Biotransformation of 3,5-dibromo-4-hydroxybenzonitrile under denitrifying, Fe(III)-reducing, sulfidogenic, and methanogenic conditions was written by Knight, Victoria K.;Berman, Mitchell H.;Haggblom, Max M.. And the article was included in Environmental Toxicology and Chemistry in 2003.Formula: C7H4BrNO This article mentions the following:
Bromoxynil (3,5-dibromo-4-hydroxybenzonitrile) is a halogenated aromatic nitrile herbicide used on a variety of crops for the postemergence control of annual broad-leaved weeds. The anaerobic biodegradability of bromoxynil and its aerobic transformation product, 3,5-dibromo-4-hydroxybenzoate, were examined in enrichment cultures established with anaerobic sediment under denitrifying, Fe(III)-reducing, sulfidogenic, and methanogenic conditions. Bromoxynil (100μM) was depleted in 20-30 days in the methanogenic, sulfidogenic, and Fe(III)-reducing enrichments but was stable under denitrifying conditions. The 3,5-dibromo-4-hydroxybenzoate (100μM) was depleted within 20-35 days under all 4 anaerobic conditions. Both compounds were stable in sterile controls. Bromoxynil and 3,5-dibromo-4-hydroxybenzoate were readily utilized upon respiking of the cultures. During utilization of bromoxynil, stoichiometric release of bromide was observed with transient accumulation of metabolites identified as bromocyanophenol, cyanophenol, and phenol. Bromoxynil heptanoate and octanoate were rapidly hydrolyzed to bromoxynil, which was further degraded. These results indicate that bromoxynil and 3,5-dibromo-4-hydroxybenzoate are degraded under different anaerobic conditions. Anaerobic degradation of bromoxynil proceeds via reductive debromination to 4-cyanophenol, which is further transformed to phenol and can ultimately be degraded to carbon dioxide. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4Formula: C7H4BrNO).
2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Formula: C7H4BrNO
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts