Chemical Properties
Yellow crystalline powder
Uses
2-Amino-3,5-dibromobenzaldehyde may be employed in the preparation of tetradentate Schiff base ligands, via condensation with aliphatic diamines. These ligands forms nickel (II) and oxovanadium(IV) complexes.
Uses
2-Amino-3,5-dibromobenzaldehyde is a reagent used in the preparation of Ambroxol and Bromhexine (B678600) metabolites.
General Description
2-Amino-3,5-dibromobenzaldehyde has been identified as one of the oxidation product of bromhexine by controlled potential electrolysis followed by HPLC-UV and GC-MS. It participates in the Friedlnder condensation of C-βglycosylic ketones to form 2-substituted quinoline derivatives.
Synthesis
(1) Mix ethanol, water and o-aminobenzaldehyde with stirring at a molar ratio of 4:1:0.2. Elevate the temperature until the solid o-aminobenzaldehyde was completely dissolved; (2) add reduced iron powder, add 3 to 5 drops of hydrochloric acid, stir thoroughly, continue to elevate the temperature until the reaction system reached the reflux temperature, keep stirring the reaction, and monitor the progress of the reaction using high-performance liquid chromatography (HPLC); (3) after completion of the reaction, the reaction solution was filtered, and a mixture of bromine, potassium bromide, and water was added slowly to the filtrate by dropwise addition, and after completion of the dropwise addition, the Maintain the temperature and continue to stir the reaction; (4) add an excess of saturated sodium bicarbonate solution to the reaction mixture, stir well, precipitate a solid, and filter to obtain 2-amino-3,5-dibromobenzaldehyde. In this embodiment, the molar ratio of o-aminobenzaldehyde, bromine and potassium bromide was 1:1.93:9.5. The yield of 2-amino-3,5-dibromobenzaldehyde was 91.1% and the purity was 99.4%.
References
[1] Patent: CN107488121, 2017, A. Location in patent: Paragraph 0017; 0018; 0019; 0020-0023; 0025-0030; 0032-0037
[2] Patent: CN107488124, 2017, A. Location in patent: Paragraph 0018; 0019; 0020; 0021; 0022; 0023; 0024-0038
[3] Australian Journal of Chemistry, 1980, vol. 33, # 1, p. 91 - 99
[4] Patent: CN107488126, 2017, A. Location in patent: Paragraph 0018-0024; 0027-0031; 0034-0038
[5] Chemische Berichte, 1901, vol. 34, p. 1338
