Description
It is usually used as the intermediate or raw material in the organic synthesis. For example, this chemical can be selected as the raw material to prepare three lanthanide metal organic frameworks (MOFs) with typical structural features of one-dimensional ladder-like chain, two-dimensional layer, and three-dimensional framework.
1 Moreover, this substance is chosen as the reactant to fabricate new metal complexes with 5-(1H-imidazol-4-ylmethyl)aminoisophthalic acid, which have good electrocatalytic activities toward the reduction of H2O2 in phosphate buffer (pH=5.5) solution.
2 In addition, as the active reactant, this chemical has been demonstrated to assist in the synthesis of a chiral, radically homopolymerizable methacrylamide dendrimer with eight ester groups.
3
Reference
- Jin, H. G.; Yan, Y. Z.; Li, J.; Gu, Z. G.; Chen, J. H.; Liu, Y. T.; Zheng, Z. P.; Zhan, Q. G.; Cai, Y. P., 1-D to 3-D lanthanide coordination polymers constructed from 5-aminoisophthalic acid and oxalic acid. Inorg. Chem. Commun. 2012, 23, 25-30.
- Xu, J.; Su, Z.; Chen, M. S.; Chen, S. S.; Sun, W. Y., New metal complexes with 5-(1H-imidazol-4-ylmethyl)aminoisophthalic acid: Syntheses, structures, electrochemistry and electrocatalysis. Inorg. Chim. Acta 2009, 362, 4002-4008.
- Draheim, G.; Ritter, H., POLYMERIZABLE DENDRIMERS SYNTHESIS OF A SYMMETRICALLY BRANCHED METHACRYL DERIVATIVE BEARING 8 ESTER GROUPS. Macromol. Chem. Phys. 1995, 196, 2211-2222.
Chemical Properties
Light beige-brown crystalline powder
Uses
5-Aminoisophthalic acid is a useful biochemical for proteomics research.
reaction suitability
reaction type: solution phase peptide synthesis
Synthesis
In a 3L four-neck flask equipped with a mechanical stirrer, 211.1 g (1.0 mol, 1.0 eq.) of 5-nitroisophthalic acid and 160.0 g (4.0 mol, 4.0 eq.) of sodium hydroxide were dissolved in 2L of water. A thermometer was installed and the mixture was stirred for 1 hour until the system was clarified. Subsequently, 10 g of Nguyenay nickel was added and the temperature was slowly raised to 30-35°C. At this temperature, 125.0 g (2.0 mol, 2.0 eq.) of 80% hydrazine hydrate was added dropwise for a controlled drop time of 30 minutes. After dropwise addition, stirring was continued for 30 min to ensure complete reaction. At the end of the reaction, the pH of the filtrate was adjusted to 3.5-4.0 with acetic acid and a large amount of white solid was precipitated. The precipitate was collected by filtration and dried to give 172.0 g of 5-aminoisophthalic acid in 95% yield and 99.7% purity.
References
[1] Nucleosides and Nucleotides, 1999, vol. 18, # 2, p. 291 - 305
[2] Patent: CN106748840, 2017, A. Location in patent: Paragraph 0020; 0021; 0022; 0023; 0024; 0025
[3] Justus Liebigs Annalen der Chemie, 1870, vol. 153, p. 285
[4] Journal fuer Praktische Chemie (Leipzig), 1882, vol. <2> 25, p. 491
[5] Chemische Berichte, 1917, vol. 50, p. 448
