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Aziminobenzene is a heterocyclic compound widely known for its powerful corrosion-inhibiting properties, especially for copper and its alloys.
Aziminobenzene forms a thin, protective layer on metal surfaces by strongly binding to the metal, preventing oxidation and degradation in harsh environments.
Aziminobenzene is extensively used in industries such as electronics, automotive, and metallurgy, as well as in coolants, lubricants, and polymer stabilization.
CAS Number: 95-14-7
EC Number: 202-394-1
Chemical Formula: C6H5N3
Molecular Weight: 119.12
Synonyms: 1H-Benzotriazole, Benzotriazole, 95-14-7, 1,2,3-BENZOTRIAZOLE, 1H-Benzo[d][1,2,3]triazole, 2H-Benzotriazole, Azimidobenzene, 1H-1,2,3-Benzotriazole, Aziminobenzene, Benztriazole, Benzisotriazole, Benzene azimide, Cobratec #99, 2,3-Diazaindole, 1,2-Aminoazophenylene, 273-02-9, 1,2,3-Triazaindene, Pseudoazimidobenzene, 2H-benzo[d][1,2,3]triazole, Cobratec 99, 1,2,-Aminozophenylene, 1,2,3-Triaza-1H-indene, Cobratec 35G, NSC-3058, 1,2,3-1h-benzotriazole, Verzone Crystal, NCI-C03521, Kemitec TT, Rusmin R, Seetec BT, 27556-51-0, CCRIS 78, DTXSID6020147, U-6233, CHEBI: 75331, HSDB 4143, EINECS 202-394-1, MFCD00005699, UNII-86110UXM5Y, BRN 0112133, AI3-15984, 86110UXM5Y, DTXCID00147, EC 202-394-1, 4-26-00-00093 (Beilstein Handbook Reference), 1H-Benzotriazol, Benzotriazole (VAN), Entek, BtaH, CAS-95-14-7, Irgastab I 489, 1,2,3-Benzotriazole,1H-benzo[d][1,2,3]triazole, azaindazole, benzotriazol, ISK 3, aza-indazole, 3uzj, 1 h-benzotriazole, 1,3-Triazaindene, 0CT, 1,3-Benzotriazole, Cobratec No. 99, 1,2-Aminozophenylene, 1,2,3-Benztriazole, 1H-1,3-Benzotriazole, 1,3-Triaza-1H-indene, 1H-Benzotriazole (VAN8C, WLN: T56 BMNNJ, SCHEMBL8956, 1H-BT, MLS002302971, CHEMBL84963, 1H-benzo-[1,2,3]triazole, D 32-108, 1H-BENZOTRIAZOLE [MI], BDBM36293, NSC3058, Benzotriazole, analytical standard, HMS3091M10, Benzotriazole, reagent grade, 97%, CS-D1407, HY-Y0688, STR01561, Tox21_201501, Tox21_302934, BDBM50234613, MSK159039, STL281967, Benzotriazole, ReagentPlus(R), 99%, 1,2,3-BENZOTRIAZOLE [HSDB], 1H-Benzotriazole, >=98.0% (N), AKOS000119181, AKOS025396849, FB01299, PS-3644, NCGC00091322-01, NCGC00091322-02, NCGC00091322-03, NCGC00256574-01, NCGC00259052-01, BP-21454, SMR001252218, 1ST159039, DB-022595, MSK159039-1000, B0094, NS00010261, Benzotriazole, Vetec(TM) reagent grade, 98%, EN300-17964, Benzotriazole Solution in Toluene, 1000?g/mL, Benzotriazole Solution in Toluene, 1000mug/mL, D77352, G85866, AB00374479-06, 1ST159039-1000, AC-907/34124039, Q220672, Z57127352, F2190-0645, InChI=1/C6H5N3/c1-2-4-6-5(3-1)7-9-8-6/h1-4H,(H,7,8,9, 202-394-
Aziminobenzene is slightly soluble in water, soluble in hot water, and easily soluble in alkaline aqueous solutions.
Aziminobenzene is divided into oil-soluble benzotriazole and water-soluble benzotriazole.
Among them, water-soluble Aziminobenzene can be dissolved in water.
Aziminobenzene can also be dissolved with a solvent.
The high content of active components and the small number of impurities are prerequisites for the solubility of Aziminobenzene.
Aziminobenzene includes ethanol, benzene, toluene, chloroform, and N N-dimethylformamide.
The solubility of water and oil determines that Aziminobenzene must have a high content of impurities and less water to achieve both water and oil.
Aziminobenzene is not only water-soluble but also oil soluble.
Aziminobenzene, The emulsifier is not required for the addition process.
This can greatly reduce the side effects of the addition of Aziminobenzene.
Aziminobenzene is bitter, odorless, boiling point is 204℃ (15mmHg),soluble in alcohol, benzene, toluene, chloroform and dimethylformamide, and slightly soluble in water.
Aziminobenzene belong to the most effective corrosion inhibitors for copper and copper alloys.
Aziminobenzene does further show positive effects in protection of steel, gray iron, cadmium and nickel.
Aziminobenzene is one of the most effective corrosion inhibitors for copper and copper alloy used in various industries.
Further positive effects of Aziminobenzene can be seen in protection of steel, grey iron, Cadmium and Nickel.
Aziminobenzene is bitter, odorless, boiling point is 204℃ (15mmHg),soluble in alcohol, benzene, toluene, chloroform and dimethylformamide, and slightly soluble in water.
Aziminobenzene is a heterocyclic compound with the chemical formula C6H5N3.
Aziminobenzene's five-membered ring contains three consecutive nitrogen atoms.
Aziminobenzene may be viewed as fused rings of the aromatic compounds benzene and triazole.
Aziminobenzene has a variety of uses, for instance, as a corrosion inhibitor for copper.
Aziminobenzene is bitter,odorless,boiling point is 204℃(15mmHg),soluble in alcohol, benzene, toluene, chloroform and dimethylformamide,and slightly soluble in water.
Aziminobenzene is white to light yellow needles, m.p. 98.5 deg.] C, boiling point 204 ℃ (15 mm Hg), slightly soluble in water, soluble in alcohol, benzene, toluene, chloroform and other organic solvents.
Aziminobenzene copper corrosion inhibitor can be adsorbed on the metal surface to form a thin film to protect copper and other metals from corrosion and atmospheric harmful media.
Aziminobenzene can be absorbed on metal surface and form a thin film to protect copper and other metals.
Aziminobenzene is White needle, flake, granular, powder.
Aziminobenzene is soluble in alcohol,benzene,toluene,chloroform and DMF, slightly soluble in water,turn red in air with oxidation,explosive in vacuum distillation.
Aziminobenzene 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 Aziminobenzene, 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.
Aziminobenzene is used in protection, especially in the treatment of bronze disease.
The precise nature of the copper-Aziminobenzene complex is controversial, and many suggestions have been put forward.
Aziminobenzene derivatives have chemical and biological properties that are versatile in the pharmaceutical industry.
Aziminobenzene derivatives act as agonists for many proteins.
For example, vorozol and alizapride have beneficial inhibitory properties against different proteins, and Aziminobenzene 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.
Aziminobenzene can be processed into flakes, granules, powder.
Aziminobenzene is oxidized in the air and gradually turned red.
Aziminobenzene tastes bitter and odorless.
Aziminobenzene is soluble in ethanol, benzene, toluene, chloroform and N,N-dimethylformamide, slightly soluble in water.
Aziminobenzene is bitter, odorless, boiling point is 204% (15mmHg),soluble in alcohol, benzene, toluene, chloroform and dimethylformamide, and slightly soluble in water.
Aziminobenzene is a heterocyclic compound containing three nitrogen atoms, with the chemical formula C6H5N3.
Aziminobenzene is colorless and polar and can be used in various fields.
Aziminobenzene other names 1H-Benzotriazole, is slightly soluble in water.
Aziminobenzene is a heterocyclic compound containing three nitrogen atoms with the chemical formula C6H5N3.
Aziminobenzene has two fused rings.
Aziminobenzene's 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.
Aziminobenzene is highly water-soluble, does not decompose immediately, and has a limited absorption tendency. Aziminobenzene is only partially removed in wastewater treatment plants, and a significant part reaches surface waters such as rivers and lakes.
Aziminobenzene exists as a white solid.
Aziminobenzene is a heterocyclic compound containing three nitrogen atoms, with the chemical formula C6H5N3.
Aziminobenzene is an anticorrosive chemical used primarily on copper, but also on iron, steel, cadmium, chromium, zinc.
Aziminobenzene can form covalent and coordinate-covalent linkages with metals, which prevent attack by corrosive agents.
Aziminobenzene is bitter, odorless, soluble in alcohol, benzene, toluene, chloroform and DMF, slightly soluble in water, turn red in air with oxidation.
The simplest member of the class of benzotriazoles that consists of a benzene nucleus fused to a 1H-1,2,3-triazole ring.
Aziminobenzene consists of benzene and a tri-azole ring.
The nitrogen atoms in the triazole ring form a bond between the copper, which inhibits the product.
Uses of Aziminobenzene:
Aziminobenzene is mainly used as antirust agent and corrosion inhibitor for metals.
Aziminobenzene is widely used in the antirust oil products such as gas phase corrosion inhibitor , in treating agent for recycling water ,in antifreeze for cars antifogging for photograph.
Aziminobenzene is used as stabilizer for macromolecular compound, growth regulator for plant, lubricant additive , ultraviolet absorbent etc.
Aziminobenzene can be used together with many kinds of scale inhibitors and bactericide and algaecide,and Aziminobenzene shows excellent anticorrosion effect in close recycling cooling water system.
Aziminobenzene is used in metal rust and corrosion inhibitors, used in the preparation of water quality stabilizers, anti-rust greases, and also used in the synthesis of photographic anti-fogging agents and vapor phase rust inhibitors.
Aziminobenzene is used in extreme pressure industrial gear oils.
Aziminobenzene can be used as anti-rust and vapor phase corrosion inhibitor in lubricating grease such as curve gear oil, anti-wear hydraulic oil, oil film bearing oil, lubricating grease.
Aziminobenzene is used in anti-rust oil (grease) products, mostly used in the vapor phase of copper and copper alloy Corrosion inhibitor circulating water treatment agent, automobile antifreeze, photographic antifogging agent, polymer stabilizer, plant growth regulator, lubricant additive, ultraviolet absorber, etc.
Aziminobenzene can also be used in conjunction with a variety of scale inhibitors, bactericidal and algaecide.
Aziminobenzene is used for corrosion and rust prevention of copper and silver equipment.
Aziminobenzene can also be used in the preparation of photographic dust-proof, anti-fog and vapor phase rust inhibitor.
Aziminobenzene is mainly used as rust-preventer,antifreezing liquid, antioxidant additive(including lubricating oil, hydraulic oil,brake oil, transformer's oil), emugent, water stabilizer, the additive for high molecular materials'(polyester and polyesteramide)capacity of ultraviolet resistance and anstatic electricity, photographic antifogging agent, copper mine flotation, metal's slow corrosion etc.
Aziminobenzene has already been used as a restrainer (or anti-fogging agent) in photographic emulsions or developing solutions, and as a reagent for the analytical determination of silver.
Aziminobenzene has been extensively used as a corrosion inhibitor in the atmosphere and underwater.
Aziminobenzene's derivatives and their effectiveness as drug precursors have been drawing attention.
Aziminobenzene can be used as antifreezes, heating and cooling systems, hydraulic fluids, and vapor-phase inhibitors as well.
Aziminobenzene is an effective corrosion inhibitor for copper and its alloys by preventing undesirable surface reactions.
Aziminobenzene is known that a passive layer, consisting of a complex between copper and benzotriazole, is formed when copper is immersed in a solution containing benzotriazole.
Aziminobenzene is used in conservation, notably for the treatment of bronze disease.
Aziminobenzene derivatives act as agonists for many proteins.
For instance, vorozole and alizapride have useful inhibitory properties against different proteins and benzotriazole esters have been reported to work as mechanism-based inactivators for severe acute respiratory syndrome (SARS) 3CL protease.
The methodology is not only limited to heterocyclization but was also successful for polynuclear hydrocarbons of small carbocyclic systems.
Environmental relevance:
Aziminobenzene is fairly water-soluble, not readily degradable and has a limited sorption tendency.
Hence, Aziminobenzene is only partly removed in wastewater treatment plants and a substantial fraction reaches surface water such as rivers and lakes.
Aziminobenzene is considered to be of low toxicity and a low health hazard to humans although exhibiting some antiestrogenic properties.
Aziminobenzene is mainly used as rust-preventer, antifreezing liquid, antioxidant additive(including lubricating oil, hydraulic oil, brake oil, transformer's oil), emugent, water stabilizer, the additive for high molecular materials' (polyester and polyesteramide) capacity of ultraviolet resistance and anti- static electricity, photographic antifogging agent, copper mine flotation, metal's slow corrosion etc.
Aziminobenzene is used Cooling water systems / industrial water treatment, industrial lubricants (e.g. drilling and cutting fluids), dishwashing tablets (silver protection), metal detergents and polishing, coolants, VCI papers / metal packaging, antifogging agent (photo)
Aziminobenzene is used in cooling water or boiler systems by the industrial water treatment industry.
Aziminobenzene can be also used in coolants and antifreeze products.
An application of Aziminobenzene is the use as an additive in industrial lubricants, like e.g. drilling and cutting fluids.
Aziminobenzene does also work to protect silver ware in dishwashing tablets and can be further used in metal detergents.
Aziminobenzene is mainly used as rust-preventer, antifreezing liquid, antioxidant additive(including lubricating oil, hydraulic oil, brake oil, transformer's oil), emugent, water stabilizer, the additive for high molecular materials (polyester and polyesteramide) capacity of ultraviolet resistance and anti-static electricity, photographic antifogging agent, copper mine flotation, metal's slow corrosion etc.
Aziminobenzene is used in combination with ammonium hydroxide and ethylenediaminetetraacetic acid.
Aziminobenzene has an anti-corrosion effect on metal materials such as copper, aluminum, cast iron, nickel, and zinc.
Aziminobenzene can be combined with a variety of corrosion inhibitors to improve corrosion inhibition.
Aziminobenzene is also widely used in metal rust inhibitors such as copper, silver, zinc, aluminum, cast iron, water purifying agents, etc.
Aziminobenzene is mainly used for water treatment, oil oxidation, metal oxidation and so on.
Aziminobenzene has a good corrosion inhibition effect on the copper and has the same anti-corrosion effect on other metal materials.
Aziminobenzene is also preferred UV absorber.
Adding benzotriazole to products such as plastics, rubber, and fuel can solve the degradation problem well.
And Aziminobenzene can improve the light resistance of synthetic materials.
Aziminobenzene is used for surface purification of silver, copper, and zinc in electroplating, and has an anti-tarnishing effect.
Aziminobenzene is a good ultraviolet light absorber and can be used as a development antifogging for black and white film and photographic paper.
Aziminobenzene is used additive to cutting fluid, immobile working fluid, antifreeze, circulating coolant, etc.
When added to lubricating oil and transformer oil, Aziminobenzene prevents aging of the oil.
Aziminobenzene is used additive for acidic copper plating solution.
When added to coating agents such as paints, Aziminobenzene inhibits corrosion of the underlying film.
Aziminobenzene is used additives for copper polishing agents.
In the photographic industry, Aziminobenzene is used as a stabilizer against ultraviolet lights.
Aziminobenzene has already been used as a restrainer in photographic emulsions and as a reagent for the analytical determination of silver.
Aziminobenzene has been extensively used as a corrosion inhibitor in the atmosphere and underwater.
Aziminobenzene can be used as antifreezes, heating and cooling systems, hydraulic fluids and vapor phase inhibitors as well.
Aziminobenzene is an effective corrosion inhibitor for copper and its alloys by preventing undesirable surface reactions.
Aziminobenzene is used in conservation, notably for the treatment of bronze disease.
Aziminobenzene is used Photographic emulsions, anti-corrosion, pharmaceutical industry.
Aziminobenzene 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.
Aziminobenzene has been widely used as a corrosion inhibitor in the atmosphere and underwater.
Aziminobenzene is used in antifreeze, heating and cooling systems, hydraulic fluids and vapor phase inhibitors.
Aziminobenzene is mainly used as rust-preventer, anti-freezing liquid, antioxidant additive(including lubricating oil, hydraulic oil, brake oil, transformer's oil), water stabilizer, the additive for high molecular materials (polyester and polyesteramide) capacity of ultraviolet resistance and anti-static electricity, photographic anti-fogging agent, copper mine flotation, metal's slow corrosion etc.
Aziminobenzene is applied as anti-rusting agent or corrosion inhibitor for metal (mainly copper and its alloys) by forming a passive layer, consisting of a complex between copper and benzotriazole, when copper is immersed in a solution containing benzotriazole.
Aziminobenzene is used as anti-freezing agent for car, synthetic detergent, anti-dust agent for photography and polymer stabilizer.
Aziminobenzene is mainly used as rust-preventer, antifreezing liquid, (including lubricating oil, hydraulic oil, brake oil, transformer's oil), emugent, water stabilizer, the additive for high molecular materials (polyester and polyesteramide) capacity of ultraviolet resistance and anti static electricity, photographic antifogging agent, copper mine flotation, metal's slow corrosion etc.
Aziminobenzene is a corrosion inhibitor for copper and copper alloys, and is commonly used in water cooling systems.
Aziminobenzene applications include use as a silver polishing agent in dishwasher detergent, automotive antifreeze, antirust for photography, and use as a lubricant additive.
Aziminobenzene can also be derived to create anti-fading agents for metals, antiseptic agents, UV-absorbers, pesticides, and photoconductors.
Aziminobenzene also possesses antihypertensive, antibacterial, analgesic, antifungal, antiviral, and anti-inflammatory properties.
Aziminobenzene is an anticorrosive agent well known for its use in aircraft deicing and antifreeze fluids but also used in dishwasher detergents.
Aziminobenzene on copper, aluminum, cast iron, nickel, zinc and other metal materials have anti-corrosion effect.
It can be combined with a variety of corrosion inhibitors, such as with chromate, polymeric phosphate, molybdate, silicate, nitrite, ATMP, HEDP, EDTMP, etc.
Aziminobenzene can improve the corrosion inhibition effect.
Aziminobenzene can be used with a variety of scale inhibitors, bactericidal algaecide, benzotriazole on the corrosion inhibition of polyphosphate does not interfere, the oxidation resistance is very strong.
Aziminobenzene is used in anti-rust oil (Grease) products, mostly used in copper and copper alloy vapor phase corrosion inhibitor circulating water treatment agent, automobile antifreeze, photographic antifogging agent, polymer stabilizer, plant growth regulator, lubricating oil additive, ultraviolet absorber, etc.
Aziminobenzene can also be used in combination with a variety of scale inhibitors and biocide.
Aziminobenzene is mainly used for metal (such as silver, copper, lead, zinc, nickel) as antirust and corrosion inhibitor.
Aziminobenzene is widely used in rustproof oil (fat) products, and more as vapor phase inhibitors of copper and copper alloy, circulating water treatment agent, also used for auto antifreeze, polymer stabilizers, plant growth regulator, lubricant additives, UV absorber, etc, and used for garment/hair dying and pharmaceutical chemical.
Aziminobenzene can also be matched with a variety of scale inhibitor, algae fungicidal, especially has good corrosion-resistant effect on closed circulating cooling water system.
Aziminobenzene is mainly used as antirust agent and corrosion inhibitor for metals.
Aziminobenzene is widely used in the antirust oil products such as gas phase corrosion inhibitor, in treating agent for recycling water, in antifreeze for cars antifogging for photograph, also used as stabilizer for macromolecular compound growth regulator for plant, lubricant additive, ultraviolet absorbent etc.
Aziminobenzene can be used together with many kind of scale inhibitors and bactericide algaecide, show excellent anticorrosion effect in close recycling cooling water system.
Aziminobenzene is mainly used as rust-preventer, antifreezing liquid, antioxidant additive(including lubricating oil, hydraulic oil, brake oil, transformer's oil), emugent, water stabilizer, the additive for high molecular materials (polyester and polyesteramide) capacity of ultraviolet resistance and anti static electricity, photographic antifogging agent, copper mine flotation, metal's slow corrosion etc.
As an anticorrosive, Aziminobenzene is used in metal working, in art restoration, and in the construction industry as a tarnish remover and a protective coating.
Aziminobenzene functions as a corrosion inhibitor in water cooling systems and in dry cleaning equipment.
Aziminobenzene is used in synthetic greases, lubricants, and hydraulic fluids to prevent the oxidation of these materials which is catalyzed by metal ions.
In the electronics industry, Aziminobenzene is used to treat packing materials for copper electronic parts and to extend the life of polymers that are used as insulators for copper wire
Aziminobenzene is used in electrolytic processing, where the stripping of metals from copper cathodes is eased by pretreatment of the cathode with BTA.
In photographic processing, Aziminobenzene acts as an antifogging agent in silver-halide emulsions, restraining the developer and preventing the blackening or fogging of the image due to overdevelopment.
Aziminobenzene is mainly used as antirust or corrosion inhibitors for copper or copper alloy etc in lubricant oil/grease, circulating water treatment, engine coolant etc. also used with antiscale additives
Aziminobenzene is mainly used in the metal's (silver, lead, nickel, zinc, copper) antirust and corrosion moderating, widely used in antirust oil, copper and alloy copper's moderating corrosion, water circulation treatment, antifogging agent, macromolecule stabilizer, plant growth regulator, lubricating oil additive, ultraviolet absorber etc.
Aziminobenzene also can cooperate with many kinds of dirt prevention and germs killing, especially and household detergent to the corrosion.
Aziminobenzene is a very widely used chemical in various industries.
Aziminobenzene is used as a corrosion inhibitor for metals such as copper and its alloys.
Aziminobenzene is used as anti blur factor in photo printing.
Aziminobenzene is used in production of light-sensitive chemicals.
Aziminobenzene is used in application in cleaners used in plating processes.
Aziminobenzene is used in production Water purification products and Laboratory chemicals.
Aziminobenzene Corrosion Inhibitor:
One of the most common methods of corrosion control is the use of disinfectants such as nitrates and chromates.
Finding alternative compounds for these compounds is very important for environmental reasons.
Aziminobenzene and the azole family are one of these alternatives, which chemically adsorb nitrogen atoms on the surface by sharing unpaired electron pairs with an empty metal orbital to prevent dissolution and corrosion.
Aziminobenzene is mainly used as rust-preventer, antifreezing liquid, antioxidant additive (including lubricating oil, hydraulic oil, brake oil, transformer's oil), emugent, water stabilizer, the additive for high molecular materials (polyester and polyesteramide) capacity of ultraviolet resistance and anti- static electricity, photographic antifogging agent, copper mine flotation, metal's slow corrosion etc.
Aziminobenzene is a chemical used as a ligand to form complexes and has many applications in industry, the most common of which is to prevent rust and corrosion of metals.
Aziminobenzene is a corrosion inhibitor for metals such as copper and its alloys, silver, aluminum, cobalt, and zinc, which are relatively soluble in water and do not decompose easily.
Aziminobenzene, commonly abbreviated as BTA, is a versatile compound used in industries such as Semiconductor/Electronic manufacturing and drug manufacturing.
Aziminobenzene in solution allows the material to react with certain metals to create a corrosion inhibiting layer.
For this reason, Aziminobenzene is also a common component in materials such as antifreeze or detergents, where metal corrosion is a concern.
Benefits of Aziminobenzene:
Aziminobenzene is a corrosion inhibitor for copper, copper alloys, and other metals.
Forming rust preventive firm of Aziminobenzene is thin, insoluble, and transparent.
Stable for an acid and an alkaline.
Absorbs ultraviolet lights.
Soluble with various solvent.
Preparation Method of Aziminobenzene:
Aziminobenzene is obtained by reacting o-benzenetriamine with sodium nitrite.
The o-benzenetriamine was dissolved in 50°C water, and then glacial acetic acid was added to cool to 5°C.
The reaction was then stirred by the addition of sodium nitrite.
The reactants gradually turned dark green.
The temperature rose to 70-80°C and the solution turned orange.
Leave at room temperature for 2 h.
The crystals were cooled, filtered, washed with ice water and dried to dryness.
The crude product was distilled under reduced pressure.
The fraction of 201-204°C (2.0 kPa) was collected and recrystallized from benzene to obtain a product having a melting point of 96°C-97°C, and the yield was about 80%.
Aziminobenzene is synthesized from the reaction between orthophenylenediamine, sodium nitrite, and acetic acid.
To improve the reaction, it is done at temperatures of 5 to 10 degrees and in an ultrasonic bath.
Structure of Aziminobenzene:
Aziminobenzene features two fused rings.
Aziminobenzene's five-membered ring can exist in tautomers A and B, and the derivatives of both tautomers, structures C and D, can also be produced:
Benzotriazole tautomers and their derivatives.
Various structural analyses with UV, IR and 1H-NMR spectra indicated that isomer A is predominantly present at room temperature.
The bond between positions 1 and 2 and the one between positions 2 and 3 have proved to have the same bond properties.
Moreover, the proton does not tightly bind to any of the nitrogen atoms, but rather migrates rapidly between positions 1 and 3.
Therefore, the Aziminobenzene can lose a proton to act as a weak acid (pKa = 8.2) or accept a proton using the lone pair electrons located on its nitrogen atoms as a very weak Brønsted base (pKa < 0).
Not only can Aziminobenzene act either as an acid or base, Aziminobenzene can also bind to other species, utilizing the lone pair electrons.
Applying this property, the Aziminobenzene can form a stable coordination compound on a copper surface and behave as a corrosion inhibitor.
Aziminobenzene is a heterocycle compound with the chemical formula C6H5N3.
Aziminobenzene has two nitrogen rings in its chemical structure which are produced by the fusion of the benzene ring, this point causes the stability and resistance of the molecule.
Aziminobenzene consists of two five-membered rings that include tautomers A and B, and derivatives of both tautomers can form structures C and D.
Synthesis and Reactions of Aziminobenzene:
A synthesis of the Aziminobenzene involves the reaction of o-phenylenediamine, sodium nitrite, and acetic acid.
The conversion proceeds via diazotization of one of the amine groups:
The synthesis can be improved when the reaction is carried out at low temperatures (5–10 °C) and briefly irradiated in an ultrasonic bath.
Typical batch purity is 98.5% or greater.
Biphenylene and benzyne can be conveniently prepared from benzotriazole by N-amination with hydroxylamine-O-sulfonic acid.
The major product, 1-aminobenzotriazole, forms benzyne in an almost quantitative yield by oxidation with lead(IV) acetate, which rapidly dimerises to biphenylene in good yields.
History of Aziminobenzene:
Aziminobenzene was first synthesized in the late 19th century during studies on nitrogen-rich heterocycles, primarily through the reaction of o-phenylenediamine with nitrous acid.
Initially, it attracted limited attention, but its ability to form stable complexes with metals, especially copper, soon highlighted its value as a corrosion inhibitor.
By the 1950s, BTA had gained significant industrial importance, particularly in the protection of copper and its alloys in cooling systems, antifreeze solutions, and industrial lubricants.
Throughout the 1960s and 1970s, its applications expanded to electronics, automotive industries, and as an additive in engine coolants.
In the following decades, BTA also found uses as a UV stabilizer in polymers, a photographic chemical, and a passivation agent in metallurgy.
Today, it remains a key compound in metal protection, although recent research has focused on developing environmentally friendly alternatives due to concerns about its persistence and toxicity in aquatic environments.
Handling and Storage of Aziminobenzene:
Handling:
Avoid contact with skin, eyes, and clothing.
Prevent inhalation of dust, vapors, or fumes.
Use only in well-ventilated areas or under fume hoods.
Avoid generating dust; handle with proper protective equipment.
Do not eat, drink, or smoke while handling this chemical.
Storage:
Store in a tightly sealed container.
Keep in a cool, dry, and well-ventilated area.
Protect from heat, open flames, and direct sunlight.
Store away from oxidizing agents, strong acids, and bases.
Reactivity and Stability of Aziminobenzene:
Stability:
Stable under recommended storage conditions.
Reactivity:
May react with strong oxidizers.
Avoid contact with strong acids and alkalis.
Hazardous Decomposition Products:
When heated to decomposition, emits toxic fumes of nitrogen oxides (NOx).
Conditions to Avoid:
Excessive heat, open flames, and moisture.
First Aid Measures of Aziminobenzene:
Inhalation:
Move the person to fresh air.
If breathing is difficult, provide oxygen.
Seek medical attention if symptoms persist.
Skin Contact:
Wash affected area thoroughly with soap and water.
Remove contaminated clothing.
Seek medical help if irritation persists.
Eye Contact:
Rinse immediately with plenty of water for at least 15 minutes.
Seek medical attention if irritation continues.
Ingestion:
Rinse mouth with water.
Do not induce vomiting.
Seek medical advice immediately.
Firefighting Measures of Aziminobenzene:
Suitable Extinguishing Media:
Water spray, dry chemical, foam, or carbon dioxide (CO₂).
Unsuitable Media:
Do not use a high-volume water jet.
Fire Hazards:
May release toxic fumes (NOx) when burning.
Protective Equipment for Firefighters:
Use self-contained breathing apparatus (SCBA) and protective clothing.
Accidental Release Measures of Aziminobenzene:
Personal Precautions:
Wear protective gloves, safety goggles, and dust mask/respirator.
Avoid dust formation.
Environmental Precautions:
Prevent entry into drains, waterways, or soil.
Methods for Clean-Up:
Sweep or vacuum the material (avoid dry sweeping that raises dust).
Place in a properly labeled container for disposal.
Wash contaminated surfaces.
Exposure Controls / Personal Protection of Aziminobenzene:
Engineering Controls:
Use with local exhaust ventilation or in a chemical fume hood.
Personal Protective Equipment (PPE):
Eye Protection:
Chemical safety goggles.
Skin Protection:
Chemical-resistant gloves (nitrile or neoprene).
Body Protection:
Lab coat or protective clothing.
Respiratory Protection:
Use NIOSH-approved respirator if airborne concentrations exceed limits.
Hygiene Measures:
Wash hands and face after handling.
Remove contaminated clothing and wash before reuse.
Identifiers of Aziminobenzene:
CAS Number: 95-14-7
EC Number: 202-394-1
UNII: J1J70VHG2F
PubChem CID: 7226
Molecular Formula: C₆H₅N₃
Molecular Weight: 119.12 g/mol
InChI: InChI=1S/C6H5N3/c1-2-4-6-5(1)7-9-8-6/h1-4H,(H,7,8,9)
InChI Key: GEHQUJUHKYNOCV-UHFFFAOYSA-N
SMILES: c1ccc2c(c1)[nH]nn2
CAS Registry Number: 95-14-7
EC Number: 202-394-1
RTECS Number: DM1225000
Beilstein Reference: 146941
Merck Index: 13,1080
HS Code: 2933.99
UN Number: Not classified as dangerous goods for transport under UN.
Properties of Aziminobenzene:
Appearance: White to light yellow needle-shape crystalloids or granular
Purity, %: 99.5 min
Colour APHA (Hazen): 40.0 max
Moisture, %: 0.1 max
Melting point, ℃: 96.0 min
Ash content, %: 0.03 max
pH: 5.0-6.0
Molar mass: 119.127 g·mol−1
Appearance: White solid
Density: 1.36 g/mL
Melting point: 100 °C (212 °F; 373 K)
Boiling point: 350 °C (662 °F; 623 K)
Solubility in water: 20 g/L
Acidity (pKa): 8.2
Basicity (pKb): > 14
PSA: 41.57000
XLogP3: 1
Appearance: Aziminobenzene appears as white to light tan crystals or white powder. No odor.
Density: 1.36 g/cm3
Melting Point: 98.5 °C
Boiling Point: 159 °C @ Press: 2 Torr
Flash Point: 170ºC
Refractive Index: 1.715
Water Solubility: H2O: 25 g/l in water (20 ºC)
Vapor Pressure: 0.04 mm Hg ( 20 °C)
Vapor Density: 4.1 (vs air)
Odor: No odor
PH: The solution in water is a weak acid
Molecular Weight: 119.12
XLogP3: 1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Exact Mass: 119.048347172
Monoisotopic Mass: 119.048347172
Topological Polar Surface Area: 41.6
Heavy Atom Count: 9
Complexity: 92.5
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
