BTA (BENZOTRIAZOLE)

CAS Number : 95-14-7 
EC Number  : 202-394-1
PubChem CID : 7220
ECHA InfoCard : 100.002.177 
ChemSpider    : 6950 
Chemical formula :  C6H5N3
Molar mass     :  119.127 g·mol−1
Density             :  1.36 g/mL
Melting point     :  100 °C

Benzotriazole (BTA) is a heterocyclic compound with the chemical formula C6H5N3. 
Benzotriazole features a five-membered ring containing three nitrogen atoms. 
This white to light tan solid has a variety of uses, for instance, as a corrosion inhibitor for copper.

Synthesis and reactions of Benzotriazole
A synthesis of the BTA 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.

Applications of Benzotriazole
Benzotriazole has been known for its great versatility. 
Benzotriazole 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. More importantly, it has been extensively used as a corrosion inhibitor in the atmosphere and underwater. 
Also, Benzotriazoles derivatives and their effectiveness as drug precursors have been drawing attention. 
Besides all the applications mentioned above, the BTA can be used as antifreezes, heating and cooling systems, hydraulic fluids and vapor phase inhibitors as well.

Corrosion inhibitor
Benzotriazole is an effective corrosion inhibitor for copper and its alloys by preventing undesirable surface reactions. 
Benzotriazole 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. 
The passive layer is insoluble in aqueous and many organic solutions. 
There is a positive correlation between the thickness of the passive layer and the efficiency of preventing corrosion.
BTA is used in conservation, notably for the treatment of bronze disease. 
The exact structure of the copper-BTA complex is controversial and many proposals have been suggested.

Drug precursor
Benzotriazole derivatives have chemical and biological properties that are versatile in the pharmaceutical industry. 
Benzotriazole 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
Benzotriazole is fairly water-soluble, not readily degradable and has a limited sorption tendency. 
Hence, it is only partly removed in wastewater treatment plants and a substantial fraction reaches surface water such as rivers and lakes.
It is considered to be of low toxicity and a low health hazard to humans although exhibiting some antiestrogenic properties.

1,2,3-benzotriazole appears as white to light tan crystals or white powder.
Benzotriazole is the simplest member of the class of benzotriazoles that consists of a benzene nucleus fused to a 1H-1,2,3-triazole ring. 
It has a role as an environmental contaminant and a xenobiotic.

Use and Manufacturing of Benzotriazole
Used as an anti-corrosion agent and an anti-fogging agent in developing photographs; also used as a chemical intermediate; [HSDB] Being used less often as an anti-corrosion agent in metalworking fluids because it is a known skin sensitizer;

Its main use is as an anticorrosive in metalworking, in art restoration, and as a tarnish remover and protective coating in the construction industry. 
Benzotriazole is used as a corrosion inhibitor in water-cooling systems and in dry-cleaning equipment. 
Benzotriazole is also used in some formulations of automatic dishwasher detergents to prevent tarnishing of metal utensils.
Benzotriazole is used in other capacities in electrolytic and photographic processing.

Industry Uses of Benzotriazole
-Corrosion inhibitors and anti-scaling agents
-Laboratory chemicals
-Lubricants and lubricant additives
-Photosensitive chemicals
-Plating agents and surface treating agents
-electronics

Consumer Uses of Benzotriazole
-Electrical and electronic products
-Laundry and dishwashing products
-Lubricants and greases
-Metal products not covered elsewhere
-Photographic supplies, film, and photo chemicals
-Water treatment products
-laboratory chemicals
-used in product that is used as a cleaner in plating processes. The processes are diverse, examples of final use are automotive and machinery.

Household Products of Benzotriazole
Household & Commercial/Institutional Products
Information on 38 consumer products that contain Benzotriazole in the following categories is provided:
-Auto Products
-Inside the Home

General Manufacturing Information
-Industry Processing Sectors
-All other basic organic chemical manufacturing
-All other chemical product and preparation manufacturing
-Computer and electronic product manufacturing
-Electrical equipment, appliance, and component manufacturing
-Fabricated metal product manufacturing
-Miscellaneous manufacturing
-Oil and gas drilling, extraction, and support activities
-Petroleum lubricating oil and grease manufacturing
-Photographic film paper, plate, and chemical manufacturing
-Primary metal manufacturing
-Soap, cleaning compound, and toilet preparation manufacturing
-resale of chemicals

BTA is a good corrosion inhibitor. 
BTA is a bicyclic nitrogen-containing heterocyclic organic compound containing a benzene ring and a 1,2,3-triazole ring. 
In the process of multilayer copper interconnect CMP, BTA is widely used as an inhibitor. 
BTA can effectively reduce the corrosion of the copper surface and help flatten the wafer surface after CMP. 
However, it is flammable and poisonous. 
BTA can react with copper and produce Cu-BTA passivation, which requires a large mechanical force to remove and seriously affects the surface defects. 
On the other hand, under high pH conditions, its ability to correct the height difference is weakened.

As a corrosion inhibitor, Benzotriazole decreases the corrosion rate of metals and alloys. 
This works by forming a coating, a passivation layer, which prevents access of the corrosive substance to the metal or alloy underneath. 
This is of particular importance in industries where fluids routinely need to be in continuous contact with metals that require protection.
Benzotriazole shows outstanding thermic and oxidative stability and is also resistant to UV light. It does not negatively affect the appearance of the metal it's applied to.
Benzotriazole is very bright in color so that solutions – either aqueous or in different solvents – are clear and almost colorless. 
A table of solubility properties and max concentrations is available on request.

Grades available
-Granular
-Fine granular
-Flake
-Crystal

Benzotriazole can be used in different applications in major industries. 
For example, it is used in cooling water or boiler systems by the industrial water treatment industry. 
Benzotriazole can be also used in coolants and antifreeze products. 
Another application is the use as an additive in industrial lubricants, like e.g. drilling and cutting fluids. 
Benzotriazole does also work to protect silver ware in dishwashing tablets and can be further used in metal detergents.

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.

Benzotriazole is known for its versatility. 
Benzotriazole 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.
Benzotriazole has been widely used as a corrosion inhibitor in the atmosphere and underwater.
Benzotriazole 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. 

Benzotriazole 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.

Benzotriazole is used as a anticorrosive agent in cooling fluids fuels, photographic development, antifreeze, dry cleaning, art restoration; tarnish remover and protective coatings in construction industry.
Benzotriazole is used as a component of aircraft de-icing fluid, pickling inhibitor in boiler scale removal, restrainer, developer and antifogging agent in photographic emulsions, corrosion inhibitor for copper, chemical intermediate for dyes, in pharmaceuticals, and as fungicide.

Benzotriazole is a specific corrosion inhibitor for copper and copper alloys. 
Benzotriazole is now widely used in industry to reduce the corrosion of these alloys under both atmospheric and immersed conditions. 
Corrosion of copper may produce a surface stain or tarnish, pitting of surfaces of pipes or promote pitting of other metals, such as aluminium, which are in contact with dissolved copper in the water. 
Benzotriazole is used to reduce these forms of attack and the methods by which it is applied are discussed in this paper.

Benzotriazole (BtH) is particularly versatile synthetic auxiliary because of its attractive properties. 
Benzotriazole can be easily inserted into molecules and equally can also act as a good leaving group. 
This molecule is a weak acid (pKa 8.2) as well as weak base (pKa < 0) and because of this acid-base property of benzotriazole. 
This molecule also shows not only electron donating but also electron attracting ability, which leads to various synthetic applications. 
In 1980, benzotriazole was first reported as synthetic auxiliary in organic chemistry . 
Since then benzotriazole is used in the construction of various monocyclic and bicyclic heterocyclic compounds which are difficult to prepare by other methods.

Benzotriazole and its derivatives plays important role in various reactions like acylation, aroylation and substitution reactions . 
Substitution of hydroxyl group with chloride group of the sterically and electronically hindered alcohol of carbohydrates involves harsh reaction conditions and expensive reagents. 
Furthermore, the formation of halides from nucleofugal groups leads in the formation of unsaturated products and also chances of losing chirality due to harsh reaction condition. Saxena et. al. reported benzotriazole sulfonate (prepared in-situ from benzotriazole and thionylchloride)as potential reagent for the one pot conversion for the sterically and electronically hindered alcohol of carbohydrates into their corresponding chloride derivatives in excellent yield.

Benzotriazole is an anticorrosive agent, which is useful in aircraft deicing and antifreeze fluids. 
It is also employed in dishwasher detergents. 
Further, it is used as a restrainer in photographic emulsions and also useful as a reagent for the determination of silver in analytical chemistry. 
It also serves as a corrosion inhibitor in the atmosphere and underwater. 
Further, it is utilized in the synthesis of amines from glyoxal.
This Thermo Scientific brand product was originally part of the Alfa Aesar product portfolio. 
Some documentation and label information may refer to the legacy brand. 
The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific.

Benzotriazole is an anticorrosive agent, which is useful in aircraft deicing and antifreeze fluids. 
Benzotriazole is also employed in dishwasher detergents. 
Further, it is used as a restrainer in photographic emulsions and also useful as a reagent for the determination of silver in analytical chemistry. 
Benzotriazole also serves as a corrosion inhibitor in the atmosphere and underwater. 
Further, it is utilized in the synthesis of amines from glyoxal.

Benzotriazole is a synthetic auxiliary that offers many advantages. 
It is inexpensive, odorless, and stable. 
A benzotriazole group is easily introduced, activates molecules towards numerous transformations, and can be removed easily at the end of the reaction sequence. 
This Concept provides some recent examples of the synthetic application of benzotriazole methodology and is intended to draw attention to the versatile applications of benzotriazole in organic chemistry.

Benzotriazole is a corrosion inhibitor of high purity, most commonly used in yellow metal protection. 
Benzotriazole products are available as solids, salts and dissolved in glycols/alcohols. 
Solid benzotriazole products are off white to light yellow with very low odor. 
Benzotriazole is used as a vapor phase inhibitor and preferred for use in direct treatment of copper. 
Benzotriazole has a higher solubility in water than tolyltriazole, which aids in formulating.

Benzotriazole (BTA) is known for its great versatility. 
BTA is a corrosion inhibitor of high purity for copper, copper alloys, and yellow metal protection. 
Benzotriazole works by creating a complex between copper and benzotriazole which functions as a passivation layer to protect the metal from corrosion.  
BTA is also commonly used in water cooling systems. 
BTA can be used as a silver polishing agent in dishwasher detergent, automotive antifreeze, as a restrainer in photographic emulsions, and use as a lubricant additive. 

BTA can also be derived to create anti-fading agents for metals, antiseptic agents, UV-absorbers, pesticides, and photoconductors. 
BTA derivative are effective as drug precursors as well. 
BTA has more applications in brake fluids, cleaners, coatings and adhesives, flooring, fuels, inks, tires, and water treatment. 
Benzotriazole also possesses antihypertensive, antibacterial, analgesic, antifungal, antiviral, and anti-inflammatory properties.

Benzotriazole is a chemical substance that is used as a ligand to form complexes. 
Benzotriazole is used as a corrosion inhibitor for copper, high copper alloys, silver, cobalt, aluminum, and zinc. 
Benzotriazole is fairly well water-soluble, not readily degradable and has a limited sorption tendency.

First Aid Measures of Benzotriazole
EYES: 
First check the victim for contact lenses and remove if present. 
Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. 
Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. 
IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SKIN: 
IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. 
Gently wash all affected skin areas thoroughly with soap and water. 
If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.

INHALATION: 
IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. 
If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. 
Provide proper respiratory protection to rescuers entering an unknown atmosphere. 
Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.

INGESTION: 
DO NOT INDUCE VOMITING. 
If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. 
Be prepared to transport the victim to a hospital if advised by a physician. 
If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. 
DO NOT INDUCE VOMITING. 
IMMEDIATELY transport the victim to a hospital.

Substance identity

EC / List no.: 202-394-1
CAS no.: 95-14-7
Mol. formula: C6H5N3

Hazard classification & labelling of Benzotriazole
Warning! According to the classification provided by companies to ECHA in REACH registrations this substance is toxic to aquatic life with long lasting effects, causes serious eye irritation, is harmful if swallowed and causes skin irritation.

About Benzotriazole
Benzotriazole is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 000 to < 10 000 tonnes per annum.
Benzotriazole is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing and at industrial sites.

Consumer Uses of Benzotriazole
Benzotriazole is used in the following products: lubricants and greases, washing & cleaning products, heat transfer fluids, anti-freeze products and coating products.
Other release to the environment of this substance is likely to occur from: indoor use as processing aid, indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters), outdoor use in close systems with minimal release (e.g. hydraulic liquids in automotive suspension, lubricants in motor oil and break fluids) and outdoor use as processing aid.

Article service life of Benzotriazole
Other release to the environment of this substance is likely to occur from: indoor use in long-life materials with high release rate (e.g. release from fabrics, textiles during washing, removal of indoor paints) and outdoor use in long-life materials with high release rate (e.g. tyres, treated wooden products, treated textile and fabric, brake pads in trucks or cars, sanding of buildings (bridges, facades) or vehicles (ships)). 

Benzotriazole can be found in products with material based on: metal used for packaging (excluding food packaging) and plastic used for packaging (excluding food packaging). Benzotriazole is intended to be released from: packaging material for metal parts (releasing grease/corrosion inhibitors).

Widespread uses by professional workers of Benzotriazole
Benzotriazole is used in the following products: anti-freeze products, heat transfer fluids, lubricants and greases and washing & cleaning products.
Benzotriazole is used for the manufacture of: machinery and vehicles.
Other release to the environment of Benzotriazole is likely to occur from: indoor use as processing aid, indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters), outdoor use in close systems with minimal release (e.g. hydraulic liquids in automotive suspension, lubricants in motor oil and break fluids) and outdoor use as processing aid.

Formulation or re-packing of Benzotriazole
Benzotriazole is used in the following products: heat transfer fluids, lubricants and greases, anti-freeze products, washing & cleaning products, polymers and pH regulators and water treatment products.
Release to the environment of Benzotriazole can occur from industrial use: formulation of mixtures and formulation in materials.

Uses at industrial sites of Benzotriazole
Benzotriazole is used in the following products: lubricants and greases, heat transfer fluids, anti-freeze products and washing & cleaning products.
Benzotriazole is used for the manufacture of: machinery and vehicles, fabricated metal products and plastic products.
Release to the environment of Benzotriazole can occur from industrial use: in processing aids at industrial sites, of substances in closed systems with minimal release and in the production of articles.

Manufacture of Benzotriazole
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.

Synonyms:
1H-Benzotriazole
Benzotriazole
95-14-7
1H-Benzo[d][1,2,3]triazole
2H-Benzotriazole
1,2,3-BENZOTRIAZOLE
1H-1,2,3-Benzotriazole
Azimidobenzene
Aziminobenzene
Benztriazole
Benzisotriazole
Benzene azimide
2,3-Diazaindole
Cobratec #99
1,2-Aminoazophenylene
Cobratec 99
2H-benzo[d][1,2,3]triazole
1,2,3-Triaza-1H-indene
1,2,3-Triazaindene
273-02-9
1,2,-Aminozophenylene
NCI-C03521
NSC-3058
1,2,3-1h-benzotriazole
U-6233
UNII-86110UXM5Y
CHEBI:75331
1,2,3-Benztriazole
MFCD00005699
27556-51-0
DTXSID6020147
86110UXM5Y
1H-Benzotriazol
DSSTox_CID_147
DSSTox_RID_75400
DSSTox_GSID_20147
Benzotriazole (VAN)
benzotriazol
BtaH
CAS-95-14-7
CCRIS 78
Pseudoazimidobenzene
Cobratec 35G
HSDB 4143
1,2,3-Benzotriazole,1H-benzo[d][1,2,3]triazole
EINECS 202-394-1
azaindazole
BRN 0112133
aza-indazole
AI3-15984
3uzj
1 h-benzotriazole
1,3-Triazaindene
0CT
1,3-Benzotriazole
Cobratec No. 99
1,2-Aminozophenylene
1H-1,3-Benzotriazole
1,3-Triaza-1H-indene
1H-Benzotriazole (VAN8C
EC 202-394-1
WLN: T56 BMNNJ
SCHEMBL8956
1,2,3-Benzotriazole(BTA)
4-26-00-00093 (Beilstein Handbook Reference)
MLS002302971
CHEMBL84963
1H-benzo-[1,2,3]triazole
BDBM36293
NSC3058
Benzotriazole, analytical standard
HMS3091M10
ZINC332008
AMY37120
Benzotriazole, reagent grade, 97%
CS-D1407
STR01561
Tox21_201501
Tox21_302934
BDBM50234613
STL281967
Benzotriazole, ReagentPlus(R), 99%
1H-Benzotriazole, >=98.0% (N)
AKOS000119181
AKOS025396849
MCULE-2848618742
PS-3644
NCGC00091322-01
NCGC00091322-02
NCGC00091322-03
NCGC00256574-01
NCGC00259052-01
BP-21454
SMR001252218
DB-022595
B0094
BB 0243857
FT-0606217
FT-0698151
Benzotriazole, Vetec(TM) reagent grade, 98%
D77352
AB00374479-06
AC-907/34124039
Q220672
W-100172
Z57127352
F2190-0645
Benzotriazole
benzotriazole
1H-Benzotriazole
1,2,-Aminozophenylene
1,2,3 Benzotriazole
1,2,3-Benzotriazol
1,2,3-Benzotriazole
1,2,3-benzotriazole
1,2,3-Benzotriazole
1,2,3-Triazaindene
1,2,3-triazaindene
1H-1,2,3-benzotriazole
1H-Benzotriazol
1H-Benzotriazole
1H-benzotriazole
1H-benzotrizole
2H-Benzotriazole
2H-benzotriazole
Benzotriazol
benzotriazol
BENZOTRIAZOLE
Benzotriazole
benzotriazole
Benzotriazole
benzotriazole
Cobratec 1,2,3 BZ-G
BTA
CAC-BT99
115773-98-3
116421-31-9
1334724-96-7
152206-50-3
197463-08-4
25377-81-5
27556-51-0
28880-01-5
70644-74-5
83202-91-9
94160-69-7
95-14-7