Br-,I-精确取代萘环1,4活化位合成及结构表征  

Synthesis and Structural Characterization of Br-, I-Precisely Substituted Naphthalene Ring 1,4 Activation Site

作　　者：杨杰[1] 吴绵园 吕宏飞[1] 李晓鹏[1] 梅立鑫 刘洋[1] YANG Jie;WU Mian-yuan;LV Hong-fei;LI Xiao-peng;MEI Li-xin;LIU Yang(Institute of Petrochemistry,Heilongjiang Academy of Sciences,Harbin 150040,China)

机构地区：[1]黑龙江省科学院石油化学研究院

出　　处：《化学与粘合》2020年第1期43-45,共3页Chemistry and Adhesion

基　　金：黑龙江省院所基本应用技术研究专项

摘　　要：以1-氨基萘为起始原料,乙酸酐提供保护基,在酸性条件下对氨基进行保护,形成邻对位定位基,可有效在萘环4位上精确引入溴原子,再在碱性条件下去除氨基保护基,通过重氮化法精确取代萘环上的1位来合成1-溴-4-碘萘及1,4-二溴萘。通过红外光谱、热重及紫外吸收光谱,对其结构、热稳定性及光谱吸收进行了分析。1-溴-4-碘萘的热分解温度为179℃,紫外吸收波长在230nm,285nm,296nm,306nm;1,4-二溴萘的热分解温度为187℃,紫外吸收波长在230nm,289nm,301nm,314nm。With 1-aminonaphthalene as raw material, the acetic anhydride as a protecting group, which protects the amino group under acidic conditions to form an ortho-positionable group, the bromine atom can be effectively set on the 4-position of the naphthalene ring;and then under ba-sic conditions, the amino protecting group is removed, and the 1-bromo-4-iodophthalene and 1,4-dibromonaphthalene are synthesized by precisely replacing the 1-position on the naphthalene ring by diazotization. The structure, thermal stability and spectral absorption are analyzed by infrared spectroscopy, thermogravimetry and ultraviolet absorption spectroscopy. The thermal decomposition temperature of 1-bromo-4-iodophthalene is 179 ℃,the ultraviolet absorption wavelength is at 230 nm, 285 nm, 296 nm, 306 nm;the thermal decomposition temperature of 1,4-dibromonaphthalene is 187 ℃,and the ultraviolet absorption wavelength is at 230 nm, 289 nm, 301 nm, 314 nm.

关 键 词：1-乙酰萘胺 重氮化 1-溴-4-碘萘 1 4-二溴萘 

分 类 号：TQ150.4[化学工程—电化学工业]