3-硝基氯苯是一种有机化合物,化学式为C6H4ClNO2[1]

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  checkY
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 难溶
溶解性乙醚、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。

合成

编辑

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N-氯代丁二酰亚胺乙腈中加热反应制得;[2][3]3-氯苯胺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-氯苯甲酸氟硼酸硝酰反应,也能得到产物。[5]

反应

编辑

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

编辑
  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).