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1-氯-4-溴丁烷

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维基百科，自由的百科全书
1-氯-4-溴丁烷
别名 1-溴-4-氯丁烷
识别
CAS号 6940-78-9  checkY
性质
化学式 C4H8BrCl
摩尔质量 171.46 g·mol−1
密度 1.488 g·cm−3（20 °C）[1]
沸点 175 °C[2]
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

1-氯-4-溴丁烷是一种有机化合物，属卤代烃，化学式为C4H8BrCl。

制备

1-氯-4-溴丁烷有多种制备方式，如四氢呋喃和盐酸反应，得到4-氯-1-丁醇，再对其进行溴化得到。[3]类似的方法还有乙酸-4-氯丁酯和氢溴酸的反应。[4]1,4-二氯丁烷和1,4-二溴丁烷进行卤素交换，也可以得到该化合物。[5]

性质

1-氯-4-溴丁烷和叠氮化钠在DMF中反应，可以得到1-叠氮基-4-氯丁烷。[6]它在碳酸钾的存在下和苯酚在DMF中加热反应，得到(4-氯丁氧基)苯；[7]通过类似的反应，也可制得(4-氯丁基)(苯基)硫醚。[8]

参考文献

  1. ^ Donald Starr, R. M. Hixon. Reduction of Furan and the Preparation of Tetramethylene Derivatives. Journal of the American Chemical Society. 1934-07, 56 (7): 1595–1596 [2020-05-29]. ISSN 0002-7863. doi:10.1021/ja01322a041 （英语）. 
  2. ^ Gordon G. Cash, Suzanne Hartigan, Jay Tunkel. Normal boiling points of haloalkanes from electrotopological state indices. Toxicological & Environmental Chemistry. 2008-11, 90 (6): 1073–1089 [2020-05-29]. ISSN 0277-2248. doi:10.1080/02772240701862116 （英语）. 
  3. ^ Servigne, Marcel; Szarvasi, Etienne; Neuvy, Liliane. New method of preparation of 1-bromo-4-chlorobutane. Compt. rend., 1955. 241: 963-964.
  4. ^ Normant, Henri; Voreux, Gerard. Preparation and properties of ω-halogenated valeronitriles. Compt. rend., 1950. 231: 703-704.
  5. ^ Roger C. Hahn. Homogeneous nucleophile exchange. 1. Simple, high-yield synthesis of some heterodihalides. The Journal of Organic Chemistry. 1988-03, 53 (6): 1331–1333 [2020-05-29]. ISSN 0022-3263. doi:10.1021/jo00241a045 （英语）. 
  6. ^ Monica Piras, Alexandra Andriu, Andrea Testa, Paul Wienecke, Ian Fleming, Matteo Zanda. Design and Synthesis of an RGD Peptidomimetic-Paclitaxel Conjugate Targeting αvβ3 Integrin for Tumour-Directed Drug Delivery. Synlett. 2017-12, 28 (20): 2769–2776 [2020-05-29]. ISSN 0936-5214. doi:10.1055/s-0036-1590898. （原始内容存档于2018-06-04） （英语）. 
  7. ^ Ammenn, Jochen; Gillig, James Ronald; Heinz, Lawrence Joseph; Hipskind, Philip Arthur; Kinnick, Michael Dean; Lai, Yen-shi; Morin, John Michael, Jr.; Nixon, James Arthur; Ott, Carsten; Savin, Kenneth Allen; Schotten, Theo; Slieker, Lawrence John; Snyder, Nancy June; Robertson, Michael Alan. Preparation of 1,3,4-oxadiazoles and related compounds for use as melanin concentrating hormone antagonists in the treatment of obesity and diabetes. 2003. WO 2003097047 A1.
  8. ^ Alissa Horn, Patrick H. Dussault. Synthesis of α-Cyano and α-Sulfonyl Cyclic Ethers via Intramolecular Reactions of Peroxides with Sulfone- and Nitrile-Stabilized Carbanions. The Journal of Organic Chemistry. 2019-11-15, 84 (22): 14611–14626 [2020-05-29]. ISSN 0022-3263. doi:10.1021/acs.joc.9b02112 （英语）. 
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