3-硝基氯苯

3-硝基氯苯
	IUPAC名; 1-Chloro-3-nitrobenzene
别名	m-Nitrochlorobenzene; m-Chloronitrobenzene; 3-Chloronitrobenzene
识别
CAS号	121-73-3
PubChem	8489
ChemSpider	21106013
SMILES	C1=CC(=CC(=C1)Cl)[N+](=O)[O-];
InChI	1/C6H4ClNO2/c7-5-2-1-3-6(4-5)8(9)10/h1-4H;
InChIKey	KMAQZIILEGKYQZ-UHFFFAOYAS
EINECS	204-496-1
性质
化学式	C6H4ClNO2
摩尔质量	157.55 g·mol−1
外观	浅黄色晶体
密度	1.534 g/mL
熔点	43—47 °C（316—320 K）
沸点	236 °C（509 K）
溶解性（水）	难溶
溶解性（苯、乙醚、热乙醇、丙酮）	可溶
危险性
主要危害	有毒
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

3-硝基氯苯是一种有机化合物，化学式为C₆H₄ClNO₂。^[1]

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合成

氯苯的直接硝化反应主要得到2-位（邻位）和4-位（对位）取代的产物，通常以其它方法制备3-硝基氯苯。文献报道了不同的制备方法，例如，它可由3-硝基苯硼酸和N-氯代丁二酰亚胺在乙腈中加热反应制得；^[2]^[3]3-氯苯胺和3-氯过氧苯甲酸的氧化反应，可以得到3-硝基氯苯；^[4]或者3-氯苯甲酸和氟硼酸硝酰反应，也能得到产物。^[5]

反应

3-硝基氯苯的反应可以发生在硝基或氯上。例如，它可被还原为3-氯苯胺^[6]^[7]，和芳基硼酸发生偶联反应^[8]等。

参考文献

[1]
Gerald Booth. Nitro Compounds, Aromatic. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2007. ISBN 978-3527306732. doi:10.1002/14356007.a17_411.
[2]
Wen He, Rongli Zhang, Mingzhong Cai. A highly efficient heterogeneous copper-catalyzed chlorodeboronation of arylboronic acids leading to chlorinated arenes. RSC Advances. 2017, 7 (2): 764–770 [2021-05-18]. ISSN 2046-2069. doi:10.1039/C6RA25666J （英语）.
[3]
Hong Wu, John Hynes. Copper-Catalyzed Chlorination of Functionalized Arylboronic Acids. Organic Letters. 2010-03-19, 12 (6): 1192–1195 [2021-05-18]. ISSN 1523-7060. doi:10.1021/ol9029337 （英语）.
[4]
Jia Liu, Jue Li, Jiangmeng Ren, Bu-Bing Zeng. Oxidation of aromatic amines into nitroarenes with m-CPBA. Tetrahedron Letters. 2014-02, 55 (9): 1581–1584 [2021-05-18]. doi:10.1016/j.tetlet.2014.01.073. （原始内容存档于2018-06-10）（英语）.
[5]
Palani Natarajan, Renu Chaudhary, Paloth Venugopalan. Silver(I)-Promoted ipso -Nitration of Carboxylic Acids by Nitronium Tetrafluoroborate. The Journal of Organic Chemistry. 2015-11-06, 80 (21): 10498–10504 [2021-05-18]. ISSN 0022-3263. doi:10.1021/acs.joc.5b02133. （原始内容存档于2020-06-17）（英语）.
[6]
Jing Lv, Zhengtang Liu, Zhengping Dong. Iron oxide modified N-doped porous carbon derived from porous organic polymers as a highly-efficient catalyst for reduction of nitroarenes. Molecular Catalysis. 2020-12, 498: 111249 [2021-05-18]. doi:10.1016/j.mcat.2020.111249 （英语）.
[7]
Donatella Giomi, Jacopo Ceccarelli, Antonella Salvini, Alberto Brandi. Organocatalytic Reduction of Nitroarenes with Phenyl(2‐quinolyl)methanol. ChemistrySelect. 2020-09-14, 5 (34): 10511–10515 [2021-05-18]. ISSN 2365-6549. doi:10.1002/slct.202003234 （英语）.
[8]
Hamid Azizollahi, Hossein Eshghi, José‐Antonio García‐López. Fe 3 O 4 ‐SAHPG‐Pd 0 nanoparticles: A ligand‐free and low Pd loading quasiheterogeneous catalyst active for mild Suzuki–Miyaura coupling and CH activation of pyrimidine cores. Applied Organometallic Chemistry. 2021-01, 35 (1) [2021-05-18]. ISSN 0268-2605. doi:10.1002/aoc.6020 （英语）.

[Ullmann-1] [1]
Gerald Booth. Nitro Compounds, Aromatic. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2007. ISBN 978-3527306732. doi:10.1002/14356007.a17_411.

[2] [2]
Wen He, Rongli Zhang, Mingzhong Cai. A highly efficient heterogeneous copper-catalyzed chlorodeboronation of arylboronic acids leading to chlorinated arenes. RSC Advances. 2017, 7 (2): 764–770 [2021-05-18]. ISSN 2046-2069. doi:10.1039/C6RA25666J （英语）.

[3] [3]
Hong Wu, John Hynes. Copper-Catalyzed Chlorination of Functionalized Arylboronic Acids. Organic Letters. 2010-03-19, 12 (6): 1192–1195 [2021-05-18]. ISSN 1523-7060. doi:10.1021/ol9029337 （英语）.

[4] [4]
Jia Liu, Jue Li, Jiangmeng Ren, Bu-Bing Zeng. Oxidation of aromatic amines into nitroarenes with m-CPBA. Tetrahedron Letters. 2014-02, 55 (9): 1581–1584 [2021-05-18]. doi:10.1016/j.tetlet.2014.01.073. （原始内容存档于2018-06-10）（英语）.

[5] [5]
Palani Natarajan, Renu Chaudhary, Paloth Venugopalan. Silver(I)-Promoted ipso -Nitration of Carboxylic Acids by Nitronium Tetrafluoroborate. The Journal of Organic Chemistry. 2015-11-06, 80 (21): 10498–10504 [2021-05-18]. ISSN 0022-3263. doi:10.1021/acs.joc.5b02133. （原始内容存档于2020-06-17）（英语）.

[6] [6]
Jing Lv, Zhengtang Liu, Zhengping Dong. Iron oxide modified N-doped porous carbon derived from porous organic polymers as a highly-efficient catalyst for reduction of nitroarenes. Molecular Catalysis. 2020-12, 498: 111249 [2021-05-18]. doi:10.1016/j.mcat.2020.111249 （英语）.

[7] [7]
Donatella Giomi, Jacopo Ceccarelli, Antonella Salvini, Alberto Brandi. Organocatalytic Reduction of Nitroarenes with Phenyl(2‐quinolyl)methanol. ChemistrySelect. 2020-09-14, 5 (34): 10511–10515 [2021-05-18]. ISSN 2365-6549. doi:10.1002/slct.202003234 （英语）.

[8] [8]
Hamid Azizollahi, Hossein Eshghi, José‐Antonio García‐López. Fe 3 O 4 ‐SAHPG‐Pd 0 nanoparticles: A ligand‐free and low Pd loading quasiheterogeneous catalyst active for mild Suzuki–Miyaura coupling and CH activation of pyrimidine cores. Applied Organometallic Chemistry. 2021-01, 35 (1) [2021-05-18]. ISSN 0268-2605. doi:10.1002/aoc.6020 （英语）.

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