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1-碘丁烷

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1-碘丁烷[1]
Ball and stick model of butyl iodide
Butyl iodide
IUPAC名
1-Iodobutane[2]
别名 碘代正丁烷
正丁基碘
识别
CAS号 542-69-8  checkY
PubChem 10962
ChemSpider 10497
SMILES
 
  • CCCCI
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
《全球化学品统一分类和标签制度》(简称“GHS”)中易燃物的标签图案 《全球化学品统一分类和标签制度》(简称“GHS”)中有毒物质的标签图案
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-氟丁烷德语1-Fluorbutan
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。

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-溴丁烷碘化钠反应得到。[7]

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-[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

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]

它和硫氰酸钾在乙醇中回流反应,得到硫氰酸丁酯。[16]

它和乙醚中回流,得到格氏试剂正丁基碘化镁[17];和四氢呋喃中发生类似反应,得到正丁基碘化锌。[18]

参考文献

  1. ^ Merck Index, 13th Edition, 1572.
  2. ^ 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). 
  3. ^ van de Walle, H.; de Landsberg, V. Preparation of symmetrical bromoiodoethylene. Bulletin des Societes Chimiques Belges, 1930. 39. 309-330. ISSN: 0037-9646.
  4. ^ 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.
  5. ^ 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.
  6. ^ Franzen, Volker. Exchange of chlorine or bromine for iodine in aliphatic and aromatic compounds. Chemische Berichte, 1954. 87. 1148-1154. ISSN: 0009-2940.
  7. ^ 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) 
  8. ^ 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.
  9. ^ 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
  10. ^ 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
  11. ^ 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.
  12. ^ 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.
  13. ^ Nagashima, Masumi; Kawahara, Takeo. Preparation of imidazolium iodides. 2002. JP 2002145864 A.
  14. ^ 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.
  15. ^ 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
  16. ^ 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.
  17. ^ 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.
  18. ^ 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.