4-甲基苯胺

4-甲基苯胺是有机化合物，化学式C₇H₉N，是甲苯胺的同分异构体。

4-甲基苯胺
别名	对甲基苯胺
识别
CAS号	106-49-0  Y
PubChem	7813
性质
化学式	C7H9N
摩尔质量	107.15 g·mol−1
密度	1.046 g·cm−3[1]
熔点	44—45 °C（317—318 K）[1]
沸点	200.4 °C（473.5 K）[1]
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

合成

4-甲基苯胺可由氢气^[2]、水合肼^[3]、硼氢化钠^[4]、铝汞齐^[5]等还原剂还原4-硝基甲苯得到。

反应

氨基的反应

4-甲基苯胺可以和酰卤或酸酐反应得到相应酰胺，如和对甲苯磺酰氯反应，得到N-(对甲苯基)对甲苯磺酰胺^[6]；和乙酸酐反应，得到N-对甲基苯基乙酰胺；^[7]和酸或卤代烃反应，得到4-甲基苯铵盐或相应的季铵盐；^[8]和醛反应，生成氮－碳偶联的产物，如：^[9]

苯环的取代反应

和N-溴代丁二酰亚胺反应得到2-溴-4-甲基苯胺；^[10]碘和二甲基亚砜存在时和4-氟苯硫酚在二甲基甲酰胺反应，可得到取代氨基邻位的产物2-(4-氟苯硫基)-4-甲基苯胺；^[11]和甲醛反应生成Tröger氏碱。

参考文献

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3. Feng, Binbin; Xu, Qionghao; Wu, Xiaoxue; Ye, Chunlin; Fu, Yanghe; Chen, De-Li; Zhang, Fumin; Zhu, Weidong. MOF-derived N-doped carbon composites embedded with Fe/Fe3C nanoparticles as highly chemoselective and stable catalysts for catalytic transfer hydrogenation of nitroarenes. Applied Surface Science. 2021, 557: 149837. ISSN 0169-4332. doi:10.1016/j.apsusc.2021.149837 （英语）.
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6. MacKenzie, Ian A.; Wang, Leifeng; Onuska, Nicholas P. R.; Williams, Olivia F.; Begam, Khadiza; Moran, Andrew M.; Dunietz, Barry D.; Nicewicz, David A. Discovery and characterization of an acridine radical photoreductant. Nature. 2020, 580 (7801): 76–80. ISSN 0028-0836. doi:10.1038/s41586-020-2131-1 （英语）.
7. Govender, Hogantharanni; Mocktar, Chunderika; Koorbanally, Neil A. Synthesis and Bioactivity of Quinoline-3-carboxamide Derivatives. Journal of Heterocyclic Chemistry. 2018, 55 (4): 1002–1009. ISSN 0022-152X. doi:10.1002/jhet.3132 （英语）.
8. Balybin, Alexei G.; Panov, Yuri M.; Erkhova, Ludmila V.; Lemenovskii, Dmitry A.; Krut’ko, Dmitry P. Selective Hofmann alkylation of aromatic-aliphatic diamines in the presence of carbon dioxide. Mendeleev Communications. 2019, 29 (4): 438–440. ISSN 0959-9436. doi:10.1016/j.mencom.2019.07.028 （英语）.
9. Chen, Min-Hsien; Hsieh, Jen-Chieh; Lee, Yi-Hsien; Cheng, Chien-Hong. Controlled Synthesis of Enantioselective 1-Aminoindenes via Cobalt-Catalyzed [3 + 2] Annulation Reaction. ACS Catalysis. 2018, 8 (10): 9364–9369. ISSN 2155-5435. doi:10.1021/acscatal.8b02566 （英语）.
10. Appa, Rama Moorthy; Naidu, Bandameeda Ramesh; Lakshmidevi, Jangam; Vantikommu, Jyothi; Venkateswarlu, Katta. Added catalyst-free, versatile and environment beneficial bromination of (hetero)aromatics using NBS in WEPA. SN Applied Sciences. 2019, 1 (10). ISSN 2523-3963. doi:10.1007/s42452-019-1274-x （英语）.
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