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2H-ベンゾトリアゾール

1H-Benzotriazole

HCID 7220
ノート反応
基本情報名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
273-02-9
標準SMILES
c1ccc2n[nH]nc2c1
InChIKey
QRUDEWIWKLJBPS-UHFFFAOYSA-N
分子式
C6H5N3
平均分子量
119.12 g/mol
単同位体質量
119.04834717

名称と識別子

優先名称
1H-Benzotriazole
IUPAC
2H-benzotriazole
現地名
2H-ベンゾトリアゾール
英語名
Pseudoazimidobenzene
分子式
C6H5N3
分子量
119.12

名称と別名

1H-BenzotriazoleBenzotriazole95-14-71,2,3-BENZOTRIAZOLEAzimidobenzene1H-1,2,3-BenzotriazoleBenzisotriazoleAziminobenzeneBenztriazoleBenzene azimide2,3-Diazaindole1,2-Aminoazophenylene
名称をさらに表示
2H-ベンゾトリアゾール2H-1,2,3-ベンゾトリアゾール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

データベース識別子

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

物性

構造計算による物性

XLogP
1
極性表面積
41.6 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
0
重原子数
9
形式電荷
0
複雑度
92

実験および物理化学的性質

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

1.36 g/cu cm at 20 °C

1.36 g/cm³

Color/Form · 2 件

Needles from chloroform or benzene

White to light tan, crystalline powder

Solubility · 6 件

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

Flash Point · 2 件

170 °C (338 °F) - closed cup

190-195 °C o.c.

Boiling Point · 4 件

399 °F at 15 mmHg (NTP, 1992)

BP: 204 °C at 15 mm Hg

Decomposes below the boiling point at 260 °C

at 2 kPa: 204 °C

Decomposition · 3 件

Hazardous decomposition products formed under fire conditions - Carbon oxides, nitrogen oxides (NOx).

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

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.

危険有害性情報

Regulatory Information · 6 件

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 件

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

化学と産業

薬理情報

Metabolism/Metabolites · 2 件

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.

用途と製造

Uses · 6 件

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.

関連反応

8 件
反応記録を作成
HRID 334660 の反応式
HRID 334660生成物としてuspto-grants-2014_11
HRID 422343 の反応式
HRID 422343生成物としてuspto-grants-2012_01
HRID 422375 の反応式
HRID 422375反応物としてuspto-grants-2012_01
HRID 422382 の反応式
HRID 422382生成物としてuspto-grants-2012_01
HRID 422388 の反応式
HRID 422388生成物としてuspto-grants-2012_01
HRID 422403 の反応式
HRID 422403生成物としてuspto-grants-2012_01
HRID 1154505 の反応式
HRID 1154505反応物としてuspto-grants-1984_12
HRID 1189187 の反応式
HRID 1189187生成物としてuspto-grants-2014_03

化合物ノート

読み込み中…

このページの内容基本情報名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

When heated to decomposition it emits toxic fumes of /nitrogen oxides/.

260 °C

Melting Point · 3 件

208 to 212 °F (NTP, 1992)

100 °C

98.5 °C

Vapor Density4.1 (Air = 1)
Vapor Pressure · 2 件

Vapor pressure: <0.01 kPa at 25 °C

Vapor pressure, Pa at 20 °C: 5

物理化学的性質

沸点
276.1 · 276.1±23.0 °C(Predicted)
比重(密度)
1.348 · 1.348±0.06 g/cm3(Predicted)
酸解離定数(Pka)
8.38 · 8.38±0.10(Predicted)
TSCA Requirements · 1 件

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.

Reactivity AlertsExplosive
Reactivity Profile · 1 件

The triazoles are a group of highly explosive materials that are sensitive to heat, friction, and impact. Sensitivity varies with the type substitution to the triazole ring. Metal chelated and halogen substitution of the triazol ring make for a particularly heat sensitive material. Azido and nitro derivatives have been employed as high explosives. No matter the derivative these materials should be treated as explosives.

Chemical DangersDecomposes on heating. This produces toxic fumes including aniline and nitrobenzene. The solution in water is a weak acid. May explode on vacuum distillation.
Physical DangersDust explosion possible if in powder or granular form, mixed with air.
Air and Water ReactionsDust may form an explosive mixture in air. Slightly soluble in water.
Hazard Classes and Categories · 3 件

Acute Tox. 4 (96.7%);Eye Irrit. 2 (87.8%);Acute Tox. 4 (37.7%);Aquatic Chronic 2 (25%);Aquatic Chronic 3 (35.5%)

Acute toxicity (Oral) - Category 4;Acute toxicity (Inhalation: Dusts and mists) - Category 4;Serious eye damage/eye irritation - Category 2;Specific target organ toxicity - Single exposure - Category 2 (respiratory system), Category 3 (narcotic effects)

Aquatic Chronic 2

安全と保護具

Fire Fighting · 2 件

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 件

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 件

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 件

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.
Cleanup Methods · 1 件

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.;STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

Disposal Methods · 2 件

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material; Contaminated packaging: Dispose of as unused product.

Spillage Disposal · 1 件

Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance.

Preventive Measures · 5 件

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Provide appropriate exhaust ventilation at places where dust is formed.

Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

Stable under recommended storage conditions.

For more Preventive Measures (Complete) data for 1,2,3-Benzotriazole (6 total), please visit the HSDB record page.

Eye PreventionWear safety spectacles.

毒性情報

Interactions · 2 件

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 件

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 件

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 件

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.

Ecotoxicity Excerpts · 5 件

/AQUATIC SPECIES/ Benzotriazole (BT) and its associated derivatives are used ubiquitously in industrial processes, and can be detected in indoor temperature coolants and in chemicals designed to inhibit corrosion. This chemical has been widely detected in aquatic environments and shows some degree of environmental persistence. Evidence has shown that BT exposure can negatively affect endocrine systems and can result in neurotoxicity in fish. However, no study has examined whether this chemical exhibits hepatotoxicity in fish, and if so, what are the underlying mechanism associated with the damage. To address this knowledge gap, we measured the liver proteome of adult male Chinese rare minnow (Gobiocypris rarus) exposed to either 0.05, 0.5, or 5 mg/L BT for 28 days. Overall, 17 proteins were induced and 9 were reduced in abundance following BT treatment (ratio > 1.5, p < 0.05). Pathway analysis revealed that cellular processes affected by BT included xenobiotic clearance, oxidative stress response, apoptosis, and translation. Moreover, transcripts related to these toxic pathways were also significantly affected by BT. In addition, rare minnows exposed to BT showed signs of hypertrophy of hepatocytes, nuclei pyknosis, and higher levels of cellular vacuolization compared to the controls, thus these early proteomic responses in the liver may be related to pathology (i.e. adverse outcome pathway). Our data demonstrate that BT dysregulates molecular responses in the liver and tissue pathology indicative of damage. This study provides new insight into BT hepatotoxicity in Chinese rare minnow.

/AQUATIC SPECIES/ Benzotriazoles (BZTs) are ubiquitous aquatic contaminants used in a wide range of industrial and domestic applications from aircraft deicers to dishwasher tablets. Acute toxicity has been reported in aquatic organisms for some of the BZTs but their mode of action remains unknown. The objectives of this study were to evaluate the transcriptomic response of D. magna exposed to sublethal doses of 1H-benzotriazole (BTR), 5-methyl-1H-benzotriazole (5MeBTR) and 5-chloro-1H-benzotriazole (5ClBTR) using RNA-sequencing and quantitative real-time PCR. Cellular and life-history endpoints (survival, number of neonates, growth) were also investigated. Significant effects on the molting frequency were observed after 21-day exposure to 5MeBTR and 5ClBTR. No effects on molting frequency were observed for BTR but RNA-seq results indicated that this BZT induced the up-regulation of genes coding for cuticular proteins, which could have compensated the molting disruption. Molting in cladocerans is actively controlled by ecdysteroid hormones. Complementary short-term temporal analysis (4- and 8-day exposure) of the transcription of genes related to molting and hormone-mediated processes indicated that the three compounds had specific modes of action. BTR induced the transcription of genes involved in 20-hydroxyecdysone synthesis, which suggests pro-ecdysteroid properties. 5ClBTR exposure induced protein activity and transcriptional levels of chitinase enzymes, associated with an impact on ecdysteroid signaling pathways, which could explain the decrease in molt frequency. Finally, 5MeBTR seemed to increase molt frequency through epigenetic processes. Overall, results suggested that molting effects observed at the physiological level could be linked to endocrine regulation impacts of BZTs at the molecular level.

Signs and SymptomsRedness. Pain.
Ongoing Test Status · 2 件

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of November 16, 2017: http://actor.epa.gov/dashboard/]

The following link will take the user to the National Toxicology Program (NTP) Test Status of Agents Search page, which tabulates the results and current status of tests such as "Short-Term Toxicity Studies", "Long-term Carcinogenicity Studies", "Developmental Studies", "Genetic Toxicology Studies", etc., performed with this chemical. Testing status for 1,2,3-benzotriazole is available.[Available from, as of November 3, 2017: https://ntpsearch.niehs.nih.gov/?e=True&ContentType=Testing+Status]

Effluent Concentrations · 1 件

Monitoring at a municipal wastewater treatment plant in Berlin, Germany detected influent and effluent 1,2,3-benzotriazole concentrations of 11.9 and 9.6 ug/L respectively(1). Sewage sludge collected from wastewater treatment plants along the Songhua River, China contained 1,2,3-benzotriazole concentrations of 17.2-198 ng/g dry wt(2). In 2010, effluents from 90 European wastewater treatment plants (WWTPs) were analyzed for 156 polar organic chemical contaminants, and 1,2,3-benzotriazole was detected at a frequency of 97% with average, median and maximum concentrations of 6.3, 2.7 and 221 ug/L respectively(3). The minimum, maximum and median concentrations of 1,2,3-benzotriazole detected in the effluent of a WWTP in Switerland (12 samples) were 2.7, 6.0 and 4.3 mg/L respectively(4). Wastewater sampled from a WWTP in Brandenburg, Germany contained a 1,2,3-benzotriazole concentrations of 34 ug/L(5).

ICSC Environmental DataThe substance is harmful to aquatic organisms.
Soil Adsorption/Mobility · 1 件

1,2,3-Benzotriazole Freundlich adsorption isotherms measured from topsoil and subsoil collected from the Moreppen, Oslo Norway airport were 4.26 and 0.2-0.4 respectively(1); based on respective soil organic content of 0.82 and 0.10%(1), Koc values of 200 to 520 can be calculated(SRC). Using five Eurosoil types (pH range of 5.2 to 8.6, organic content range of 0.33 to 1.85%), 1,2,3-benzotriazole had measured Kd values ranging from about 0.1 to 0.8(2) which correspond to a Koc range of about 10 to 90(SRC). A measured Koc value 49 has also been reported(3). According to a classification scheme(4), these Koc values suggest that 1,2,3-benzotriazole is expected to have very high to moderate mobility in soil. Sorption in soil is influenced by surface complexation of the neutral species, pH, ion exchange(2) and metal content in the soil(1). The pKa of 1,2,3-benzotriazole is 8.37(5), 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(6). Results of sorption tests at pH 5.2 to 8.6 indicated that 1,2,3-benzotriazole existed primarily as the neutral species(2). Sorption studies in a column using aquifer sediments determined a Koc value of 81(7).

法規制情報

Regulatory Information · 6 件

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 件

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.

安全データ

注意喚起語
警告
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H302

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 件

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 件

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

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

Household ProductsInformation on 40 consumer products that contain Benzotriazole in the following categories is provided:;• Auto Products;• Commercial / Institutional;• Inside the Home
Use Classification · 2 件

Cosmetics -> Antimicrobial

Corrosion inhibitors

General Manufacturing Information · 2 件

Wholesale and Retail Trade;Computer and Electronic Product Manufacturing;Petroleum Lubricating Oil and Grease Manufacturing;Soap, Cleaning Compound, and Toilet Preparation Manufacturing;Services;All Other Basic Organic Chemical Manufacturing;Other (requires additional information);Not Known or Reasonably Ascertainable;All Other Chemical Product and Preparation Manufacturing;Fabricated Metal Product Manufacturing;Non-metallic Mineral Product Manufacturing (includes clay, glass, cement, concrete, lime, gypsum, and other non-metallic mineral product manufacturing);Paint and Coating Manufacturing

1H-Benzotriazole: ACTIVE

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/AQUATIC SPECIES/ 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.

/AQUATIC SPECIES/ Benzotriazole (BT) is a high-production volume chemical which has been ubiquitously detected in aquatic environments. Although adverse effects from acute and chronic exposure to BT have been reported, the neurotoxic effect of BT and the mechanisms of toxicity are not well documented. In this study, adult female Chinese rare minnow (Gobiocypris rarus) were exposed to 0.05, 0.5, and 5 mg/L BT for 28 days. The brain proteome showed that BT exposure mainly involved in metabolic process, signal transduction, stress response, cytoskeleton, and transport. Pathway analysis revealed that cellular processes affected by BT included cellular respiration, G-protein signal cascades, Ca2+-dependent signaling, cell cycle and apoptosis. Moreover, data on relative mRNA levels demonstrated that genes related to these toxic pathways were also significantly affected by BT. Furthermore, proteins affected by BT such as CKBB /creatine kinase, brain b/, GS /glutamine synthetase/, HPCA /hippocalcin/, VDAC1 /voltage-dependent anion channel 1/, and FLOT1A /flotillin 1a/ are associated with neurological disorders. Therefore, our finding suggested that BT induced molecular responses in the brain and could provide new insight into BT neurotoxicity in Chinese rare minnow.

For more Ecotoxicity Excerpts (Complete) data for 1,2,3-Benzotriazole (14 total), please visit the HSDB record page.