二氯二苯甲烷

二氯二苯甲烷
	IUPAC名; 1,1′-(Dichloromethylene)dibenzene
別名	二苯二氯甲烷; 二氯二苯基甲烷; α,α-二氯二苯甲烷
識別
CAS號	2051-90-3
PubChem	16327
ChemSpider	15492
SMILES	c1ccc(cc1)C(c2ccccc2)(Cl)Cl;
Beilstein	1910601
性質
化學式	C13H10Cl2
摩爾質量	237.12 g·mol−1
外觀	無色固體
密度	1.235 g/cm3
熔點	146—150 °C（419—423 K）
沸點	193 °C（466 K）（32 torr）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

二氯二苯甲烷是一種有機化合物，化學式為(C₆H₅)₂CCl₂，是一種無色固體。它可由四氯化碳和苯在無水三氯化鋁催化下發生付克烷基化反應得到。^[3]它也可由二苯基甲酮和五氯化磷反應製得：^[4]

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

反應

二氯二苯甲烷和1,1'-二硫代二[1,1-二苯基硫化磷]及鋰在四氫呋喃中反應，可以得到二苯基二硫代次膦酸二苯基亞甲酯。^[5]它和銅粉在二甲基亞碸中反應，可以得到四苯基乙烯。^[6]

它和硫氰酸銨在二氧化硫中反應，可以得到二異氰基二苯基甲烷；^[7]它和疊氮化鈉在乙腈中反應，可以得到二疊氮二苯甲烷。^[8]

參考文獻

^ 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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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 （俄語）. 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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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 （俄語）. 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. （原始內容存檔於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. （原始內容存檔於2020-07-05）.

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