Chemical Properties
Off-White to Tan Solid
Uses
2-(3-Amino-phenyl)-benzooxazol-5-ylamine can be used to prepare high-strength flexible transparent polyimide materials.
Application
2-(3-Amino-phenyl)-benzooxazol-5-ylamine is primarily used as an intermediate in organic synthesis, particularly in polymer materials and medicinal chemistry. Specifically, it can be used as a monomer in high-temperature-resistant polymers such as polyimide (PI) to prepare high-performance polymers. Furthermore, its structural properties make it useful as a reagent in biochemical research, enabling the exploration of biological processes.
Synthesis
General procedure for the synthesis of 2-(4-aminophenyl)-5-aminobenzo[d]oxazole from 2-(4-nitrophenyl)-5-nitrobenzo[d]oxazole: 2-(4-nitrophenyl)-5-nitrobenzo[d]oxazole (3.22 g, 0.01 mol) was added to a 100 mL single-necked flask followed by the addition of 50 mL of water at room temperature. The pH of the reaction system was adjusted with phosphoric acid to 1. Then, sodium thiosulfate solid (8.5 g, 0.06 mol) was added and the reaction system was warmed up to 100 °C for 16 h. The reaction was completed by adding a solid sodium thiosulfate (8.5 g, 0.06 mol). After completion of the reaction, it was cooled to room temperature and filtered. To the filtrate, 25% by weight of aqueous sodium carbonate was added and neutralized to pH 7. At this point, the product 2-(4-aminophenyl)-5-aminobenzo[d]oxazole was precipitated from the reaction system, and after filtration, several washes, and drying, 2.14 g of the target product was obtained (95% yield, HPLC purity >99.9%).
References
[1] Patent: CN108558770, 2018, A. Location in patent: Paragraph 0082; 0083; 0084
[2] Chemical Biology and Drug Design, 2012, vol. 79, # 6, p. 1018 - 1024
[3] Patent: TWI558696, 2016, B. Location in patent: Paragraph 0035; 0040-0041
