4-甲基苯胺

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

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。

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時和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]和甲醛反應生成Tröger氏鹼。

参考文献

^ ^1.0 ^1.1 ^1.2 "Hazardous Substances Data Bank" data were obtained from the National Library of Medicine (US). SciFinder. [2021-07-12]. （原始内容存档于2020-04-19）（英语）.
^ Tian, Shubo; Wang, Bingxue; Gong, Wanbing; He, Zizhan; Xu, Qi; Chen, Wenxing; Zhang, Qinghua; Zhu, Youqi; Yang, Jiarui; Fu, Qiang; Chen, Chun; Bu, Yuxiang; Gu, Lin; Sun, Xiaoming; Zhao, Huijun; Wang, Dingsheng; Li, Yadong. Dual-atom Pt heterogeneous catalyst with excellent catalytic performances for the selective hydrogenation and epoxidation. Nature Communications. 2021, 12 (1). ISSN 2041-1723. doi:10.1038/s41467-021-23517-x （英语）.
^ 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）.
^ Krishnan, Saravanan; Patel, Paresh N.; Balasubramanian, Kalpattu K.; Chadha, Anju. Yeast supported gold nanoparticles: an efficient catalyst for the synthesis of commercially important aryl amines. New Journal of Chemistry. 2021, 45 (4): 1915–1923. ISSN 1144-0546. doi:10.1039/D0NJ04542J （英语）.
^ Monsen, Paige J.; Luzzio, Frederick A. Applicability of aluminum amalgam to the reduction of arylnitro groups. Tetrahedron Letters. 2020, 61 (47): 152575. ISSN 0040-4039. doi:10.1016/j.tetlet.2020.152575 （英语）.
^ 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）.
^ 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）.
^ 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）.
^ 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）.
^ 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）.
^ Zhao, Wenqi; Zhang, Feng; Deng, Guo-Jun. Iodine/DMSO-Promoted Selective Direct Arylthiation of Anilines with Thiols under Metal-Free Conditions. The Journal of Organic Chemistry. 2020, 86 (1): 291–301. ISSN 0022-3263. doi:10.1021/acs.joc.0c02078 （英语）.

[NLM-1] 1.0 ^1.1 ^1.2 "Hazardous Substances Data Bank" data were obtained from the National Library of Medicine (US). SciFinder. [2021-07-12]. （原始内容存档于2020-04-19）（英语）.

[2] Tian, Shubo; Wang, Bingxue; Gong, Wanbing; He, Zizhan; Xu, Qi; Chen, Wenxing; Zhang, Qinghua; Zhu, Youqi; Yang, Jiarui; Fu, Qiang; Chen, Chun; Bu, Yuxiang; Gu, Lin; Sun, Xiaoming; Zhao, Huijun; Wang, Dingsheng; Li, Yadong. Dual-atom Pt heterogeneous catalyst with excellent catalytic performances for the selective hydrogenation and epoxidation. Nature Communications. 2021, 12 (1). ISSN 2041-1723. doi:10.1038/s41467-021-23517-x （英语）.

[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）.

[4] Krishnan, Saravanan; Patel, Paresh N.; Balasubramanian, Kalpattu K.; Chadha, Anju. Yeast supported gold nanoparticles: an efficient catalyst for the synthesis of commercially important aryl amines. New Journal of Chemistry. 2021, 45 (4): 1915–1923. ISSN 1144-0546. doi:10.1039/D0NJ04542J （英语）.

[5] Monsen, Paige J.; Luzzio, Frederick A. Applicability of aluminum amalgam to the reduction of arylnitro groups. Tetrahedron Letters. 2020, 61 (47): 152575. ISSN 0040-4039. doi:10.1016/j.tetlet.2020.152575 （英语）.

[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）.

[11] Zhao, Wenqi; Zhang, Feng; Deng, Guo-Jun. Iodine/DMSO-Promoted Selective Direct Arylthiation of Anilines with Thiols under Metal-Free Conditions. The Journal of Organic Chemistry. 2020, 86 (1): 291–301. ISSN 0022-3263. doi:10.1021/acs.joc.0c02078 （英语）.

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