1-碘丁烷

1-碘丁烷
Ball and stick model of butyl iodide	Butyl iodide
	IUPAC名; 1-Iodobutane
別名	碘代正丁烷; 正丁基碘
識別
CAS號	542-69-8
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
熔點	−103.0 °C（170.2 K）
沸點	130.5 °C（403.6 K）; 39 °C（312 K）（23 Torr）
kH	630 nmol Pa−1 kg−1
折光度n; D	1.5003（20 °C，589.3 nm）
危險性
	GHS危險性符號;
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。

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。

製備

1-碘丁烷可由1-溴丁烷和碘化鈉反應得到。^[7]

\mathrm {NaI+C_{4}H_{9}Br\longrightarrow C_{4}H_{9}I+NaBr}

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-碘^[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

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]

\mathrm {C_{4}H_{9}Br+KSCN\longrightarrow C_{4}H_{9}SCN+KI}

它和鎂在乙醚中回流，得到格氏試劑正丁基碘化鎂^[17]；和鋅在四氫呋喃中發生類似反應，得到正丁基碘化鋅。^[18]

\mathrm {C_{4}H_{9}I+Mg\longrightarrow C_{4}H_{9}MgI}

\mathrm {C_{4}H_{9}I+Zn\longrightarrow C_{4}H_{9}ZnI}

參考文獻

^ Merck Index, 13th Edition, 1572.
^ 1-iodobutane - Compound Summary. PubChem Compound. USA: National Center for Biotechnology Information. 2005-03-26 [2012-03-04]. （原始內容存檔於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,
ISBN 978-3-11-033105-9
（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.

[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.

[Timmermans-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,
ISBN 978-3-11-033105-9
（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.

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