1-碘丁烷

1-碘丁烷是一种有机化合物，化学式为C4H9I，它是丁烷的甲基氢被碘取代的产物。

制备
1-碘丁烷可由1-溴丁烷和碘化钠反应得到。

1-丁醇和红磷、碘反应Sulikowski, Gary A.; Sulikowski, Michelle M.; Haukaas, Michael H.; Moon, Bongjin. Iodomethane. e-EROS Encyclopedia of Reagents for Organic Synthesis. pp 1-10. ISBN 978-0-470-84289-8.，或和其它碘化试剂（如氢碘酸Klein, Suzane M.; Zhang, Cungen; Jiang, Yu Lin. Simple synthesis of fresh alkyl iodides using alcohols and hydriodic acid. Tetrahedron Letters, 2008. 49 (16): 2638-2641. ISSN: 0040-4039. DOI: 10.1016/j.tetlet.2008.02.106、三苯基膦-碘Hajipour, Abdol Reza; Mostafavi, Majid; Ruoho, Arnold E. Iodination of alcohols using triphenylphosphine/iodine in ionic liquid under solvent-free conditions. Organic Preparations and Procedures International, 2009. 41 (1): 87-91. ISSN: 0030-4948. DOI: 10.1080/00304940802711127、亚磷酸三苯酯-碘Castro, Bertrand R. Replacement of alcoholic hydroxyl groups by halogens and other nucleophiles via oxyphosphonium intermediates. Organic Reactions (Hoboken, NJ, United States), 1983. 29. DOI: 10.1002/0471264180.or029.01.、1-碘-N,N,2-三甲基丙烯胺Munyemana, Francois; Frisque-Hesbain, Anne Marie; Devos, Alain; Ghosez, Leon. Synthesis of alkyl halides under neutral conditions. Tetrahedron Letters, 1989. 30 (23): 3077-3080. ISSN: 0040-4039. DOI: 10.1016/S0040-4039(00)99407-3.）反应，都可以得到1-碘丁烷。

反应
1-碘丁烷是一种烷基化试剂，经过反应可以得到含有丁基的化合物，如和咪唑类化合物反应，得到咪唑鎓盐Nagashima, Masumi; Kawahara, Takeo. Preparation of imidazolium iodides. 2002. JP 2002145864 A.；和苯硫酚反应，得到苯基正丁基硫醚Vijaikumar, Sakthivel; Pitchumani, Kasi. Simple, solvent free syntheses of unsymmetrical sulfides from thiols and alkyl halides using hydrotalcite clays. Journal of Molecular Catalysis A: Chemical, 2004. 217 (1-2): 117-120. ISSN: 1381-1169. DOI: 10.1016/j.molcata.2004.03.002.；和苯乙炔基锂反应，得到己炔基苯Xu, Guoqiang; Li, Xiaoyan; Sun, Hongjian. Nickel-catalyzed cross-coupling of primary alkyl halides with phenylethynyl- and trimethylsilyethynyllithium reagents. Journal of Organometallic Chemistry, 2011. 696 (18): 3011-3014. ISSN: 0022-328X. DOI: 10.1016/j.jorganchem.2011.05.017。

它和硫氰酸钾在乙醇中回流反应，得到硫氰酸丁酯。Benfodda, Zohra; Guillen, Franck; Arnion, Helene; Dahmani, Abdelkader; Blancou, Hubert. A new synthesis of alkane and polyfluoroalkanesulfonyl chlorides. Heteroatom Chemistry, 2009. 20 (6): 355-361. ISSN: 1042-7163. DOI: 10.1002/hc.20559.

它和镁在乙醚中回流，得到格氏试剂正丁基碘化镁Kawasaki, Masashi; Shimizu, Momo; Kuroyanagi, Saki; Shishido, Yoshiaki; Komiyama, Tsuyoshi; Toyooka, Naoki. Syntheses and odor properties of optically active dimethyl octenone and its analogs. Tetrahedron: Asymmetry, 2016. 27 (6): 285-293. ISSN: 0957-4166. DOI:10.1016/j.tetasy.2016.02.002.；和锌在四氢呋喃中发生类似反应，得到正丁基碘化锌。Fleckenstein, Julia E.; Koszinowski, Konrad. Lithium organozincate complexes LiRZnX2: common species in organozinc chemistry. Organometallics, 2011. 30 (18): 5018-5026. ISSN: 0276-7333. DOI: 10.1021/om200637s.

参考文献

Category:烷基化试剂
Category:碘代烷烃
Category:正丁基化合物
Category:一卤丁烷