What is benzotriazole?
Benzotriazole (BTA) is a heterocyclic compound containing three nitrogen atoms with the chemical formula C6H5N3. This aromatic compound is colorless and polar and can be used in various fields. It is called BTA for short.
Benzotriazole has two fused rings. Its five-membered ring may be present in tautomers A and B, and derivatives of both tautomers as well as structures C and D can be produced.
Various structural analyzes with UV, IR and 1H-NMR spectra showed that isomer A is predominantly present at room temperature. The bond between positions 1 and 2 and between positions 2 and 3 has proven to have the same bond properties. Moreover, the proton is not tightly bound to any nitrogen atom but instead moves rapidly between positions 1 and 3. Therefore, BTA can lose a proton (pKa = 8.2) to behave as a weak acid, or a proton using the lone pair electrons found in nitrogen atoms as a very weak Bronsted base (pKa < 0). Not only can it act as an acid or a base, but it can also bind to other species using lone pair electrons. Applying this property, BTA can form a stable coordination compound on a copper surface and act as a corrosion inhibitor.
How is benzotriazole produced?
Benzotriazole is highly water-soluble, does not decompose immediately, and has a limited absorption tendency. Therefore, it is only partially removed in wastewater treatment plants, and a significant part reaches surface waters such as rivers and lakes. Although it exhibits some antiestrogenic properties, it is considered to have low toxicity and low health hazard to humans.
What does benzotriazole look like?
It exists as a white solid.
What is the molecular formula of benzotriazole?
Molecular Formula: C6H5N3
In which sectors is benzotriazole used?
- photographic emulsions
- pharmaceutical industry
What are the uses (processes) of benzotriazole?
- Benzotriazole is known for its versatility. It is already used as a limiting (or anti-fogging agent) in photographic emulsions or solution development, and as a reagent for the analytical determination of silver.
- It has been widely used as a corrosion inhibitor in the atmosphere and underwater.
- It is used in antifreeze, heating and cooling systems, hydraulic fluids and vapor phase inhibitors.
- Benzotriazole is an effective corrosion inhibitor for copper and its alloys by preventing undesirable surface reactions. It is known that when copper is immersed in a solution containing benzotriazole, a passive layer consisting of a complex between copper and benzotriazole is formed. The passive layer is insoluble in aqueous and many organic solutions. There is a positive relationship between the thickness of the passive layer and the effectiveness of preventing corrosion. BTA is used in protection, especially in the treatment of bronze disease. The precise nature of the copper-BTA complex is controversial, and many suggestions have been put forward.
- Benzotriazole derivatives have chemical and biological properties that are versatile in the pharmaceutical industry. Benzotriazole derivatives act as agonists for many proteins. For example, vorozol and alizapride have beneficial inhibitory properties against different proteins, and benzotriazole esters have been reported to work as mechanism-based inactivators for the severe acute respiratory syndrome (SARS)3CL protease. The methodology is not only limited to heterocyclization, but has also been successful for polynuclear hydrocarbons of small carbocyclic systems.
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