1-碘丁烷
化合物
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。
1-碘丁烷[1] | |||
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IUPAC名 1-Iodobutane[2] | |||
别名 | 碘代正丁烷 正丁基碘 | ||
识别 | |||
CAS号 | 542-69-8 ![]() | ||
PubChem | 10962 | ||
ChemSpider | 10497 | ||
SMILES |
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Beilstein | 1420755 | ||
UN编号 | 1993 | ||
EINECS | 208-824-4 | ||
RTECS | EK4400000 | ||
MeSH | 1-iodobutane | ||
性质 | |||
化学式 | C4H9I | ||
摩尔质量 | 184.02 g·mol−1 | ||
外观 | 无色液体 | ||
密度 | 1.6171 g·cm−3[3] | ||
熔点 | −103.0 °C(170.2 K)[4] | ||
沸点 | 130.5 °C(403.6 K)[4] 39 °C(312 K)(23 Torr)[5] | ||
kH | 630 nmol Pa−1 kg−1 | ||
折光度n D |
1.5003(20 °C,589.3 nm)[6] | ||
危险性 | |||
GHS危险性符号![]() ![]() | |||
GHS提示词 | 危险 | ||
H-术语 | H226, H331 | ||
P-术语 | P261, P311 | ||
闪点 | 33 °C(306 K) | ||
相关物质 | |||
相关化学品 | 1-氟丁烷 1-氯丁烷 1-溴丁烷 | ||
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。 |
制备
编辑1-丁醇和红磷、碘反应[8],或和其它碘化试剂(如氢碘酸[9]、三苯基膦-碘[10]、亚磷酸三苯酯-碘[11]、1-碘-N,N,2-三甲基丙烯胺[12])反应,都可以得到1-碘丁烷。
反应
编辑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[13];和苯硫酚反应,得到苯基正丁基硫醚[14];和苯乙炔基锂反应,得到己炔基苯[15]。
它和镁在乙醚中回流,得到格氏试剂正丁基碘化镁[17];和锌在四氢呋喃中发生类似反应,得到正丁基碘化锌。[18]
参考文献
编辑- ^ Merck Index, 13th Edition, 1572.
- ^ 1-iodobutane - Compound Summary. PubChem Compound. USA: National Center for Biotechnology Information. 2005-03-26 [2012-03-04]. (原始内容存档于2012-10-11).
- ^ van de Walle, H.; de Landsberg, V. Preparation of symmetrical bromoiodoethylene. Bulletin des Societes Chimiques Belges, 1930. 39. 309-330. ISSN: 0037-9646.
- ^ 4.0 4.1 Timmermans, J. The melting point of organic substances. X. Bulletin des Societes Chimiques Belges, 1927. 36. 502-518. ISSN: 0037-9646.
- ^ 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.
- ^ Franzen, Volker. Exchange of chlorine or bromine for iodine in aliphatic and aromatic compounds. Chemische Berichte, 1954. 87. 1148-1154. ISSN: 0009-2940.
- ^ Joachim Buddrus, Bernd Schmidt, [《1-碘丁烷》在Google Books的內容。 Grundlagen der Organischen Chemie], Walter de Gruyter GmbH & Co KG. 2015: pp. 250, (德文)
- ^ 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.
- ^ 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
- ^ 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
- ^ 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.
- ^ 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.
- ^ Nagashima, Masumi; Kawahara, Takeo. Preparation of imidazolium iodides. 2002. JP 2002145864 A.
- ^ 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.
- ^ 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
- ^ 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.
- ^ 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.
- ^ 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.