1-碘丁烷

化合物

1-碘丁烷是一種有機化合物,化學式為C4H9I,它是丁烷的甲基氫被碘取代的產物。

1-碘丁烷[1]
Ball and stick model of butyl iodide
Butyl iodide
IUPAC名
1-Iodobutane[2]
別名 碘代正丁烷
正丁基碘
識別
CAS號 542-69-8  checkY
PubChem 10962
ChemSpider 10497
SMILES
 
  • CCCCI
Beilstein 1420755
UN編號 1993
EINECS 208-824-4
RTECS EK4400000
MeSH 1-iodobutane
性質
化學式 C4H9I
摩爾質量 184.02 g·mol−1
外觀 無色液體
密度 1.6171 g·cm−3[3]
熔點 −103.0 °C(170.2 K)[4]
沸點 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]
危險性
GHS危險性符號
《全球化學品統一分類和標籤制度》(簡稱「GHS」)中易燃物的標籤圖案 《全球化學品統一分類和標籤制度》(簡稱「GHS」)中有毒物質的標籤圖案
GHS提示詞 危險
H-術語 H226, H331
P-術語 P261, P311
閃點 33 °C(306 K)
相關物質
相關化學品 1-氟丁烷德語1-Fluorbutan
1-氯丁烷
1-溴丁烷
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

製備

編輯

1-碘丁烷可由1-溴丁烷碘化鈉反應得到。[7]

 

1-丁醇和紅磷、碘反應[8],或和其它碘化試劑(如氫碘酸[9]三苯基膦-[10]亞磷酸三苯酯-碘[11]、1-碘-N,N,2-三甲基丙烯胺[12])反應,都可以得到1-碘丁烷。

反應

編輯

1-碘丁烷是一種烷基化試劑,經過反應可以得到含有丁基的化合物,如和咪唑類化合物反應,得到咪唑鎓鹽[13];和苯硫酚反應,得到苯基正丁基硫醚[14];和苯乙炔基鋰反應,得到己炔基苯[15]

它和硫氰酸鉀在乙醇中回流反應,得到硫氰酸丁酯。[16]

 

它和乙醚中回流,得到格氏試劑正丁基碘化鎂[17];和四氫呋喃中發生類似反應,得到正丁基碘化鋅。[18]

 
 

參考文獻

編輯
  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]. (原始內容存檔於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.