1-氯-4-溴丁烷

1-氯-4-溴丁烷
別名	1-溴-4-氯丁烷
識別
CAS號	6940-78-9
性質
化學式	C4H8BrCl
摩爾質量	171.46 g·mol−1
密度	1.488 g·cm−3（20 °C）
沸點	175 °C
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

1-氯-4-溴丁烷是一種有機化合物，屬鹵代烴，化學式為C₄H₈BrCl。

製備

1-氯-4-溴丁烷有多種製備方式，如四氫呋喃和鹽酸反應，得到4-氯-1-丁醇，再對其進行溴化得到。^[3]類似的方法還有乙酸-4-氯丁酯和氫溴酸的反應。^[4]1,4-二氯丁烷和1,4-二溴丁烷進行鹵素交換，也可以得到該化合物。^[5]

性質

1-氯-4-溴丁烷和疊氮化鈉在DMF中反應，可以得到1-疊氮基-4-氯丁烷。^[6]它在碳酸鉀的存在下和苯酚在DMF中加熱反應，得到(4-氯丁氧基)苯；^[7]通過類似的反應，也可製得(4-氯丁基)(苯基)硫醚。^[8]

參考文獻

^ 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 （英語）.
^ 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 （英語）.
^ Servigne, Marcel; Szarvasi, Etienne; Neuvy, Liliane. New method of preparation of 1-bromo-4-chlorobutane. Compt. rend., 1955. 241: 963-964.
^ Normant, Henri; Voreux, Gerard. Preparation and properties of ω-halogenated valeronitriles. Compt. rend., 1950. 231: 703-704.
^ 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 （英語）.
^ 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. （原始內容存檔於2018-06-04）（英語）.
^ 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.
^ 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 （英語）.

[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 （英語）.

[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 （英語）.

[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 （英語）.

[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. （原始內容存檔於2018-06-04）（英語）.

[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 （英語）.

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