二氯二苯甲烷

二氯二苯甲烷
	IUPAC名; 1,1′-(Dichloromethylene)dibenzene
别名	二苯二氯甲烷; 二氯二苯基甲烷; α,α-二氯二苯甲烷
识别
CAS号	2051-90-3
PubChem	16327
ChemSpider	15492
SMILES	c1ccc(cc1)C(c2ccccc2)(Cl)Cl;
Beilstein	1910601
性质
化学式	C13H10Cl2
摩尔质量	237.12 g·mol−1
外观	无色固体
密度	1.235 g/cm3
熔点	146—150 °C（419—423 K）
沸点	193 °C（466 K）（32 torr）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

二氯二苯甲烷是一种有机化合物，化学式为(C₆H₅)₂CCl₂，是一种无色固体。它可由四氯化碳和苯在无水三氯化铝催化下发生付克烷基化反应得到。^[3]它也可由二苯基甲酮和五氯化磷反应制得：^[4]

(C₆H₅)₂CO + PCl₅ → (C₆H₅)₂CCl₂ + POCl₃

反应

二氯二苯甲烷和1,1'-二硫代二[1,1-二苯基硫化磷]及锂在四氢呋喃中反应，可以得到二苯基二硫代次膦酸二苯基亚甲酯。^[5]它和铜粉在二甲基亚砜中反应，可以得到四苯基乙烯。^[6]

它和硫氰酸铵在二氧化硫中反应，可以得到二异氰基二苯基甲烷；^[7]它和叠氮化钠在乙腈中反应，可以得到二叠氮二苯甲烷。^[8]

参考文献

^ Ballester, Manuel; Juan Riera-Figueras; Juan Castaner; Carlos Badfa; Jose M. Monso. Inert carbon free radicals. I. Perchlorodiphenylmethyl and perchlorotriphenylmethyl radical series. Journal of the American Chemical Society. 1971, 93 (9): 2215–2225 [2023-09-10]. ISSN 0002-7863. doi:10.1021/ja00738a021. （原始内容存档于2023-02-13）.
^ Andrews, L. J.; W. W. Kaeding. The Formation of Benzophenone and its Diethylketal in the Ethanolysis of Diphenyldichloromethane. Journal of the American Chemical Society. 1951, 73 (3): 1007–1011 [2023-09-10]. ISSN 0002-7863. doi:10.1021/ja01147a036. （原始内容存档于2023-02-13）.
^ Marvel, C. S. (1941). "Benzophenone". Org. Synth.; Coll. Vol. 1: 95.
^ Spaggiari, Alberto; Daniele Vaccari; Paolo Davoli; Giovanni Torre; Fabio Prati. A Mild Synthesis of Vinyl Halides andgem-Dihalides Using Triphenyl Phosphite−Halogen-Based Reagents. The Journal of Organic Chemistry. 2007, 72 (6): 2216–2219 [2023-09-10]. ISSN 0022-3263. PMID 17295542. doi:10.1021/jo061346g. （原始内容存档于2023-02-11）.
^ Torgasheva, N. A.; Khaskin, B. A.; Ishmuratov, A. S. Reaction of phosphorus-containing disulfides with aryldiazoalkanes and aryl carbenes. Zhurnal Obshchei Khimii. 1991, 61 (6): 1325–1328. ISSN 0044-460X （俄语）. CODEN ZOKHA4
^ Yasuyuki Tezuka, Akio Hashimoto, Koh Ushizaka, and Kiyokazu Imai. Generation and reactions of novel copper carbenoids through a stoichiometric reaction of copper metal with gem-dichlorides in dimethyl sulfoxide. The Journal of Organic Chemistry. 1990, 55 (1): 329–333 [2023-09-10]. doi:10.1021/jo00288a056. （原始内容存档于2023-11-19）.
^ Atef Hamed, Edgar Müller, Mahmoud Al-Talib, Johannes C. Jochims. On the Reactions of a-Chlorocarbenium Ions with Ammonium Thiocyanate and Potassium Cyanate. Synthesis. 1987, (8): 745–748. doi:10.1055/s-1987-28073.
^ Barash, Louis; Wasserman, Edel; Yager, William A. Generation of methylenes from germinal diazides via excited nitrenes. Journal of the American Chemical Society. 1967, 89 (15): 3931–3932 [2023-09-10]. ISSN 0002-7863. doi:10.1021/ja00991a063. （原始内容存档于2020-07-05）.

[Ballester1971-1] Ballester, Manuel; Juan Riera-Figueras; Juan Castaner; Carlos Badfa; Jose M. Monso. Inert carbon free radicals. I. Perchlorodiphenylmethyl and perchlorotriphenylmethyl radical series. Journal of the American Chemical Society. 1971, 93 (9): 2215–2225 [2023-09-10]. ISSN 0002-7863. doi:10.1021/ja00738a021. （原始内容存档于2023-02-13）.

[Andrews1951-2] Andrews, L. J.; W. W. Kaeding. The Formation of Benzophenone and its Diethylketal in the Ethanolysis of Diphenyldichloromethane. Journal of the American Chemical Society. 1951, 73 (3): 1007–1011 [2023-09-10]. ISSN 0002-7863. doi:10.1021/ja01147a036. （原始内容存档于2023-02-13）.

[Marvel-3] Marvel, C. S. (1941). "Benzophenone". Org. Synth.; Coll. Vol. 1: 95.

[Spaggiari2007-4] Spaggiari, Alberto; Daniele Vaccari; Paolo Davoli; Giovanni Torre; Fabio Prati. A Mild Synthesis of Vinyl Halides andgem-Dihalides Using Triphenyl Phosphite−Halogen-Based Reagents. The Journal of Organic Chemistry. 2007, 72 (6): 2216–2219 [2023-09-10]. ISSN 0022-3263. PMID 17295542. doi:10.1021/jo061346g. （原始内容存档于2023-02-11）.

[5] Torgasheva, N. A.; Khaskin, B. A.; Ishmuratov, A. S. Reaction of phosphorus-containing disulfides with aryldiazoalkanes and aryl carbenes. Zhurnal Obshchei Khimii. 1991, 61 (6): 1325–1328. ISSN 0044-460X （俄语）. CODEN ZOKHA4

[6] Yasuyuki Tezuka, Akio Hashimoto, Koh Ushizaka, and Kiyokazu Imai. Generation and reactions of novel copper carbenoids through a stoichiometric reaction of copper metal with gem-dichlorides in dimethyl sulfoxide. The Journal of Organic Chemistry. 1990, 55 (1): 329–333 [2023-09-10]. doi:10.1021/jo00288a056. （原始内容存档于2023-11-19）.

[7] Atef Hamed, Edgar Müller, Mahmoud Al-Talib, Johannes C. Jochims. On the Reactions of a-Chlorocarbenium Ions with Ammonium Thiocyanate and Potassium Cyanate. Synthesis. 1987, (8): 745–748. doi:10.1055/s-1987-28073.

[8] Barash, Louis; Wasserman, Edel; Yager, William A. Generation of methylenes from germinal diazides via excited nitrenes. Journal of the American Chemical Society. 1967, 89 (15): 3931–3932 [2023-09-10]. ISSN 0002-7863. doi:10.1021/ja00991a063. （原始内容存档于2020-07-05）.

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