2-溴丙烷

2-溴丙烷
Ball and stick model of 2-bromopropane	Spacefill model of 2-bromopropane
	IUPAC名; 2-Bromopropane
别名	异丙基溴、对溴丙烷
识别
CAS号	75-26-3
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）; 1.31 g·cm−3（20 °C）
熔点	−89 °C（184 K）
沸点	59.5 °C（332.6 K）
溶解性（水）	3.2 g L−1 (at 20 °C)
log P	2.136
蒸气压	32 kPa（20 °C）
kH	1.0 μmol·Pa−1·mol−1
折光度n; D	1.4251（20 °C，589.3 nm）
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;
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	溴乙烷; 1-溴丙烷; 叔丁基溴; 1-溴丁烷; 2-溴丁烷;
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

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]

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（德语：2-Fluorpropan）。^[15]

参考文献

^ 2-bromopropane - Compound Summary. 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）.
^ 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，存于互联网档案馆）
^ 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.
^ ^4.0 ^4.1 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.
^ ^5.0 ^5.1 "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2020-07-12]
^ IARC MONOGRAPHS ON THE IDENTIFICATION OF CARCINOGENIC HAZARDS TO HUMANS. WHO. 2023-12-01 [2023-12-06]. （原始内容存档于2021-04-05）.
^ 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.
^ 王玉凤, 王江. 2–溴丙烷合成的研究. 黑龙江日化, 1998, (4): 4-6.
^ 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.
^ 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.
^ Treu, Matthias. Synthesis of Novel Galanthamine Analog Acetylcholinesterase Inhibitors via Tandem Cyclization [Dissertation]. 2000. Vienna University of Technology.
^ 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.
^ Textbook of Practical Organic Chemistry, 5th Edition, Prentice Hall, 1989
^ Shriner, R. L. Isopropyl thiocyanate. Organic Syntheses, 1931. XI. 92-93. ISSN: 0078-6209. DOI: 10.15227/orgsyn.011.0092.
^ 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.

[1] 2-bromopropane - Compound Summary. 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，存于互联网档案馆）

[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.

[Afenkov-4] 4.0 ^4.1 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.

[Phys-5] 5.0 ^5.1 "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2020-07-12]

[6] IARC MONOGRAPHS ON THE IDENTIFICATION OF CARCINOGENIC HAZARDS TO HUMANS. WHO. 2023-12-01 [2023-12-06]. （原始内容存档于2021-04-05）.

[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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