9,10-二溴蒽

9,10-二溴蒽
	IUPAC名; 9,10-Dibromoanthracene
英文名	9,10-Dibromoanthracene
识别
CAS号	523-27-3
PubChem	68226
ChemSpider	61529
SMILES	C1=CC=C2C(=C1)C(=C3C=CC=CC3=C2Br)Br;
性质
化学式	C14H8Br2
摩尔质量	336.02 g·mol−1
外观	黄色晶体
密度	1.983 g·cm−3
熔点	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）
危险性
	GHS危险性符号;
GHS提示词	警告
H-术语	H315, H319, H335, H400, H410
P-术语	P261, P264, P271, P273, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P391
相关物质
相关化学品	9-溴蒽; 9,10-二苯蒽
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

9,10-二溴蒽是一种有机化合物，化学式为C₁₄H₈Br₂，它是二溴蒽的同分异构体之一。它于1923年首次被合成，也是第一个通过原子力显微镜和扫描隧道显微镜观测到化学反应的单分子。^[5]

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合成及性质

9,10-二溴蒽可由蒽和溴在三氯甲烷中反应得到，反应结束后蒸去溶剂，在二氯甲烷中重结晶，可以得到黄色针状晶体。^[6]

它在电激发下发出蓝光。^[7]

反应

9,10-二溴蒽的C–Br键在扫描隧道显微镜尖端的电压脉冲中断裂，在该条件下，它先后生成单、双自由基，并通过伯格曼环化反应生成二炔。^[8]

9,10-二溴蒽在乙醚中和正丁基锂反应，生成9-锂-10-溴蒽（乙醚合物二聚体）。^[6]它可以被金属铟在1-丁基-3-甲基咪唑𬭩溴化物（德语：1-Butyl-3-methylimidazoliumbromid）脱溴，得到9-溴蒽。^[9]在碱存在及镍或钯催化剂催化下，它可以和苯硼酸发生铃木-宫浦偶联反应，生成9,10-二苯蒽。^[10]

它和红磷在KOH·0.5H₂O/DMSO超碱体系中加热反应，可以得到9,10-二氢蒽。^[11]

参考文献

[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 （英语）.
[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 （德语）.
[3]
Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (C) 1994-2021 ACD/Labs. SciFinder （英语）.
[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 （英语）.
[5]
9,10-Dibromoanthracene. American Chemical Society. 2016-04-25 [2021-09-10]. （原始内容存档于2020-07-21）（英语）.
[6]
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 （英语）.
[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 （英语）.
[8]
Borman, Stu. Chemists Nudge Molecule To React Then Watch Bonds Break And Form 94 (5). 2016: 7 [2021-09-10]. （原始内容存档于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 （英语）.
[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 （英语）.
[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 （英语）.

[1] [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 （英语）.

[2] [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 （德语）.

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

[4] [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 （英语）.

[motw-5] [5]
9,10-Dibromoanthracene. American Chemical Society. 2016-04-25 [2021-09-10]. （原始内容存档于2020-07-21）（英语）.

[Stern-6] [6]
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 （英语）.

[7] [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 （英语）.

[8] [8]
Borman, Stu. Chemists Nudge Molecule To React Then Watch Bonds Break And Form 94 (5). 2016: 7 [2021-09-10]. （原始内容存档于2021-09-10）.

[9] [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 （英语）.

[10] [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 （英语）.

[11] [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 （英语）.

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