1-溴-4-碘苯

1-溴-4-碘苯
英文名	1-bromo-4-iodobenzene
别名	1-碘-4-溴苯; 对溴碘苯
识别
CAS号	589-87-7
SMILES	Ic1ccc(Br)cc1;
性质
化学式	C6H4BrI
摩尔质量	282.9 g·mol−1
熔点	91—92 °C（364—365 K）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

1-溴-4-碘苯是一种有机化合物，化学式为C₆H₄BrI。

制备

1-溴-4-碘苯可由4-溴苯基三氟硼酸钾和三碘化铯在DMF的水溶液中加热反应制得。^[2]4-溴苯重氮盐^[3]或1-溴-4-(三甲基硅基)苯^[4]和碘化钾的反应也可制得1-溴-4-碘苯。

其它制法还包括4-溴苯肼盐酸盐和碘的反应^[5]以及4-溴苯硼酸的碘化反应^[6]。

性质

它和硫、氢氧化锂在DMF中反应（CuI催化），可以得到4,4'-二溴苯硫醚。^[7]它和乙烯基溴化镁反应，可以得到4-溴苯乙烯。^[8]

参考文献

^ Attilio Citterio, Anna Arnoldi. Synthesis of Aryliodides from Diazonium Tetrafluoroborate in Dimethylsulfoxide. Synthetic Communications. 1981-01, 11 (8): 639–642 [2020-10-21]. ISSN 0039-7911. doi:10.1080/00397918108063637 （英语）.
^ Min-Liang Yao, George W. Kabalka, David W. Blevins, Marepally Srinivasa Reddy, Li Yong. Halodeboronation of organotrifluoroborates using tetrabutylammonium tribromide or cesium triiodide. Tetrahedron. 2012-05, 68 (19): 3738–3743 [2020-10-21]. doi:10.1016/j.tet.2012.03.016. （原始内容存档于2018-06-29）（英语）.
^ Somnath S. Gholap. An Efficient Gram Scale Synthesis of Aryl Iodides from Aryl Diazofluoroborates in Water under Mild Conditions. Letters in Organic Chemistry. 2018-06-13, 15 (7): 594–599 [2020-10-21]. doi:10.2174/1570178614666170907120329. （原始内容存档于2020-01-23）（英语）.
^ Robert Möckel, Jessica Hille, Erik Winterling, Stephan Weidemüller, Tabea Melanie Faber, Gerhard Hilt. Electrochemical Synthesis of Aryl Iodides by Anodic Iododesilylation. Angewandte Chemie International Edition. 2018-01-08, 57 (2): 442–445 [2020-10-21]. doi:10.1002/anie.201711293 （英语）.
^ Chun-ping Dong, Kentaro Nakamura, Toshihide Taniguchi, Soichiro Mita, Shintaro Kodama, Shin-ichi Kawaguchi, Akihiro Nomoto, Akiya Ogawa, Takumi Mizuno. Synthesis of Aryl Iodides from Arylhydrazines and Iodine. ACS Omega. 2018-08-31, 3 (8): 9814–9821 [2020-10-21]. ISSN 2470-1343. doi:10.1021/acsomega.8b01559 （英语）.
^ R. H. Tale, G. K. Toradmal, V. B. Gopula. A practical and general ipso iodination of arylboronic acids using N-iodomorpholinium iodide (NIMI) as a novel iodinating agent: mild and regioselective synthesis of aryliodides. RSC Advances. 2015, 5 (103): 84910–84919 [2020-10-21]. ISSN 2046-2069. doi:10.1039/C5RA18820B （英语）.
^ Hsing-Ying Chen, Wei-Te Peng, Ying-Hsien Lee, Yu-Lun Chang, Yen-Jen Chen, Yi-Chun Lai, Nai-Yuan Jheng, Hsuan-Ying Chen. Use of Base Control To Provide High Selectivity between Diaryl Thioether and Diaryl Disulfide for C–S Coupling Reactions of Aryl Halides and Sulfur and a Mechanistic Study. Organometallics. 2013-10-14, 32 (19): 5514–5522 [2020-10-21]. ISSN 0276-7333. doi:10.1021/om400784w （英语）.
^ Bumagin, N. A.; Andryukhova, N. P.; Beletskaya, I. P. Catalyst for cross-coupling of vinylmagnesium bromide with aryl iodides（俄文）. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987. 7: 1681-1682. ISSN: 0002-3353.

[1] Attilio Citterio, Anna Arnoldi. Synthesis of Aryliodides from Diazonium Tetrafluoroborate in Dimethylsulfoxide. Synthetic Communications. 1981-01, 11 (8): 639–642 [2020-10-21]. ISSN 0039-7911. doi:10.1080/00397918108063637 （英语）.

[2] Min-Liang Yao, George W. Kabalka, David W. Blevins, Marepally Srinivasa Reddy, Li Yong. Halodeboronation of organotrifluoroborates using tetrabutylammonium tribromide or cesium triiodide. Tetrahedron. 2012-05, 68 (19): 3738–3743 [2020-10-21]. doi:10.1016/j.tet.2012.03.016. （原始内容存档于2018-06-29）（英语）.

[3] Somnath S. Gholap. An Efficient Gram Scale Synthesis of Aryl Iodides from Aryl Diazofluoroborates in Water under Mild Conditions. Letters in Organic Chemistry. 2018-06-13, 15 (7): 594–599 [2020-10-21]. doi:10.2174/1570178614666170907120329. （原始内容存档于2020-01-23）（英语）.

[4] Robert Möckel, Jessica Hille, Erik Winterling, Stephan Weidemüller, Tabea Melanie Faber, Gerhard Hilt. Electrochemical Synthesis of Aryl Iodides by Anodic Iododesilylation. Angewandte Chemie International Edition. 2018-01-08, 57 (2): 442–445 [2020-10-21]. doi:10.1002/anie.201711293 （英语）.

[5] Chun-ping Dong, Kentaro Nakamura, Toshihide Taniguchi, Soichiro Mita, Shintaro Kodama, Shin-ichi Kawaguchi, Akihiro Nomoto, Akiya Ogawa, Takumi Mizuno. Synthesis of Aryl Iodides from Arylhydrazines and Iodine. ACS Omega. 2018-08-31, 3 (8): 9814–9821 [2020-10-21]. ISSN 2470-1343. doi:10.1021/acsomega.8b01559 （英语）.

[6] R. H. Tale, G. K. Toradmal, V. B. Gopula. A practical and general ipso iodination of arylboronic acids using N-iodomorpholinium iodide (NIMI) as a novel iodinating agent: mild and regioselective synthesis of aryliodides. RSC Advances. 2015, 5 (103): 84910–84919 [2020-10-21]. ISSN 2046-2069. doi:10.1039/C5RA18820B （英语）.

[7] Hsing-Ying Chen, Wei-Te Peng, Ying-Hsien Lee, Yu-Lun Chang, Yen-Jen Chen, Yi-Chun Lai, Nai-Yuan Jheng, Hsuan-Ying Chen. Use of Base Control To Provide High Selectivity between Diaryl Thioether and Diaryl Disulfide for C–S Coupling Reactions of Aryl Halides and Sulfur and a Mechanistic Study. Organometallics. 2013-10-14, 32 (19): 5514–5522 [2020-10-21]. ISSN 0276-7333. doi:10.1021/om400784w （英语）.

[8] Bumagin, N. A.; Andryukhova, N. P.; Beletskaya, I. P. Catalyst for cross-coupling of vinylmagnesium bromide with aryl iodides（俄文）. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987. 7: 1681-1682. ISSN: 0002-3353.

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