4-Bromo-2-nitrophenol

4-bromo-2-nitrophenol is an essential intermediate for fine chemical engineering. It can be used to synthesize derivatives with biological activity, such as heterocyclic compounds as peptidase inhibitors for treating diabetes, introducing fluorine-containing groups as pesticides, and aminic compounds as Btk inhibitors for treating immune diseases.

yellow crystalline powder or crystals

4-Bromo-2-nitrophenol serves as a precursor for synthesizing ether derivatives. It reacts with 1,2-dibromoethane in the presence of NaOH to form 4-bromo-1-(2-bromoethoxy)-2-nitrobenzene, and couples with 1-(2-bromoethoxy)-2-nitrobenzene using K2CO3 in DMF to yield 4-bromo-2-nitro-1-[2-(2-nitrophenoxy)ethoxy]benzene[1-2].

The Journal of Organic Chemistry, 32, p. 300, 1967 DOI: 10.1021/jo01288a012
Synthesis, p. 287, 1989

The Suzuki coupling of 4-bromo-2-nitrophenol with boronic acid was studied.

The synthesis method of 4-bromo-2-nitrophenol comprises the following steps: preparing nitric acid with a concentration of 7-8 M; dissolving p-bromophenol in dichloroethane to obtain a substrate with a concentration of 1.8-2.2 M; injecting the nitric acid and the substrate into a continuous flow reactor through two pumps respectively, mixing, controlling the temperature at 55-75°C, the reaction pressure at 0.35-0.45 MPa, and reacting for 20-30 min.

[1] Chreim, Leonardo. (2017). BAPTA and its bromo-derivative as calcium chelating agent useful in optical imaging. https://doi.org/10.13140/RG.2.2.33380.32644
[2] Huang, W., Yu, H., Sheng, R., Li, J., Hu, Y. (2008). Identification of pharmacophore model, synthesis and biological evaluation of N-phenyl-1-arylamide and N-phenylbenzenesulfonamide derivatives as BACE 1 inhibitors. Bioorganic & Medicinal Chemistry, 16(24), 10190–10197. https://doi.org/10.1016/j.bmc.2008.10.059