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Benzotriazole
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Benzotriazole
Benzotriazole (BTA) is a heterocyclic compound with the chemical formula C6H4N3H. It can be viewed as the fusion of a benzene and triazole rings. It is a white solid, although impure samples can appear tan. It is used as a corrosion inhibitor for copper and silver.
Benzotriazole features two fused rings. It can in principle exist as tautomers, but X-ray crystallography establishes the structure with hydrogen at the 1 position. The N=N and HN−N distances are 1.306 Å and 1.340 Å.
Benzotriazole can be prepared by the reaction of o-phenylenediamine with a mixture sodium nitrite and acetic acid (a portion of this reaction mechanism is shown below):
BTA is a weak Bronsted acid with a pKa = 8.2. It is a weak Brønsted base, as indicated by the low pKa < 0 of its conjugate acid, [HBTA]+.
It is also a Lewis base, binding Lewis acids at the C−N=N center. A variety coordination complexes are known such as the tetrahedral 2:1 derivative with zinc chloride, ZnCl2(BTA)2. In some complexes, BTA binds metals as its conjugate base forming polymers and oligomers. It binds to copper surfaces, serving as a corrosion inhibitor.
Deprotonation of BTA followed by treatment with alkyl halides gives a mixture of 1- and 2-alkyl derivatives. Aromatic aldehydes (ArCHO) in the presence of ethanol gives benzotriazole-based N,O-acetals:
These acetals are susceptible to deprotonation, giving access to acylsilanes and acylboranes.
N-amination of BTA with hydroxylamine-O-sulfonic acid gives 1-aminobenzotriazole. Oxidation of this amine with lead(IV) acetate affords benzyne, which rapidly dimerises to biphenylene.
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Benzotriazole
Benzotriazole (BTA) is a heterocyclic compound with the chemical formula C6H4N3H. It can be viewed as the fusion of a benzene and triazole rings. It is a white solid, although impure samples can appear tan. It is used as a corrosion inhibitor for copper and silver.
Benzotriazole features two fused rings. It can in principle exist as tautomers, but X-ray crystallography establishes the structure with hydrogen at the 1 position. The N=N and HN−N distances are 1.306 Å and 1.340 Å.
Benzotriazole can be prepared by the reaction of o-phenylenediamine with a mixture sodium nitrite and acetic acid (a portion of this reaction mechanism is shown below):
BTA is a weak Bronsted acid with a pKa = 8.2. It is a weak Brønsted base, as indicated by the low pKa < 0 of its conjugate acid, [HBTA]+.
It is also a Lewis base, binding Lewis acids at the C−N=N center. A variety coordination complexes are known such as the tetrahedral 2:1 derivative with zinc chloride, ZnCl2(BTA)2. In some complexes, BTA binds metals as its conjugate base forming polymers and oligomers. It binds to copper surfaces, serving as a corrosion inhibitor.
Deprotonation of BTA followed by treatment with alkyl halides gives a mixture of 1- and 2-alkyl derivatives. Aromatic aldehydes (ArCHO) in the presence of ethanol gives benzotriazole-based N,O-acetals:
These acetals are susceptible to deprotonation, giving access to acylsilanes and acylboranes.
N-amination of BTA with hydroxylamine-O-sulfonic acid gives 1-aminobenzotriazole. Oxidation of this amine with lead(IV) acetate affords benzyne, which rapidly dimerises to biphenylene.
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