查看“︁1-碘丁烷”︁的源代码

{{Chembox
| Watchedfields = changed
| verifiedrevid = 422161356
| Reference = <ref>''Merck Index'', 13th Edition, '''1572'''.</ref>
| ImageFile = butyl iodide.png
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 100
| ImageFileL1 = Butyl-iodide-3D-balls.png
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageNameL1 = Ball and stick model of butyl iodide
| ImageFileR1 = Butyl-iodide-3D-vdW.png
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageNameR1 = Butyl iodide
| IUPACName = 1-Iodobutane<ref>{{Cite web|title=1-iodobutane - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=10962|work=PubChem Compound|publisher=National Center for Biotechnology Information|accessdate=2012-03-04|location=USA|date=2005-03-26|archive-date=2012-10-11|archive-url=https://web.archive.org/web/20121011050918/http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=10962|dead-url=no}}</ref>
| OtherNames = 碘代正丁烷<br>正丁基碘
|Section1={{Chembox Identifiers
| CASNo = 542-69-8
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 607A6CC46R
| PubChem = 10962
| ChemSpiderID = 10497
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 208-824-4
| UNNumber = 1993
| MeSHName = 1-iodobutane
| RTECS = EK4400000
| Beilstein = 1420755
| SMILES = CCCCI
| StdInChI = 1S/C4H9I/c1-2-3-4-5/h2-4H2,1H3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KMGBZBJJOKUPIA-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
| C = 4
| H = 9
| I = 1
| Appearance = 无色液体
| Density = 1.6171 g·cm<sup>−3</sup><ref>van de Walle, H.; de Landsberg, V. Preparation of symmetrical bromoiodoethylene. ''Bulletin des Societes Chimiques Belges'', 1930. 39. 309-330. ISSN: 0037-9646.</ref>
| MeltingPt = {{convert|−103.0|C|K}}<ref name=Timmermans>Timmermans, J. The melting point of organic substances. X. ''Bulletin des Societes Chimiques Belges'', 1927. 36. 502-518. ISSN: 0037-9646.</ref>
| BoilingPt = {{convert|130.5|C|K}}<ref name=Timmermans /><br>{{convert|39|C|K}}（23 Torr）<ref>Amriev, R. A.; Velichko, F. K.; Bondarenko, O. P.; Freidlina, R. Kh. Reactions of organoiodide compounds, initiated by iron pentacarbonyl. ''Doklady Akademii Nauk SSSR'', 1985. 284 (1): 136-140. ISSN: 0002-3264.</ref>
| HenryConstant = 630 nmol Pa<sup>−1</sup> kg<sup>−1</sup>
| RefractIndex = 1.5003（20 °C，589.3 nm）<ref>Franzen, Volker. Exchange of chlorine or bromine for iodine in aliphatic and aromatic compounds. ''Chemische Berichte'', 1954. 87. 1148-1154. ISSN: 0009-2940.</ref>
}}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS flame}} {{GHS skull and crossbones}}
| GHSSignalWord = '''危险'''
| HPhrases = {{H-phrases|226|331}}
| PPhrases = {{P-phrases|261|311}}
| FlashPt = {{convert|33|C|K}}
}}
|Section4={{Chembox Related
| OtherCpds = {{link-de|1-氟丁烷|1-Fluorbutan}}<br>[[1-氯丁烷]]<br>[[1-溴丁烷]]
}}
}}

'''1-碘丁烷'''是一种[[有机化合物]]，化学式为C<sub>4</sub>H<sub>9</sub>I，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。<ref>{{Literatur| Autor=Joachim Buddrus, Bernd Schmidt | Titel=Grundlagen der Organischen Chemie  | Verlag=Walter de Gruyter GmbH & Co KG | ISBN=978-3-11-033105-9 | Jahr=2015 | Online={{Google Buch | BuchID=5Sh1BgAAQBAJ | Seite=250 }} | Seiten=250 }}</ref>
:<math>\mathrm{NaI + C_4H_9Br \longrightarrow C_4H_9I + NaBr}</math>
[[1-丁醇]]和红磷、碘反应<ref>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.</ref>，或和其它碘化试剂（如[[氢碘酸]]<ref>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</ref>、[[三苯基膦]]-[[碘]]<ref>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</ref>、[[亚磷酸三苯酯]]-碘<ref>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.</ref>、1-碘-''N'',''N'',2-三甲基丙烯胺<!-- CAS号：65560-41-0 --><ref>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.</ref>）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<ref>Nagashima, Masumi; Kawahara, Takeo. Preparation of imidazolium iodides. 2002. JP 2002145864 A.</ref>；和[[苯硫酚]]反应，得到苯基正丁基硫醚<ref>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.</ref>；和苯乙炔基锂反应，得到己炔基苯<ref>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</ref>。

它和[[硫氰酸钾]]在乙醇中回流反应，得到硫氰酸丁酯。<ref>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.</ref>
:<math>\mathrm{C_4H_9Br + KSCN \longrightarrow C_4H_9SCN + KI}</math>
它和[[镁]]在[[乙醚]]中回流，得到[[格氏试剂]]正丁基碘化镁<ref>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.</ref>；和[[锌]]在[[四氢呋喃]]中发生类似反应，得到正丁基碘化锌<!-- CAS号：34219-54-0 -->。<ref>Fleckenstein, Julia E.; Koszinowski, Konrad. Lithium organozincate complexes LiRZnX<sub>2</sub>: common species in organozinc chemistry. ''Organometallics'', 2011. 30 (18): 5018-5026. ISSN: 0276-7333. DOI: 10.1021/om200637s.</ref>
:<math>\mathrm{C_4H_9I + Mg \longrightarrow C_4H_9MgI}</math>
:<math>\mathrm{C_4H_9I + Zn \longrightarrow C_4H_9ZnI}</math>

==参考文献==
{{Reflist|2}}

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