4,7-二溴-2,1,3-苯并噻二唑是用于构建OLED的有用构建基块；是一种有机中间体，可用于化学合成和材料科学领域，如制备发光和导电聚合物；可通过苯并噻二唑溴代反应制备，也可由苯-1,2-二胺先关环制备苯并[c][1,2,5]噻二唑后再溴代得到。
化学合成；材料科学
路线1：
- 步骤: 将10g（73.4mmol）中间体和100ml 48％氢溴酸混合，在室温下滴加35g（22.3mmol）溴，并将反应加热回流6小时，冷却至室温，加入100ml饱和亚硫酸氢钠水溶液，滤器，滤饼再用水洗涤，乙醇重结晶，得20.7g黄色固体。
- 条件: 加热回流6小时；室温滴加溴
- 收率: 96%
- 参考文献: [1] Polymer, 2010, vol. 51, # 26, p. 6123 - 6131；[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 18, p. 4982 - 4986；[3] Angew. Chem., 2017, vol. 129, # 18, p. 5064 - 5068,5；[4] Patent: CN106967060, 2017, A. Location in patent: Paragraph 0059; 0062-0063；[5] Tetrahedron, 2005, vol. 61, # 46, p. 10975 - 10982；[6] Tetrahedron Letters, 2005, vol. 46, # 40, p. 6843 - 6846；[7] European Journal of Organic Chemistry, 2006, # 21, p. 4924 - 4933；[8] Chemical Communications, 2011, vol. 47, # 33, p. 9471 - 9473；[9] Macromolecules, 2012, vol. 45, # 5, p. 2367 - 2376；[10] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2015, vol. 149, p. 157 - 165；[11] RSC Advances, 2016, vol. 6, # 26, p. 21387 - 21395；[12] Journal of Polymer Science, Part A: Polymer Chemistry, 2017, vol. 55, # 22, p. 3705 - 3715；[13] New Journal of Chemistry, 2017, vol. 41, # 23, p. 14635 - 14645；[14] New Journal of Chemistry, 2013, vol. 37, # 10, p. 3084 - 3091；[15] Polymer, 2015, vol. 79, p. 12 - 20；[16] Chemistry - A European Journal, 2017, vol. 23, # 26, p. 6441 - 6451；[17] New Journal of Chemistry, 2018, vol. 42, # 16, p. 13565 - 13572；[18] Macromolecules, 2005, vol. 38, # 2, p. 244 - 253；[19] Polymer, 2010, vol. 51, # 1, p. 62 - 68；[20] Journal of Polymer Science, Part A: Polymer Chemistry, 2010, vol. 48, # 7, p. 1607 - 1616；[21] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2014, vol. 128, p. 197 - 206；[22] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 2, p. 369 - 380；[23] Patent: JP2016/509621, 2016, A. Location in patent: Paragraph 0130-0131；[24] Dalton Transactions, 2017, vol. 46, # 18, p. 5918 - 5929；[25] Asian Journal of Chemistry, 2015, vol. 27, # 7, p. 2427 - 2430；[26] Dyes and Pigments, 2018, vol. 149, p. 399 - 406；[27] Patent: EP2333017, 2011, A1. Location in patent: Page/Page column 8；[28] New Journal of Chemistry, 2012, vol. 36, # 3, p. 550 - 553；[29] Journal of Materials Chemistry C, 2015, vol. 3, # 35, p. 9145 - 9153；[30] Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12533 - 12537；[31] Angew. Chem., 2016, vol. 128, # 40, p. 12721 - 12725,5；[32] Helvetica Chimica Acta, 2002, vol. 85, # 7, p. 2195 - 2213；[33] Macromolecules, 2013, vol. 46, # 6, p. 2078 - 2091；[34] Dyes and Pigments, 2016, vol. 124, p. 268 - 276；[35] Chemistry - An Asian Journal, 2016, vol. 11, # 14, p. 2016 - 2020；[36] Polymer, 2016, vol. 101, p. 208 - 216；[37] Organic Letters, 2009, vol. 11, # 19, p. 4450 - 4453；[38] Chemical Communications, 2015, vol. 51, # 25, p. 5298 - 5301；[39] Tetrahedron, 2015, vol. 71, # 23, p. 3838 - 3843；[40] Tetrahedron, 2016, vol. 72, # 23, p. 3232 - 3239；[41] Patent: US2012/305901, 2012, A1. Location in patent: Page/Page column 5-6；[42] Helvetica Chimica Acta, 2014, vol. 97, # 11, p. 1453 - 1468；[43] Chinese Journal of Chemistry, 2015, vol. 33, # 8, p. 873 - 880；[44] Macromolecules, 2016, vol. 49, # 7, p. 2549 - 2558；[45] Patent: CN108129495, 2018, A. Location in patent: Paragraph 0043; 0045; 0047；[46] Dyes and Pigments, 2016, vol. 126, p. 209 - 217；[47] Dyes and Pigments, 2016, vol. 135, p. 26 - 35；[48] Journal of the Brazilian Chemical Society, 2018, vol. 29, # 7, p. 1388 - 1399；[49] Journal of the American Chemical Society, 2012, vol. 134, # 5, p. 2599 - 2612；[50] Chemical Communications, 2015, vol. 51, # 54, p. 10864 - 10867；[51] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 863 - 873；[52] Patent: KR101495152, 2015, B1. Location in patent: Paragraph 0098-0101；[53] Journal of Polymer Science, Part A: Polymer Chemistry, 2010, vol. 48, # 20, p. 4456 - 4464；[54] Materials Research Bulletin, 2015, vol. 70, p. 865 - 875；[55] Chemical Communications, 2017, vol. 53, # 95, p. 12790 - 12793；[56] Journal of Materials Chemistry C, 2015, vol. 3, # 7, p. 1595 - 1603；[57] Patent: CN103992315, 2016, B. Location in patent: Paragraph 0033-0036；[58] RSC Advances, 2016, vol. 6, # 65, p. 60308 - 60317；[59] Organic Letters, 2009, vol. 11, # 4, p. 903 - 906；[60] Patent: US2011/152246, 2011, A1. Location in patent: Page/Page column 177；[61] Journal of Materials Chemistry A, 2014, vol. 2, # 8, p. 2657 - 2662；[62] Angewandte Chemie - International Edition, 2009, vol. 48, # 9, p. 1664 - 1668；[63] Chemical Communications, 2010, vol. 46, # 27, p. 4896 - 4898；[64] Polymer, 2013, vol. 54, # 14, p. 3542 - 3547；[65] Patent: KR101598183, 2016, B1. Location in patent: Paragraph 0197-0201；[66] Synthetic Communications, 2016, vol. 46, # 12, p. 1052 - 1061；[67] Journal of Physical Chemistry B, 2012, vol. 116, # 24, p. 7259 - 7268；[68] Chinese Journal of Chemistry, 2014, vol. 32, # 4, p. 298 - 306；[69] Journal of the American Chemical Society, 2004, vol. 126, # 7, p. 1942 - 1943；[70] Macromolecules, 2011, vol. 44, # 12, p. 4767 - 4776；[71] RSC Advances, 2014, vol. 4, # 46, p. 24377 - 24383；[72] Journal of Polymer Science, Part A: Polymer Chemistry, 2018, vol. 56, # 4, p. 376 - 386；[73] Journal of Materials Chemistry, 2011, vol. 21, # 21, p. 7714 - 7722；[74] New Journal of Chemistry, 2015, vol. 39, # 4, p. 2795 - 2806；[75] Chemical Communications, 2018, vol. 54, # 59, p. 8178 - 8181；[76] RSC Advances, 2016, vol. 6, # 53, p. 47676 - 47686；[77] Patent: EP1749823, 2007, A1. Location in patent: Page/Page column 30；[78] Journal of Heterocyclic Chemistry, 1970, vol. 7, p. 629 - 633；[79] Journal of the American Chemical Society, 2005, vol. 127, # 14, p. 5186 - 5195；[80] Macromolecules, 2005, vol. 38, # 18, p. 7636 - 7644；[81] Journal of Materials Chemistry, 2007, vol. 17, # 14, p. 1353 - 1355；[82] Chemical Communications, 2008, # 42, p. 5315 - 5317；[83] Journal of Materials Chemistry, 2009, vol. 19, # 41, p. 7730 - 7737；[84] Synlett, 2010, # 12, p. 1841 - 1844；[85] Organic Electronics: physics, materials, applications, 2010, vol. 11, # 2, p. 311 - 321；[86] Patent: EP2266982, 2010, A1. Location in patent: Page/Page column 23-24；[87] Chemical Communications, 2011, vol. 47, # 13, p. 3933 - 3935；[88] Patent: WO2011/52805, 2011, A1. Location in patent: Page/Page column 72-74；[89] Electrochimica Acta, 2011, vol. 56, # 5, p. 2263 - 2268；[90] New Journal of Chemistry, 2011, vol. 35, # 6, p. 1327 - 1334；[91] Chemistry of Materials, 2010, vol. 22, # 24, p. 6736 - 6741；[92] Journal of Materials Chemistry, 2011, vol. 21, # 12, p. 4679 - 4688；[93] Journal of Materials Chemistry, 2011, vol. 21, # 32, p. 11822 - 11830；[94] Organic Electronics: physics, materials, applications, 2010, vol. 11, # 12, p. 1877 - 1885；[95] Inorganic Chemistry Communications, 2011, vol. 14, # 11, p. 1719 - 1722；[96] Chemistry of Materials, 2010, vol. 22, # 13, p. 4034 - 4044；[97] Patent: US8110673, 2012, B2；[98] Macromolecules, 2010, vol. 43, # 6, p. 2873 - 2879；[99] Polymer, 2010, vol. 51, # 14, p. 3196 - 3202；[100] Molecular Crystals and Liquid Crystals, 2011, vol. 539, p. 428 - 435；[101] Polymer, 2010, vol. 51, # 15, p. 3425 - 3430；[102] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 2, p. 417 - 423；[103] Reactive and Functional Polymers, 2011, vol. 71, # 2, p. 168 - 174；[104] Macromolecules, 2011, vol. 44, # 15, p. 5994 - 6001；[105] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 17, p. 3499 - 3506；[106] Macromolecules, 2011, vol. 44, # 13, p. 5200 - 5208；[107] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 15, p. 3355 - 3365；[108] Journal of Nanoscience and Nanotechnology, 2012, vol. 12, # 5, p. 4365 - 4369；[109] Macromolecules, 2012, vol. 45, # 4, p. 1847 - 1857；[110] Dyes and Pigments, 2012, vol. 95, # 2, p. 229 - 235；[111] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 8, p. 1622 - 1635；[112] Electrochimica Acta, 2012, vol. 67, p. 224 - 229；[113] Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 9, p. 1933 - 1941；[114] Journal of Organic Chemistry, 2013, vol. 78, # 10, p. 4940 - 4948
路线2：
- 步骤: 步骤1：中间体V的合成将苯并噻二唑（5.00G，36.7mmol），48％HBr（50mL）和溴（4.1mL，80mmol）的混合物搅拌并在120℃下在回流冷凝器下加热16小时。将热的反应混合物在4L烧杯中缓慢倒入碎冰（1kG）和碳酸氢钠（0.2kG）的混合物中，搅拌1小时并用20％THF的DCM溶液（2×500mL）萃取。萃取液用硫酸镁干燥，减压除去溶剂。将残余物用热乙醇（100mL）研磨并在室温下放置2小时。滤出晶体并干燥，得到4,7-二溴苯并噻二唑。
- 条件: 120℃加热16小时；热反应混合物倒入碎冰和碳酸氢钠混合物中；用20％THF的DCM溶液萃取；热乙醇研磨
- 收率: 89%
- 参考文献: [1] Patent: US2013/74927, 2013, A1. Location in patent: Paragraph 0274; 0275
