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。[6]

2-溴丙烷
Ball and stick model of 2-bromopropane
Spacefill model of 2-bromopropane
IUPAC名
2-Bromopropane[1]
别名 异丙基溴、對溴丙烷[2]
识别
CAS号 75-26-3  checkY
PubChem 6358
ChemSpider 6118
SMILES
 
  • CC(C)Br
Beilstein 741852
UN编号 2344
EINECS 200-855-1
RTECS TX4111000
MeSH 2-bromopropane
性质
化学式 C3H7Br
摩尔质量 122.99 g·mol−1
外观 无色液体
密度 1.32 g·cm−3（15 °C）[3]
1.31 g·cm−3（20 °C）[4]
熔点 −89 °C（184 K）[5]
沸点 59.5 °C（332.6 K）[5]
溶解性（水） 3.2 g L−1 (at 20 °C)
log P 2.136
蒸氣壓 32 kPa（20 °C）
kH 1.0 μmol·Pa−1·mol−1
折光度n
D		 1.4251（20 °C，589.3 nm）[4]
黏度 0.4894 mPa·s（20 °C）
热力学
ΔfHm⦵298K −129 kJ mol−1
ΔcHm⦵ −2.0537–−2.0501 MJ mol−1
热容 135.6 J K mol−1
危险性
GHS危险性符号
《全球化学品统一分类和标签制度》（简称“GHS”）中易燃物的标签图案 《全球化学品统一分类和标签制度》（简称“GHS”）中对人体有害物质的标签图案
GHS提示词 危险
H-术语 H225, H360, H373
P-术语 P210, P308+313
NFPA 704
3
2
0
 
相关物质
相关化合物
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

制备

2-溴丙烷可由丙烯和溴化氢发生亲电加成反应得到：[7]

异丙醇和溴化试剂（如硫酸-溴化钠[8]、磷-溴[9]、三溴化磷[10]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；[11]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[12]。

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；[13]它和硫氰酸钠发生类似反应，生成硫氰酸异丙酯。[14]它也可以和一氟化氯反应，生成2-氟丙烷。[15]

参考文献
  1. . PubChem Compound. USA: National Center for Biotechnology Information. Identification. 27 March 2005 [15 June 2012]. （原始内容存档于2013-12-14）.
  2. Wilfred L.F. Armarego and Christina Li Lin Chai, Purification of laboratory chemicals, 7th edition, Butterworth-Heinemann, 2013, p. 176 （页面存档备份，存于）
  3. Timmermans, J.; Martin, F. The work of the International Bureau of Physical-Chemical Standards. III. Study of the physical constants of twenty organic compounds. Journal de Chimie Physique et de Physico-Chimie Biologique, 1928. 25. 411-451. ISSN: 0021-7689.
  4. Afenkov, N. I. Measurement of the specific volumes of a few organic liquids with the help of the sectional dilatometer. Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya, 1958. 6. 128-132. ISSN: 0579-2991.
  5. "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2020-07-12]
  6. . WHO. 2023-12-01 [2023-12-06].
  7. 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.
  8. 王玉凤, 王江. 2–溴丙烷合成的研究. 黑龙江日化, 1998, (4): 4-6.
  9. 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.
  10. 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.
  11. Treu, Matthias. Synthesis of Novel Galanthamine Analog Acetylcholinesterase Inhibitors via Tandem Cyclization [Dissertation]. 2000. Vienna University of Technology.
  12. 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.
  13. Textbook of Practical Organic Chemistry, 5th Edition, Prentice Hall, 1989
  14. Shriner, R. L. Isopropyl thiocyanate. Organic Syntheses, 1931. XI. 92-93. ISSN: 0078-6209. DOI: 10.15227/orgsyn.011.0092.
  15. 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.
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