryl or heteroaromatic group or a vinylogous derivative thereof; R1 and R2 are independently H, optionally substituted alkyl, alkenyl or alkynyl, optionally substituted aryl or optionally substituted heteroaromatic, or a vinylogous derivative of the foregoing; and X is a leaving group, a chemical fragment linked to Ar-C(R1)(R2)-O-C(O)- via a heteroatom, or a solid support; provided that when Ar is 1-pyrenyl and R1=R2=H, X is not linked to Ar-C(R1)(R2)-O-C(O)- via a nitrogen atom. Preferred embodiments are those in which Ar is a fused polycyclic aromatic hydrocarbon and in which the substituents on Ar, R1 and R2 are electron donating groups. A particularly preferred protecting group is the 'PYMOC' protecting group, pyrenylmethyloxycarbonyl, where Ar=pyrenyl and R1=R2=H. Also provided is a method of forming, from component molecules, a plurality of compounds on a support, each compound occupying a separate predefined region of the support, using the protected compounds described above.

专利号:US-2010087658-A1
优先权日:1996-08-06
标 题 :Methods and intermediates for synthesis of selective dpp-iv inhibitors
发明人：CAMPBELL DAVID ALAN; LEITAO EMILIA P T; WU ZHEN-PING; WANG PENG
权利人:PHENOMIX CORP
摘要:Methods and intermediates for the synthesis of selective inhibitors of dipeptidyl peptidase IV (DPP-IV) are provided. Coupling of a carboxylate salt with a boro-proline derivative provides a protected form of a DPP-IV inhibitor, which may be deblocked to yield the medicinal compound. The carboxylate salt can be a crystalline form of a sodium salt or a dicyclohexylammonium salt. The inhibitor can be used in the treatment of diabetes.

专利号:US-9000209-B2
优先权日:2011-07-22
标题:Method of regioselective synthesis of substituted benzoates
发明人：KRAUS GEORGE A
权利人:KRAUS GEORGE A; UNIV IOWA STATE RES FOUND INC
摘要:A method of synthesis of para-substituted benzoate esters and acids is provided, wherein the para-substituted regioisomer is obtained substantially free of the meta-substituted impurity, the method comprising contacting a coumalate ester or acid and an unactivated alkene at elevated temperature in the presence of a metal oxidation catalyst and an oxidant. The metal oxidation catalyst can be palladium, such as palladium on carbon, and the oxidant can be the oxygen gas in ambient air. The reaction can be carried out without solvent or in high boiling hydrocarbon solvents such as mesitylene. When the unactivated alkene is a monosubstituted alkene, yields of at least about 50 or 60% of para-substituted ester and acid products, respectively, are obtained, substantially free of the regioisomeric meta-substituted impurity.

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合成参考文献


摘要:Toyota, S.; Iwanaga, T., Science of Synthesis, (2010) 45, 840.
摘要:Dai, X.; Shi, F., Science of Synthesis: Catalytic Reduction in Organic Synthesis, (2017) 1, 145.
摘要:T. Handa and M. Kobayashi. Yoki Gosei Kagaku Kyokai Shi 13, 580 (1955); 14, 337, 550 (1956); CA 51, 8439d.
摘要:A10: Santodonato J, Howard P, Basu D: Health and ecological assessment of polynuclear aromatic hydrocarbons. J Environ Pathol Toxicol. 1981 Sep;5(1):1-364.
摘要:Fogel, M. S.; Shellnutt, Z. S.; Koide, K., Science of Synthesis: Dearomatizations, (2026) .
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