4-氟-7-硝基苯并-2-氧杂-1,3-二唑性质、用途与生产工艺
NBD-F (4-Fluoro-7-nitrobenzofurazan) 是一种用于氨基酸分析 (amino acid analysis) 的前荧光试剂。NBD-F 与一级或二级胺反应生成荧光产物，用于分析氨基酸和低分子量胺。
As the percentage of the organic phase changes, the retention time of NBD-F remains relatively stable, while the retention times of the derivatization products changes. The pH of the mobile phase affects the separation of the NBD-F and the derivatization products. NBD-F is a fluorescent derivatization reagent that is originally developed for amino acid analysis, and recently applied to the analysis of other amino acid derivatives such as N-methyl-D-aspartic acid and glutathione. The use of NBD-F appears to have several advantages in that the derivatization procedure is simple and its derivatives are highly stable.
生产方法
以4-氟-2,1,3-苯并恶二唑为原料合成4-氟-7-硝基-2,1,3-苯并恶二唑的一般步骤：将4-氟-2,1,3-苯并恶二唑（1.00g，7.24mmol）溶于浓H2SO4（8mL）中，冷却至-10℃。在搅拌下，缓慢滴加硝化混合物（H2SO4:HNO3，3:1，2.40mL）。保持反应温度在-10℃，继续搅拌1小时。通过TLC和LCMS监测反应进度。反应完成后，将反应混合物用H2O（250mL）淬灭，并用EtOAc（2×250mL）萃取。合并有机层，用无水Na2SO4干燥，减压浓缩。粗产物通过快速柱色谱法（洗脱剂：己烷中0至10% EtOAc梯度）纯化，得到4-氟-7-硝基-2,1,3-苯并恶二唑（0.39g，黄色固体），产率30%。1H NMR（400MHz，DMSO-d6）δ 7.70（d，J=8.40Hz，1H），8.77-8.80（m，1H）。
参考文献：
[1] Journal of the American Chemical Society, 2016, vol. 138, # 48, p. 15596 - 15604
[2] Patent: WO2018/122232, 2018, A1. Location in patent: Page/Page column 213
[3] Tetrahedron Letters, 2011, vol. 52, # 20, p. 2533 - 2535
4-氟-7-硝基苯并-2-氧杂-1,3-二唑
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