2-溴丙烷

2-溴丙烷是一种有机化合物，化学式为C3H7Br，是丙烷的亚甲基氢被溴取代的产物。它的同分异构体是1-溴丙烷。它在2023年被列入IARC第2A类致癌物质。

制备
2-溴丙烷可由丙烯和溴化氢发生亲电加成反应得到：Griesbaum, Karl; Mach, Helmut. Crossover products from joint reactions of alkenes and alkynes with hydrogen halides. Chemische Berichte, 1982. 115 (12): 3818-3829. ISSN: 0009-2940.
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异丙醇和溴化试剂（如硫酸-溴化钠王玉凤, 王江. 2–溴丙烷合成的研究. 黑龙江日化, 1998, (4): 4-6.、磷-溴Goshorn, R. H.; Boyd, Thomas; Degering, E. F. Alkyl and alkylene bromides. II. Phosphorus and bromine method. Organic Syntheses, 1941. 1 (2). 36-41. ISSN: 0078-6209.、三溴化磷Mundy, Bradford P.; Stewart, Catherine A. Phosphorus(III) bromide. e-EROS Encyclopedia of Reagents for Organic Synthesis, 2008. pp 1-4. ISBN 978-0-470-84289-8.等）发生溴化反应，也能得到2-溴丙烷。

反应
2-溴丙烷可以用于合成异丙基化合物，例如在碳酸钾的存在下，2-溴丙烷和4-羟基苯甲醛在乙腈中反应，可以得到4-异丙氧基苯甲醛；Treu, Matthias. Synthesis of Novel Galanthamine Analog Acetylcholinesterase Inhibitors via Tandem Cyclization [Dissertation]. 2000. Vienna University of Technology.碳酸铯作为碱、四(三苯基膦)钯作为催化剂，它和呋喃-2-硼酸反应，得到2-异丙基呋喃Li, Jiuyi; Lu, Lin; Pan, Qi; Ren, Yanwei; Liu, Bo; Yin, Biaolin. Palladium-Catalyzed Dearomatizing Alkoxydiarylation of Furan Rings by Coupling with Arylboronic Acids: Access to Polysubstituted Oxabicyclic Compounds. Advanced Synthesis & Catalysis, 2017. 359 (11): 2001-2007. ISSN: 1615-4150. DOI: 10.1002/adsc.201601437.。

它可以和碘化钠在丙酮中发生卤素交换反应，生成2-碘丙烷；Textbook of Practical Organic Chemistry, 5th Edition, Prentice Hall, 1989它和硫氰酸钠发生类似反应，生成硫氰酸异丙酯。Shriner, R. L. Isopropyl thiocyanate. Organic Syntheses, 1931. XI. 92-93. ISSN: 0078-6209. DOI: 10.15227/orgsyn.011.0092.它也可以和一氟化氯反应，生成2-氟丙烷。Morozova, T. V.; Chuvatkin, N. N.; Panteleeva, I. Yu.; Boguslavskaya, L. S. Reactions of chlorine monofluoride. IV. Relative rates of the substitutive fluorination of bromo-substituted alkanes. Hydride and other migrations during fluorination. Zhurnal Organicheskoi Khimii, 1984. 20 (7): 1379-1388. ISSN: 0514-7492.

参考文献

Category:溴代烷烃
Category:卤代丙烷
Category:IARC第2A类致癌物质