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维基百科

3-溴甲苯

四月 01, 2023

3-溴甲苯是一种有机化合物，化学式为C7H7Br，是溴甲苯的同分异构体之一。

3-溴甲苯
别名 间溴甲苯
3-甲基溴苯
识别
CAS号 591-17-3  
PubChem 11560
SMILES
性质
化学式 C7H7Br
摩尔质量 171.03 g·mol−1
外观 无色液体
密度 1.4022 g·cm−3（25 °C）[1]
熔点 −39.8 °C（233.3 K）[2]
沸点 183.7 °C（456.8 K）[2]
溶解性（水） 难溶
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

合成

3-溴甲苯可由3-溴苯甲醛在钯碳催化剂存在下被氢气还原得到，[3]或通过3-甲基苯胺的重氮化-溴化反应制得。[4]3-甲基苯肼盐酸盐和三溴化硼在二甲基亚砜中反应，也可以得到3-溴甲苯。[5]

反应

3-溴甲苯和苯硼酸可以发生铃木偶联反应（C–C偶联），生成3-甲基联苯：[6]

 

类似地，在三(二亚苄基丙酮)二钯催化下，它和格式试剂可以发生熊田偶联反应，如和4-甲氧基苯基溴化镁反应，得到3-甲基-4'-甲氧基联苯。[7]该催化剂也可催化3-溴甲苯与胺的反应，如3-溴甲苯和哌啶在碱的存在下反应，可以得到C–C偶联产物1-(3-甲基苯基)哌啶。[8]

乙酸钯和三苯基膦可以催化其脱溴反应：[9]

 

它和氯磺酸在三氯甲烷中反应，可以得到4-溴-2-甲苯磺酰氯。[10]它可以被氧气、过氧化叔丁醇等氧化剂催化氧化为3-溴苯甲酸。[11][12][13]

参考文献

  1. ^ Hussey, Allen S.; Dyer, John R. The Monomagnesium Derivatives of Dibromotoluenes. Journal of the American Chemical Society. 2002, 73 (2): 603–604. ISSN 0002-7863. doi:10.1021/ja01146a031. 
  2. ^ 2.0 2.1 "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2021-07-11].
  3. ^ Wang, Shuguo; Zhou, Peng; Jiang, Liang; Zhang, Zehui; Deng, Kejian; Zhang, Yuhua; Zhao, Yanxi; Li, Jinlin; Bottle, Steven; Zhu, Huaiyong. Selective deoxygenation of carbonyl groups at room temperature and atmospheric hydrogen pressure over nitrogen-doped carbon supported Pd catalyst. Journal of Catalysis. 2018, 368: 207–216. ISSN 0021-9517. doi:10.1016/j.jcat.2018.10.017. 
  4. ^ Beletskaya, Irina; Sigeev, Alexander; Peregudov, Alexander; Petrovskii, Pavel. Catalytic Sandmeyer Bromination. Synthesis. 2007, 2007 (16): 2534–2538. ISSN 0039-7881. doi:10.1055/s-2007-983784. 
  5. ^ Phuc Tran, Dat; Nomoto, Akihiro; Mita, Soichiro; Dong, Chun-ping; Kodama, Shintaro; Mizuno, Takumi; Ogawa, Akiya. Metal- and base-free synthesis of aryl bromides from arylhydrazines. Tetrahedron Letters. 2020, 61 (23): 151959. ISSN 0040-4039. doi:10.1016/j.tetlet.2020.151959. 
  6. ^ Wang, Ai-E; Zhong, Jun; Xie, Jian-Hua; Li, Kai; Zhou, Qi-Lin. Highly Efficient Suzuki Cross-Coupling Catalyzed by Palladium/Phosphine-Imidazolium Carbene System. Advanced Synthesis & Catalysis. 2004, 346 (6): 595–598. ISSN 1615-4150. doi:10.1002/adsc.200404015. 
  7. ^ Pal, Anwesha; Ghosh, Raju; Adarsh, N.N.; Sarkar, Amitabha. Pyrazole-tethered phosphine ligands for Pd(0): useful catalysts for Stille, Kumada and Hiyama cross-coupling reactions. Tetrahedron. 2010, 66 (29): 5451–5458. ISSN 0040-4020. doi:10.1016/j.tet.2010.05.026. 
  8. ^ Mudithanapelli, Chandrashekar; Dhorma, Lama Prema; Kim, Mi-hyun. PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp2)–H or C(sp3)–H: Nitration via C–N Bond Cleavage of CH3NO2, Cyanation, or Oxygenation in Water. Organic Letters. 2019, 21 (9): 3098–3102. ISSN 1523-7060. doi:10.1021/acs.orglett.9b00751. 
  9. ^ Chen, Jingbo; Zhang, Yushun; Yang, Liquan; Zhang, Xiang; Liu, Jianping; Li, Liang; Zhang, Hongbin. A practical palladium catalyzed dehalogenation of aryl halides and α-haloketones. Tetrahedron. 2007, 63 (20): 4266–4270. ISSN 0040-4020. doi:10.1016/j.tet.2007.03.061. 
  10. ^ Chen, Qiao-Hong; Rao, P.N. Praveen; Knaus, Edward E. Design, synthesis, and biological evaluation of N-acetyl-2-carboxybenzenesulfonamides: a novel class of cyclooxygenase-2 (COX-2) inhibitors. Bioorganic & Medicinal Chemistry. 2005, 13 (7): 2459–2468. ISSN 0968-0896. doi:10.1016/j.bmc.2005.01.039. 
  11. ^ Zheng, Kun; Yan, Xiaoyu; Zhang, Guofu; Yan, Xinhuan; Li, Xiaoqing; Xu, Xiangsheng. Photoinduced Carbon Tetrabromide Initiated Aerobic Oxidation of Substituted Toluenes to Carboxylic Acids. Synlett. 2019, 31 (03): 272–274. ISSN 0936-5214. doi:10.1055/s-0039-1691534. 
  12. ^ Ozen, Recep. Pyridinium Chlorochromate Catalyzed Oxidation of Toluenes to Aromatic Carboxylic Acids with Molecular Oxygen in Sub-critical Water. Asian Journal of Chemistry. 2014, 26 (3): 941–942. ISSN 0970-7077. doi:10.14233/ajchem.2014.16651. 
  13. ^ Mohammadpour, Pegah; Safaei, Elham. Catalytic C–H aerobic and oxidant-induced oxidation of alkylbenzenes (including toluene derivatives) over VO2+ immobilized on core–shell Fe3O4@SiO2 at room temperature in water. RSC Advances. 2020, 10 (40): 23543–23553. ISSN 2046-2069. doi:10.1039/D0RA03483E. 

四月 01, 2023
溴甲苯, 是一种有机化合物, 化学式为c7h7br, 是溴甲苯的同分异构体之一, 别名, 间溴甲苯3, 甲基溴苯识别cas号, pubchem, 11560smiles, br性质化学式, c7h7br摩尔质量, 1外观, 无色液体密度, 4022, 熔点, 沸点, 溶解性, 难溶若非注明, 所有数据均出自标准状态, 合成, 编辑可由3, 溴苯甲醛在钯碳催化剂存在下被氢气还原得到, 或通过3, 甲基苯胺的重氮化, 溴化反应制得, 甲基苯肼盐酸盐和三溴化硼在二甲基亚砜中反应, 也可以得到, 反应, 编辑和苯硼酸可以发. 3 溴甲苯是一种有机化合物 化学式为C7H7Br 是溴甲苯的同分异构体之一 3 溴甲苯别名 间溴甲苯3 甲基溴苯识别CAS号 591 17 3 PubChem 11560SMILES CC1 CC CC C1 Br性质化学式 C7H7Br摩尔质量 171 03 g mol 1外观 无色液体密度 1 4022 g cm 3 25 C 1 熔点 39 8 C 233 3 K 2 沸点 183 7 C 456 8 K 2 溶解性 水 难溶若非注明 所有数据均出自标准状态 25 100 kPa 下 合成 编辑3 溴甲苯可由3 溴苯甲醛在钯碳催化剂存在下被氢气还原得到 3 或通过3 甲基苯胺的重氮化 溴化反应制得 4 3 甲基苯肼盐酸盐和三溴化硼在二甲基亚砜中反应 也可以得到3 溴甲苯 5 反应 编辑3 溴甲苯和苯硼酸可以发生铃木偶联反应 C C偶联 生成3 甲基联苯 6 类似地 在三 二亚苄基丙酮 二钯催化下 它和格式试剂可以发生熊田偶联反应 如和4 甲氧基苯基溴化镁反应 得到3 甲基 4 甲氧基联苯 7 该催化剂也可催化3 溴甲苯与胺的反应 如3 溴甲苯和哌啶在碱的存在下反应 可以得到C C偶联产物1 3 甲基苯基 哌啶 8 乙酸钯和三苯基膦可以催化其脱溴反应 9 它和氯磺酸在三氯甲烷中反应 可以得到4 溴 2 甲苯磺酰氯 10 它可以被氧气 过氧化叔丁醇等氧化剂催化氧化为3 溴苯甲酸 11 12 13 参考文献 编辑 Hussey Allen S Dyer John R The Monomagnesium Derivatives of Dibromotoluenes Journal of the American Chemical Society 2002 73 2 603 604 ISSN 0002 7863 doi 10 1021 ja01146a031 2 0 2 1 PhysProp data were obtained from Syracuse Research Corporation of Syracuse New York US Retrieved from SciFinder 2021 07 11 Wang Shuguo Zhou Peng Jiang Liang Zhang Zehui Deng Kejian Zhang Yuhua Zhao Yanxi Li Jinlin Bottle Steven Zhu Huaiyong Selective deoxygenation of carbonyl groups at room temperature and atmospheric hydrogen pressure over nitrogen doped carbon supported Pd catalyst Journal of Catalysis 2018 368 207 216 ISSN 0021 9517 doi 10 1016 j jcat 2018 10 017 Beletskaya Irina Sigeev Alexander Peregudov Alexander Petrovskii Pavel Catalytic Sandmeyer Bromination Synthesis 2007 2007 16 2534 2538 ISSN 0039 7881 doi 10 1055 s 2007 983784 Phuc Tran Dat Nomoto Akihiro Mita Soichiro Dong Chun ping Kodama Shintaro Mizuno Takumi Ogawa Akiya Metal and base free synthesis of aryl bromides from arylhydrazines Tetrahedron Letters 2020 61 23 151959 ISSN 0040 4039 doi 10 1016 j tetlet 2020 151959 Wang Ai E Zhong Jun Xie Jian Hua Li Kai Zhou Qi Lin Highly Efficient Suzuki Cross Coupling Catalyzed by Palladium Phosphine Imidazolium Carbene System Advanced Synthesis amp Catalysis 2004 346 6 595 598 ISSN 1615 4150 doi 10 1002 adsc 200404015 Pal Anwesha Ghosh Raju Adarsh N N Sarkar Amitabha Pyrazole tethered phosphine ligands for Pd 0 useful catalysts for Stille Kumada and Hiyama cross coupling reactions Tetrahedron 2010 66 29 5451 5458 ISSN 0040 4020 doi 10 1016 j tet 2010 05 026 Mudithanapelli Chandrashekar Dhorma Lama Prema Kim Mi hyun PIFA Promoted Solvent Controlled Selective Functionalization of C sp2 H or C sp3 H Nitration via C N Bond Cleavage of CH3NO2 Cyanation or Oxygenation in Water Organic Letters 2019 21 9 3098 3102 ISSN 1523 7060 doi 10 1021 acs orglett 9b00751 Chen Jingbo Zhang Yushun Yang Liquan Zhang Xiang Liu Jianping Li Liang Zhang Hongbin A practical palladium catalyzed dehalogenation of aryl halides and a haloketones Tetrahedron 2007 63 20 4266 4270 ISSN 0040 4020 doi 10 1016 j tet 2007 03 061 Chen Qiao Hong Rao P N Praveen Knaus Edward E Design synthesis and biological evaluation of N acetyl 2 carboxybenzenesulfonamides a novel class of cyclooxygenase 2 COX 2 inhibitors Bioorganic amp Medicinal Chemistry 2005 13 7 2459 2468 ISSN 0968 0896 doi 10 1016 j bmc 2005 01 039 Zheng Kun Yan Xiaoyu Zhang Guofu Yan Xinhuan Li Xiaoqing Xu Xiangsheng Photoinduced Carbon Tetrabromide Initiated Aerobic Oxidation of Substituted Toluenes to Carboxylic Acids Synlett 2019 31 03 272 274 ISSN 0936 5214 doi 10 1055 s 0039 1691534 Ozen Recep Pyridinium Chlorochromate Catalyzed Oxidation of Toluenes to Aromatic Carboxylic Acids with Molecular Oxygen in Sub critical Water Asian Journal of Chemistry 2014 26 3 941 942 ISSN 0970 7077 doi 10 14233 ajchem 2014 16651 Mohammadpour Pegah Safaei Elham Catalytic C H aerobic and oxidant induced oxidation of alkylbenzenes including toluene derivatives over VO2 immobilized on core shell Fe3O4 SiO2 at room temperature in water RSC Advances 2020 10 40 23543 23553 ISSN 2046 2069 doi 10 1039 D0RA03483E 取自 https zh wikipedia org w index php title 3 溴甲苯 amp oldid 66533995, 维基百科，wiki，书籍，书籍，图书馆，

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