- 急性毒性
口服-大鼠 LD:>500 毫克/公斤;静脉-小鼠 LD50: 100 毫克/公斤
- 可燃性危险特性
热分解排出有毒溴化物和氮氧化物烟雾
- 储运特性
库房通风低温干燥
- 灭火剂
水,干粉、干砂、二氧化碳、泡沫、1211灭火剂
医药; 农药
合成路线 1(1. 合成:13296-94-1)
产率:99%
合成条件:With pyrrolidone hydrotribromide In methanol; dichloromethane at 20℃; for 0.50 h;
实验步骤:在室温下,用PHT(6.30g,12.7mmol,1.1当量)处理4-硝基苯胺(1.60g,11.6mmol,1当量)在DCM(40mL)和MeOH(20mL)中的溶液。 方式。 然后继续搅拌0.5小时。 将混合物用Et 2 O(50mL)稀释,先用饱和Na 2 S 2 O 3水溶液(40mL)洗涤,然后用盐水(40mL)洗涤。 将有机萃取物用MgSO 4干燥,然后过滤并减压除去溶剂。 通过快速柱色谱法(c-Hex-EtOAc; 2:1)纯化,得到S8(2.50g,99%),为黄色固体。
参考文献:
- [1] Synthesis, 2004, # 17, p. 2809 - 2812 [2] Tetrahedron Letters, 2017, vol. 58, # 48, p. 4559 - 4562 [3] Tetrahedron Letters, 2005, vol. 46, # 51, p. 8959 - 8963 [4] Synthetic Communications, 2010, vol. 40, # 21, p. 3226 - 3232 [5] Journal of the American Chemical Society, 1994, vol. 116, # 26, p. 11797 - 11810 [6] Tetrahedron Letters, 2000, vol. 41, # 13, p. 2083 - 2085 [7] Synthetic Communications, 2004, vol. 34, # 12, p. 2143 - 2152 [8] Green Chemistry, 2011, vol. 13, # 8, p. 2187 - 2196 [9] Tetrahedron Letters, 2006, vol. 47, # 49, p. 8693 - 8697 [10] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 3, p. 496 - 501 [11] Russian Journal of Applied Chemistry, 2009, vol. 82, # 9, p. 1570 - 1576 [12] Angewandte Chemie - International Edition, 2006, vol. 45, # 43, p. 7255 - 7258 [13] Journal of the Iranian Chemical Society, 2016, vol. 13, # 11, p. 2019 - 2028 [14] Patent: CN107089919, 2017, A. Location in patent: Paragraph 0036; 0037; 0038; 0039 [15] Synthetic Communications, 2009, vol. 39, # 2, p. 215 - 219 [16] Synthetic Communications, 2009, vol. 39, # 23, p. 4212 - 4220 [17] Tetrahedron Letters, 2012, vol. 53, # 39, p. 5248 - 5252 [18] Tetrahedron Letters, 2010, vol. 51, # 10, p. 1383 - 1385 [19] Journal of the Chilean Chemical Society, 2011, vol. 56, # 4, p. 863 - 865 [20] Environmental Science and Technology, 2001, vol. 35, # 18, p. 3749 - 3756 [21] Heterocycles, 2004, vol. 63, # 11, p. 2457 - 2463 [22] Tetrahedron, 2003, vol. 59, # 6, p. 773 - 779 [23] Synthesis, 2005, # 7, p. 1103 - 1108 [24] Organic Letters, 2017, vol. 19, # 19, p. 5122 - 5125 [25] Letters in Organic Chemistry, 2018, vol. 15, # 8, p. 682 - 687 [26] Patent: CN106866425, 2017, A. Location in patent: Paragraph 0026-0029 [27] Angewandte Chemie - International Edition, 2017, vol. 56, # 38, p. 11554 - 11558 [28] Angew. Chem., 2017, vol. 129, # 38, p. 11712 - 11716,5 [29] Angewandte Chemie - International Edition, 2016, vol. 55, # 18, p. 5602 - 5605 [30] Angew. Chem., 2016, vol. 128, p. 5692 - 5696,5 [31] Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7360 - 7377 [32] Journal of the Chemical Society. Perkin Transactions 2, 2000, # 6, p. 1113 - 1118 [33] Patent: WO2008/100423, 2008, A1. Location in patent: Page/Page column 89-90 [34] Patent: WO2009/14674, 2009, A1. Location in patent: Page/Page column 82-83 [35] Applied Catalysis A: General, 2010, vol. 384, # 1-2, p. 18 - 26 [36] Patent: US2011/98311, 2011, A1 [37] Patent: US2015/231142, 2015, A1. Location in patent: Paragraph 1659; 1668 [38] Chemistry - A European Journal, 2017, vol. 23, # 5, p. 1044 - 1047 [39] Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 9.2, p. 1543 - 1544 [40] Zhurnal Organicheskoi Khimii, 1992, vol. 28, # 9, p. 1926 - 1927 [41] Tetrahedron, 2000, vol. 56, # 50, p. 9833 - 9841 [42] European Journal of Organic Chemistry, 2009, # 5, p. 687 - 698 [43] Journal of Medicinal Chemistry, 2009, vol. 52, # 12, p. 3703 - 3715 [44] Tetrahedron, 2009, vol. 65, # 22, p. 4429 - 4439 [45] RSC Advances, 2013, vol. 3, # 30, p. 12091 - 12095 [46] Patent: US2007/244159, 2007, A1. Location in patent: Page/Page column 117; 119; 128 [47] Patent: US2011/98311, 2011, A1 [48] ChemMedChem, 2017, vol. 12, # 16, p. 1390 - 1398 [49] Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 4, p. 621 - 630 [50] Synthetic Communications, 2009, vol. 39, # 10, p. 1817 - 1824 [51] Synthetic Communications, 2010, vol. 40, # 6, p. 868 - 876 [52] Synthetic Communications, 2007, vol. 37, # 6, p. 933 - 939 [53] Chemical Communications, 1996, # 23, p. 2679 - 2680 [54] Journal of the American Chemical Society, 1927, vol. 49, p. 1805 [55] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1914, vol. <5> 23 I, p. 283 [56] Journal of the Chemical Society, 1935, p. 1134,1137 [57] Journal of the Chemical Society, 1936, p. 311,315 [58] Synlett, 2005, # 2, p. 279 - 282 [59] Canadian Journal of Chemistry, 2005, vol. 83, # 3, p. 213 - 219 [60] South African Journal of Chemistry, 2006, vol. 59, p. 125 - 128 [61] Tetrahedron Letters, 2008, vol. 49, # 1, p. 189 - 194 [62] Tetrahedron Letters, 2012, vol. 53, # 2, p. 127 - 131 [63] Patent: US2011/98311, 2011, A1 [64] Journal of Materials Chemistry, 2012, vol. 22, # 22, p. 11268 - 11276 [65] Catalysis Letters, 2013, vol. 143, # 2, p. 225 - 233 [66] Synthesis (Germany), 2013, vol. 45, # 11, p. 1497 - 1504 [67] Chemistry - A European Journal, 2017, vol. 23, # 11, p. 2660 - 2665 [68] Patent: WO2017/156181, 2017, A1. Location in patent: Paragraph 00407 [69] Journal of Organometallic Chemistry, 2018, vol. 858, p. 37 - 46 [70] Patent: WO2009/3077, 2008, A1. Location in patent: Page/Page column 138
合成路线 2(3. 合成:13296-94-1)
产率:65.6%
合成条件:With bromine In water; acetic acid
实验步骤:实施例I 2-溴-4-硝基苯胺将100g(0.724mol)对硝基苯胺在40℃下缓慢加入1550ml冰醋酸中。将溶液冷却至20℃后,37.4ml(116.65g, 在1小时内逐滴加入0.730mol)溴,然后将溶液再搅拌45分钟。 通过抽滤收集反应过程中形成的沉淀,并与2500ml 10%亚硫酸氢钠水溶液一起搅拌16小时; 通过抽滤再次收集并用2500ml水洗涤。 将固体风干24小时。 将粗物质(139g)从65%甲醇中重结晶两次,得到103g(65.6%)黄色结晶固体,其在101℃-102℃下熔化。 IR(KBr)3500,3400,1125cm -1(NH 2); 1500,1325(NO2)。。计算。 C 6 H 5 N 2 O 2 Br:C,33.18; H,2.30; N,12.90。 实测值:C,33.26; H,2.28; N,12.92。
参考文献:
- [1] Patent: US754, 1990, H1