1H-Benzotriazole

HCID 7220

Basic information

CAS
273-02-9
Standard SMILES
c1ccc2n[nH]nc2c1
InChIKey
QRUDEWIWKLJBPS-UHFFFAOYSA-N
Molecular formula
C6H5N3
Average molar mass
119.12 g/mol
Monoisotopic mass
119.04834717

Names & identifiers

Preferred name
1H-Benzotriazole
IUPAC
2H-benzotriazole
English name
Pseudoazimidobenzene
Molecular formula
C6H5N3
Molecular weight
119.12

Names & synonyms

1H-BenzotriazoleBenzotriazole95-14-71,2,3-BENZOTRIAZOLEAzimidobenzene1H-1,2,3-BenzotriazoleBenzisotriazoleAziminobenzeneBenztriazoleBenzene azimide2,3-Diazaindole1,2-Aminoazophenylene
Show more names
2H-benzo[d][1,2,3]triazole2H-BenzotriazolePseudoazimidobenzene
1,2,3-1h-benzotriazole1,2,3-TriazaindeneCobratec 991,2,-Aminozophenylene1,2,3-Triaza-1H-indeneCobratec 35GNSC-3058DTXSID6020147

Database identifiers

CAS
273-02-9、95-14-7
PubChem CID
7220
DTXSID
DTXSID6020147
ChEMBL
CHEMBL84963
ChEBI
CHEBI:75331
UNII
86110UXM5Y
EC Number
202-394-1
Nikkaji
J259.309B、J4.709K

Properties

Computed structural properties

XLogP
1
Topological polar surface area
41.6 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
9

Experimental & physicochemical properties

pHThe solution in water is a weak acid
LogPlog Kow= 1.44
OdorNo odor
Density · 2 items

1.36 g/cu cm at 20 °C

1.36 g/cm³

Color/Form · 2 items

Needles from chloroform or benzene

White to light tan, crystalline powder

Solubility · 6 items

1 to 5 mg/mL at 74.7 °F (NTP, 1992)

In water, 1.98X10+4 mg/L at 25 °C

In water, 1-5 g/L at 23.7 °C

Slightly soluble in water

Soluble in alcohol, benzene, toluene, chloroform and N,N-dimethylformamide

Soluble in ethanol, benzene, chloroform, toluene, DMF

Physicochemical properties

Boiling point
276.1 · 276.1±23.0 °C(Predicted)
Density
1.348 · 1.348±0.06 g/cm3(Predicted)
pka
8.38 · 8.38±0.10(Predicted)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P273, P391, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 2% (37 of 1870) of reports.

Hazard information

Regulatory Information · 6 items

Chemical: 1H-Benzotriazole

Chemical: 2H-Benzotriazole

1H-Benzotriazole is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1H-Benzotriazole are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Status: Active Update: 20-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14234;Status: Active Update: 20-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/27455

Benzotriazole: Does not have an individual approval but may be used under an appropriate group standard

Fire Hazards · 2 items

Flash point data are not available for this compound. It is probably combustible. (NTP, 1992)

Combustible. Finely dispersed particles form explosive mixtures in air.

Health HazardsACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. This compound can react violently during vacuum distillation. (NTP, 1992)
Hazards SummaryBenzotriazole is a potential skin sensitizer used in the aircraft industry as a corrosion inhibitor. [Kanerva, p. 1259] An eye irritant; May cause skin sensitization; [ICSC]
Reactive GroupAzo, Diazo, Azido, Hydrazine, and Azide Compounds;Hydrocarbons, Aromatic
TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2,3-Benzotriazole is included on this list. Effective date: 4/13/89; Sunset date: 12/19/95.

Safety & protection

Fire Fighting · 2 items

Fires involving this compound can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray.

First Aid Measures · 4 items

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

First Aid · 1 item

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. (NTP, 1992)

Safe StorageWell closed.
Fire Fighting Procedures · 2 items

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place.

Toxicology

Interactions · 2 items

Benzotriazole (BTR), an emerging class of environmental pollutant, is widely used in industrial applications and household dishwashing agents. Despite the reported toxicity of BTR to aquatic organisms, little is known about its effects on terrestrial invertebrates. Copper (Cu) accumulates in agricultural soils receiving urban waste products, fertilizers, fungicides, and urban sewage. In this study, two different types of bioassays (acute toxicity test and behavioral toxicity test) were performed to evaluate the toxicity of Cu and BTR, both singly and together, on the earthworm (Eisenia fetida) in artificial soil. The results of avoidance behavior tests showed that the EC50 (48 hr) values for Cu and BTR were 1.47 and 0.46 mmol/kg, respectively. The results of the acute toxicity tests showed that the LC50 (7 d) and LC50 (14 d) of Cu in earthworms were 9.19 and 5.28 mmol/kg, respectively, and the LC50 (7 d) and LC50 (14 d) of BTR were 2.43 and 1.76 mmol/kg, respectively. Toxicity analysis demonstrated that the binary BTR and Cu mixture had predominantly antagonistic effects on the avoidance behavior and survival of earthworms. The Cu2+ activities and mortality of earthworms decreased significantly with increasing concentrations of BTR, while the solid-liquid distribution coefficient of Cu increased. These results indicated that the presence of BTR can reduce the toxicity as well as the bioavailability of Cu in soil with both BTR and Cu.

As an emerging contaminant, 1-H-benzotriazole (1H-BTR) has been detected in the engineered and natural aquatic environments, which usually coexists with heavy metals and causes combined pollution. In the present study, wild-type and transgenic zebrafish Danio rerio were used to explore the acute toxicity as well as the single and joint hepatotoxicity of cadmium (Cd) and 1H-BTR. Although the acute toxicity of 1H-BTR to zebrafish was low, increased expression of liver-specific fatty acid binding protein was observed in transgenic zebrafish when the embryos were exposed to 5.0 uM of 1H-BTR for 30 days. Besides, co-exposure to 1H-BTR not only reduced the acute toxic effects induced by Cd, but also alleviated the Cd-induced liver atrophy in transgenic fish. Correspondingly, effects of combined exposure to 1H-BTR on the Cd-induced expressions of several signal pathway-related genes and superoxide dismutase and glutathione-s-transferase proteins were studied. Based on the determination of Cd bioaccumulation in fish and the complexing stability constant (beta) of Cd-BTR complex in solution, the detoxification mechanism of co-existing 1H-BTR on Cd to the zebrafish was discussed.

Ecotoxicity Values · 5 items

EC50; Species: Eisenia fetida (Earthworm) body weight 300-400 mg; Conditions: Artificial soil (70% industrial sand, 20% kaolin clay, and 10% finely ground peat), pH 6.0 +/- 0.5; Concentration: 0.46 mmol/kg for 48 hr (95% confidence interval: 0.41-0.51 mmol/kg); Effect: avoidance behavior. /99% purity/

LC50; Species: Eisenia fetida (Earthworm) body weight 300-400 mg; Conditions: Artificial soil (70% industrial sand, 20% kaolin clay, and 10% finely ground peat), pH 6.0 +/- 0.5; Concentration: 2.43 mmol/kg for 7 days (95% confidence interval: 2.21-2.71 mmol/kg) /99% purity/

LC50; Species: Eisenia fetida (Earthworm) body weight 300-400 mg; Conditions: Artificial soil (70% industrial sand, 20% kaolin clay, and 10% finely ground peat), pH 6.0 +/- 0.5; Concentration: 1.76 mmol/kg for 14 days (95% confidence interval: 1.69-1.82 mmol/kg) /99% purity/

LC50; Species: Dugesia japonica (Flatworm) body length 0.8 cm; Conditions: freshwater, static, 25 °C; Concentration: 171100 ug/L for 24 hr (95% confidence interval: 161700-181100 ug/L) /100% purity/

For more Ecotoxicity Values (Complete) data for 1,2,3-Benzotriazole (7 total), please visit the HSDB record page.

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an experimentally derived Koc range of 10 to 500(2,3) indicates that 1,2,3-benzotriazole is expected to have very high to moderate mobility in soil(SRC). Sorption in soil is influenced by surface complexation of the neutral species, pH, ion exchange(3) and metal content in the soil(2). The pKa of 1,2,3-benzotriazole is 8.37(4), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Results of sorption tests at pH 5.2 to 8.6 indicated that 1,2,3-benzotriazole existed primarily as the neutral species(3). Volatilization of 1,2,3-benzotriazole from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.5X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(6). A 2% of theoretical BOD using activated sludge in the Japanese MITI test(7) indicates that 1,2,3-benzotriazole is not readily biodegradable(SRC). The results of other screening tests and soil degradation studies indicated that 1,2,3-benzotriazole is stable with regard to biodegradation in soils under environmental conditions with a half-life >180 days(8). A compilation of biodegradation rate constants in soil and groundwater for 1,2,3-benzotriazole has a range of 0.001 to 0.016/day(9) which has a corresponding half-life range of 43 to 693 days(SRC). Anaerobic soil column studies(10) suggest biodegradation may occur faster under anaerobic conditions(SRC).

AQUATIC FATE: Based on a classification scheme(1), an experimentally derived Koc range of 10 to 500(2,3) indicates that 1,2,3-benzotriazole may have some adsorption to suspended solids and sediment(SRC). Sorption is influenced by surface complexation of the neutral species, pH, ion exchange(3) and metal content in the sediment(2). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 1.5X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), a BCF range of 1.1 to 15 measured in carp (Cyprinus carpio), suggests bioconcentration in aquatic organisms is low(SRC). A 2% of theoretical BOD using activated sludge in the Japanese MITI test(7) indicates that 1,2,3-benzotriazole is not readily biodegradable(SRC). The results of other screening tests indicate that 1,2,3-benzotriazole is stable with regard to biodegradation based on little or no observed degradation over periods of 4 weeks or longer(8). 1,2,3-Benzotriazole is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). 1,2,3-Benzotriazole is slowly photodecomposed by irradiation at 300 nm in aqueous solutions(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,2,3-benzotriazole, which has an estimated vapor pressure of 2.5X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 1,2,3-benzotriazole is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 16 days(SRC), calculated from its rate constant of 1.0X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase 1,2,3-benzotriazole may be removed from the air by wet or dry deposition(SRC). 1,2,3-Benzotriazole absorbs at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
Toxicity Summary · 1 item

IDENTIFICATION AND USE: 1,2,3-Benzotriazole (BT) is a white to light tan, crystalline powder. It is used as photographic restrainer and a chemical intermediate. It is also a corrosion inhibitor in industrial water treatment, and in the treatment of bronze disease in metal fine art conservation. HUMAN STUDIES: A report showed that two metal workers developed contact dermatitis from exposure to lubricating oil that contained BT. ANIMAL STUDIES: In a test for primary skin irritation and sensitization on guinea pigs, BT was at most mildly irritating in concentrations up to 50% in ethanol and was not a sensitizer. The dry powder is severely irritating to rabbit eyes (0.1 mL unwashed) but prompt water washing reduces irritation considerably. BT was positive in the Salmonella typhimurium and Escherichia coli mutagenicity assays. ECOTOXICITY STUDIES: This chemical has been widely detected in aquatic environments and shows some degree of environmental persistence. BT exposure can negatively affect endocrine systems and can result in neurotoxicity in fish. BT demonstrated hepatotoxicity and neurotoxicity in Chinese rare minnow. In female marine medaka, exposure to 0.01 mg/L BT caused notable changes in expression levels of vitellogenin, CYP1A1 and CYP19a. In vitro assays conducted using a recombinant yeast (anti-) estrogen assay indicated that BT possessed clear antiestrogenic properties. BT metabolism by plants could mask the presence of BT contamination in the environment. Furthermore, BT-derived metabolites are structurally related to plant auxin hormones.

Regulatory information

Regulatory Information · 6 items

Chemical: 1H-Benzotriazole

Chemical: 2H-Benzotriazole

1H-Benzotriazole is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1H-Benzotriazole are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Status: Active Update: 20-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14234;Status: Active Update: 20-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/27455

Benzotriazole: Does not have an individual approval but may be used under an appropriate group standard

TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2,3-Benzotriazole is included on this list. Effective date: 4/13/89; Sunset date: 12/19/95.

Safety data

Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H302-H315-H319-H335
Precautionary statements
P261-P305+P351+P338

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

Benzotriazoles (BTs) are xenobiotic contaminants widely distributed in aquatic environments and of emerging concern due to their polarity, recalcitrance, and common use. During some water reclamation activities, such as stormwater bioretention or crop irrigation with recycled water, BTs come in contact with vegetation, presenting a potential exposure route to consumers. We discovered that BT in hydroponic systems was rapidly (approximately 1-log per day) assimilated by Arabidopsis plants and metabolized to novel BT metabolites structurally resembling tryptophan and auxin plant hormones; <1% remained as parent compound. Using LC-QTOF-MS untargeted metabolomics, we identified two major types of BT transformation products: glycosylation and incorporation into the tryptophan biosynthetic pathway. BT amino acid metabolites are structurally analogous to tryptophan and the storage forms of auxin plant hormones. Critical intermediates were synthesized (authenticated by (1)H/(13)C NMR) for product verification. In a multiple-exposure temporal mass balance, three major metabolites accounted for >60% of BT. Glycosylated BT was excreted by the plants into the hydroponic medium, a phenomenon not observed previously. The observed amino acid metabolites are likely formed when tryptophan biosynthetic enzymes substitute synthetic BT for native indolic molecules, generating potential phytohormone mimics. These results suggest that BT metabolism by plants could mask the presence of BT contamination in the environment. Furthermore, BT-derived metabolites are structurally related to plant auxin hormones and should be evaluated for undesirable biological effects.

1-H-Benzotriazole was metabolized by rat liver microsomes in vitro to 4-hydroxybenzotriazole and 5-hydroxybenzotriazole.

Uses & manufacturing

Uses · 6 items

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; [Kanerva, p. 717]

Metal Machining [Category: Heat or Machine];Photographic Processing [Category: Other]

Photographic restrainer, chemical intermediate.

Gravimetrically, silver is determined by precipitation with ... 1,2,3-benzotriazole.

Aqueous benzotriazole (1% v/v) with 5% ethanol (v/v) is used to remove considerable amount of chloride-containing corrosion products on bronzes.

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

U.S. Imports(1979) 1.32X10+7 GRAMS (PRINCPL CUSTMS DISTS)
U.S. Production · 4 items

2023: 2,500,000 - <4,000,000 lb;2022: 2,500,000 - <4,000,000 lb;2021: 2,500,000 - <4,000,000 lb;2020: 1,000,000 - <2,500,000 lb

(1977) PROBABLY GREATER THAN 6.81X10+6 GRAMS

(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 1H-Benzotriazole:;Table: National Aggregate Production Volume (pounds) [Table#4829]

Consumer UsesOther;Anti-adhesive/cohesive;Anti-freeze agent;Preservative;Corrosion inhibitor;Not Known or Reasonably Ascertainable
Industry UsesAnti-scaling agent;Intermediate;Not Known or Reasonably Ascertainable;Corrosion inhibitor;Plating agent;Anti-freeze agent;Anti-adhesive/cohesive;Lubricating agent;Other
Methods of Manufacturing · 2 items

... obtained by the reaction of o-phenylenediamine with nitrous acid in dilute sulfuric acid.

Prepared by the action of nitrous acid on o-phenylenediamine.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山东隆汇化工有限公司531-88613858 15562516958 · [email protected]

Additional notes

DefinitionChEBI: 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.

Related reactions

8 records

Compound notes

Loading…