Synthesis Of Haptens For Tris (2,3-dibromopropyl) Isocyanurate Containing Carboxyl Function Group

Most of persistent organic pollutants (POPs) have carcinogenic, teratogenic, mutagenic nature, they can persist in the environment and they are difficult to break down; they have a strong biological enrichment effect, resulting in the poisoning through the food chain transfer and biomagnification;they can long-distance transform and possess highly toxic. these features resulting in persistent organic pollutants causing serious harm to human health and the ecological environment, at present POPs have given rise to the widespread concern of the international community organizations.Tris (2,3-dibromopropyl) isocyanurate (TBC) is a brominated flame retardant, it was extensive used in the synthesis plastics, rubber and other chemical industrial products. Recently, through detection the polluted water by TBC and QSPR model calculation, both confirmed TBC has all the major characteristics of POPs, which is defined as the potential of POPs. at present the methods of detection TBC mainly rely on the instrumental analysis(GC-MS, HPLC and so on), the method is expensive, time-consuming, and many other limiting factors are not popular, immunoassay technique with high sensitivity, high specificity, quick and easy advantage aroused the people’s attention, so the establishment of TBC immunoassay detection technology has an important significance.The immunoassay is based on the specificity of the antigen-antibody binding to the basic principle, the key of the immunoassay technology is to prepare a high-quality antigen, TBC is a small molecules, which has no immunogenic, it must be coupled to the carrier protein to prepare the adult workers antigen, which induce the body to produce specific antibodies, to create TBC immunoassay detection, design and synthesis of the hapten molecules, which are effective coupling the carried protein and contain the TBC precursor structure, are very important. Based on this, we have done the following work:Firstly, Through TBC molecular structure analysis, we determined the total synthesis method Synthesis TBC hapten molecule. By Claisen rearrangement reaction to give an important intermediate compound 3, because compound 3 is essential for the entire experiment, through many experiments exploring, we optimize the reaction conditions, the reaction yield from 15% to 72%, ensuring our experiments smoothly implement.Secondly, Compound 4 having a strong nucleophilic and having a best Coupling bit point, different types of structure and the length of the connecting arms can be introduced. In order to explore the impact of the length of the connecting arm to produce antibodies. Through the nucleophilic, brominated addition, the hydrolysis of the esters, we successfully synthesized three fat carboxylic acid TBC hapten molecules, which have the different connecting arm length and contain part of the reservation of the TBC parent structure.Thirdly, In order to maximize on retain the characteristic structure of the TBC, Through Steglich esterification, Williamson ether-forming reaction, bromide addition, potassium permanganate oxidation, trifluoroacetic acid hydrolysis reaction and so on, we successfully synthesized three aromatic carboxylic acids TBC hapten molecules, which have different connecting arm length and completely retained TBC parent structure, We can further explore the impact of the benzene ring structure to produce antibody specificity.