9,10-二溴蒽

9,10-二溴蒽
	IUPAC名; 9,10-Dibromoanthracene
英文名	9,10-Dibromoanthracene
識別
CAS號	523-27-3
PubChem	68226
ChemSpider	61529
SMILES	C1=CC=C2C(=C1)C(=C3C=CC=CC3=C2Br)Br;
性質
化學式	C14H8Br2
摩爾質量	336.02 g·mol−1
外觀	黃色晶體
密度	1.983 g·cm−3
熔點	225—226 °C（498—499 K）
溶解性	5.7×10−5 g·L−1（水，25 °C）; 12.10 g·L−1（甲苯，23 °C）
危險性
	GHS危險性符號;
GHS提示詞	警告
H-術語	H315, H319, H335, H400, H410
P-術語	P261, P264, P271, P273, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P391
相關物質
相關化學品	9-溴蒽; 9,10-二苯蒽
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

9,10-二溴蒽是一種有機化合物，化學式為C₁₄H₈Br₂，它是二溴蒽的同分異構體之一。它於1923年首次被合成，也是第一個透過原子力顯微鏡和掃描隧道顯微鏡觀測到化學反應的單分子。^[5]

合成及性質

9,10-二溴蒽可由蒽和溴在三氯甲烷中反應得到，反應結束後蒸去溶劑，在二氯甲烷中重結晶，可以得到黃色針狀晶體。^[6]

它在電激發下發出藍光。^[7]

反應

9,10-二溴蒽的C–Br鍵在掃描隧道顯微鏡尖端的電壓脈衝中斷裂，在該條件下，它先後生成單、雙自由基，並通過伯格曼環化反應生成二炔。^[8]

9,10-二溴蒽在乙醚中和正丁基鋰反應，生成9-鋰-10-溴蒽（乙醚合物二聚體）。^[6]它可以被金屬銦在1-丁基-3-甲基咪唑鎓溴化物（德語：1-Butyl-3-methylimidazoliumbromid）脫溴，得到9-溴蒽。^[9]在鹼存在及鎳或鈀催化劑催化下，它可以和苯硼酸發生鈴木-宮浦偶聯反應，生成9,10-二苯蒽。^[10]

它和紅磷在KOH·0.5H₂O/DMSO超鹼體系中加熱反應，可以得到9,10-二氫蒽。^[11]

參考文獻

^ Trotter, J. Refinements of the structures of 9,10-dibromo- and 9,10-dichloroanthracene. Acta Crystallographica Section C Crystal Structure Communications (International Union of Crystallography (IUCr)). 1986-07-01, 42 (7): 862–864. ISSN 0108-2701. doi:10.1107/s0108270186094271 （英語）.
^ Wittig, Georg; Harle, Horst; Knauss, Erhard; Niethammer, Konrad. Synthesis of derivatives of triptycene and isoazatriptycene. Chemische Berichte. 1960, 93: 951–962. ISSN 0009-2940 （德語）.
^ Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (C) 1994-2021 ACD/Labs. SciFinder （英語）.
^ Seo, Tamae; Toyoshima, Naoki; Kubota, Koji; Ito, Hajime. Tackling Solubility Issues in Organic Synthesis: Solid-State Cross-Coupling of Insoluble Aryl Halides. Journal of the American Chemical Society (American Chemical Society (ACS)). 2021-03-30, 143 (16): 6165–6175. ISSN 0002-7863. doi:10.1021/jacs.1c00906 （英語）.
^ 9,10-Dibromoanthracene. American Chemical Society. 2016-04-25 [2021-09-10]. （原始內容存檔於2020-07-21）（英語）.
^ ^6.0 ^6.1 Stern, Daniel; Finkelmeier, Nils; Meindl, Kathrin; Henn, Julian; Stalke, Dietmar. Consecutive Donor-Base Exchange in Anthracenyllithium Compounds. Angewandte Chemie International Edition (Wiley). 2010-08-02, 49 (38): 6869–6872. ISSN 1433-7851. doi:10.1002/anie.201002873 （英語）.
^ Brar, Sukhwinder Singh; Mahajan, Aman; Bedi, R. K. Structural, optical and electrical characterization of hot wall grown 9,10-dibromoanthracene films for light emitting applications. Electronic Materials Letters. 10 January 2014, 10 (1): 199–204. S2CID 135788635. doi:10.1007/s13391-013-3153-8 （英語）.
^ Borman, Stu. Chemists Nudge Molecule To React Then Watch Bonds Break And Form 94 (5). 2016: 7 [2021-09-10]. （原始內容存檔於2021-09-10）.
^ Cañete, Álvaro; Salas, Cristian; Zacconi, Flavia. Efficient Indium-Mediated Dehalogenation of Aromatics in Ionic Liquid Media. Molecules (MDPI AG). 2012-12-28, 18 (1): 398–407. ISSN 1420-3049. doi:10.3390/molecules18010398 （英語）.
^ Talukder, Md Muktadir; Cue, John Michael O.; Miller, Justin T.; Gamage, Prabhath L.; Aslam, Amina; McCandless, Gregory T.; Biewer, Michael C.; Stefan, Mihaela C. Ligand Steric Effects of α-Diimine Nickel(II) and Palladium(II) Complexes in the Suzuki–Miyaura Cross-Coupling Reaction. ACS Omega (American Chemical Society (ACS)). 2020-09-10, 5 (37): 24018–24032. ISSN 2470-1343. doi:10.1021/acsomega.0c03415 （英語）.
^ Kuimov, Vladimir A.; Gusarova, Nina K.; Malysheva, Svetlana F.; Trofimov, Boris A. Transition metal-free regioselective access to 9,10-dihydroanthracenes via the reaction of anthracenes with elemental phosphorus in the KOH/DMSO system. Tetrahedron Letters (Elsevier BV). 2018, 59 (52): 4533–4536. ISSN 0040-4039. doi:10.1016/j.tetlet.2018.10.075 （英語）.

[1] Trotter, J. Refinements of the structures of 9,10-dibromo- and 9,10-dichloroanthracene. Acta Crystallographica Section C Crystal Structure Communications (International Union of Crystallography (IUCr)). 1986-07-01, 42 (7): 862–864. ISSN 0108-2701. doi:10.1107/s0108270186094271 （英語）.

[2] Wittig, Georg; Harle, Horst; Knauss, Erhard; Niethammer, Konrad. Synthesis of derivatives of triptycene and isoazatriptycene. Chemische Berichte. 1960, 93: 951–962. ISSN 0009-2940 （德語）.

[3] Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (C) 1994-2021 ACD/Labs. SciFinder （英語）.

[4] Seo, Tamae; Toyoshima, Naoki; Kubota, Koji; Ito, Hajime. Tackling Solubility Issues in Organic Synthesis: Solid-State Cross-Coupling of Insoluble Aryl Halides. Journal of the American Chemical Society (American Chemical Society (ACS)). 2021-03-30, 143 (16): 6165–6175. ISSN 0002-7863. doi:10.1021/jacs.1c00906 （英語）.

[motw-5] 9,10-Dibromoanthracene. American Chemical Society. 2016-04-25 [2021-09-10]. （原始內容存檔於2020-07-21）（英語）.

[Stern-6] 6.0 ^6.1 Stern, Daniel; Finkelmeier, Nils; Meindl, Kathrin; Henn, Julian; Stalke, Dietmar. Consecutive Donor-Base Exchange in Anthracenyllithium Compounds. Angewandte Chemie International Edition (Wiley). 2010-08-02, 49 (38): 6869–6872. ISSN 1433-7851. doi:10.1002/anie.201002873 （英語）.

[7] Brar, Sukhwinder Singh; Mahajan, Aman; Bedi, R. K. Structural, optical and electrical characterization of hot wall grown 9,10-dibromoanthracene films for light emitting applications. Electronic Materials Letters. 10 January 2014, 10 (1): 199–204. S2CID 135788635. doi:10.1007/s13391-013-3153-8 （英語）.

[8] Borman, Stu. Chemists Nudge Molecule To React Then Watch Bonds Break And Form 94 (5). 2016: 7 [2021-09-10]. （原始內容存檔於2021-09-10）.

[9] Cañete, Álvaro; Salas, Cristian; Zacconi, Flavia. Efficient Indium-Mediated Dehalogenation of Aromatics in Ionic Liquid Media. Molecules (MDPI AG). 2012-12-28, 18 (1): 398–407. ISSN 1420-3049. doi:10.3390/molecules18010398 （英語）.

[10] Talukder, Md Muktadir; Cue, John Michael O.; Miller, Justin T.; Gamage, Prabhath L.; Aslam, Amina; McCandless, Gregory T.; Biewer, Michael C.; Stefan, Mihaela C. Ligand Steric Effects of α-Diimine Nickel(II) and Palladium(II) Complexes in the Suzuki–Miyaura Cross-Coupling Reaction. ACS Omega (American Chemical Society (ACS)). 2020-09-10, 5 (37): 24018–24032. ISSN 2470-1343. doi:10.1021/acsomega.0c03415 （英語）.

[11] Kuimov, Vladimir A.; Gusarova, Nina K.; Malysheva, Svetlana F.; Trofimov, Boris A. Transition metal-free regioselective access to 9,10-dihydroanthracenes via the reaction of anthracenes with elemental phosphorus in the KOH/DMSO system. Tetrahedron Letters (Elsevier BV). 2018, 59 (52): 4533–4536. ISSN 0040-4039. doi:10.1016/j.tetlet.2018.10.075 （英語）.

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