有机合成中间体。黄色针状结晶,熔点226℃,能升华,氧化后生成蒽醌。溶于热苯和热甲苯,微溶于醇、醚和冷苯,不溶于水。
有机合成中间体
合成路线 1(1. 合成:523-27-3)
- 步骤:在室温下,将Br₂(2.90mL,56.60mmol)的CHCl₃(50mL)溶液滴加到蒽(5.0g,28.05mmol)的CHCl₃(100mL)溶液中。搅拌4小时后,除去溶剂,粗产物用二氯甲烷重结晶纯化,得到黄色针状物。
- 条件:With bromine In chloroform at 20℃; for 4 h。
- 产率:98%。
- 表征:¹H NMR(500MHz,TMS,CDCl₃):δ(ppm)= 8.59-8.56(m,4H),7.64-7.61(m,4H);IR(KBr,cm⁻¹):2920,2850,1650,1560,1460,1380,1260,926,746,579;元素分析:C 14 H 8 Br₂计算值:C,54.04;H,2.40。实测值:C,53.84;H,2.36;MS,m/z:cal:336.0,实测值:336.1。
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合成路线 2(2. 合成:523-27-3)
- 步骤:将固体蒽(100g,0.56mol)加入装有1.5L二氯甲烷的3L圆底烧瓶中,搅拌30分钟直至蒽几乎完全溶解。然后在6小时内逐滴加入溴(58.5ml,185g,1.17mol)。反应混合物再搅拌24小时(直至观察不到HBr释放)。使用烧结玻璃过滤器过滤黄色沉淀物,滤液用冷二氯甲烷洗涤数次。母液再次搅拌7小时,再次形成沉淀,收集沉淀物。将获得的黄色粉末在高真空下干燥7小时。
- 条件:for 24 h;不需要Schlenk条件;反应瓶不能关闭,通风柜需要良好的通风。
- 产率:75%。
- 表征:元素分析:实测值:C = 51.72%,H = 1.85%;计算:C = 50.29%,H = 2.39%。
- 参考文献:[1] Inorganica Chimica Acta, 2013, vol. 396, p. 1-5。
其他合成方法
由蒽溴化而得。溴化反应在室温进行,以四氯化碳作溶剂。采用80-85%蒽为原料,加溴反应半小时,产率83-88%。