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1H-Benzotriazole

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1H-Benzotriazole Basic information
1H-Benzotriazole Chemical Properties
  • Melting point:97-99 °C(lit.)
  • Boiling point:204 °C (15 mmHg)
  • Density 1,36 g/cm3
  • vapor density 4.1 (vs air)
  • vapor pressure 0.04 mm Hg ( 20 °C)
  • refractive index 1.5589 (estimate)
  • Flash point:170 °C
  • storage temp. Refrigerator
  • solubility 19g/l
  • form Powder, Granules, Crystals, Needles or Flakes
  • pka1.6(at 20℃)
  • color White to yellow-beige
  • OdorSlight characteristic odor
  • PH6.0-7.0 (100g/l, H2O, 20℃)suspension
  • explosive limit2%
  • Water Solubility 25 g/l in water (20 ºC)
  • Merck 14,1108
  • BRN 112133
  • Stability:Stable, but may be light sensitive. Incompatible with strong oxidizing agents, heavy metals.
  • InChIKeyQRUDEWIWKLJBPS-UHFFFAOYSA-N
  • CAS DataBase Reference95-14-7(CAS DataBase Reference)
  • NIST Chemistry Reference1H-Benzotriazole(95-14-7)
  • EPA Substance Registry System1,2,3-Benzotriazole (95-14-7)
Safety Information
MSDS
1H-Benzotriazole Usage And Synthesis
  • Chemical Propertiesyellow to beige solid
  • UsesBenzotriazole (BT) is an anticorrosive agent well known for its use in aircraft deicing and antifreeze fluids but also used in dishwasher detergents. in vivo.
  • Usesanticorrosive 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. (HSDB 1998).
    Benzotriazole(BTA), ethylenediamine tetraaceticacid(EDTA), and potassium iodide(KI) were used for preparing the polishing slurries.
  • DefinitionChEBI: The simplest member of the class of benzotriazoles that consists of a benzene nucleus fused to a 1H-1,2,3-triazole ring.
  • Synthesis Reference(s)The Journal of Organic Chemistry, 27, p. 185, 1962 DOI: 10.1021/jo01048a046
  • General DescriptionWhite to light tan crystals or white powder. No odor.
  • Air & Water ReactionsDust may form an explosive mixture in air. Slightly soluble in water.
  • Reactivity ProfileThe 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.
  • HazardHighly toxic by ingestion. May explode under vacuum distillation.
  • Health HazardACUTE/CHRONIC HAZARDS: When heated to decomposition 1H-Benzotriazole emits toxic fumes. 1H-Benzotriazole can react violently during vacuum distillation.
  • Fire HazardFlash point data are not available for 1H-Benzotriazole. 1H-Benzotriazole is probably combustible.
  • Safety ProfilePoison by intravenous route.Moderately toxic by ingestion and intraperitoneal routes.Questionable carcinogen with experimental tumorigenicdata. Mutation data reported. May detonate at 220°C or during vacuum distillation. When heated to decompositionit
  • Potential ExposureBecause benzotriazoles are used in large quantities as a corrosion inhibitor, it is mainly through this type of use that benzotriazoles become an environmental contaminant. As a corrosion inhibitor and fire retardant, they are used in antifreeze in concentrations of 0.01-2.0% and in airplane deicing/antiicing fluids in unknown concentrations, up to 10% (Cancilla et al.,1997). Used antifreeze may leak or be poured down drains and thence enters the environment. Also, an estimated 80% of aircraft deicing/anti-icing fluids are deposited on the ground due to spray drift, jet blast, and wind shear during taxiing and takeoff, according to a recent study (Hartwell et al., 1995).
  • CarcinogenicityChronic (2-year) feeding studies were conducted. Rats were given 0, 6700, or 12,000 ppm in feed for 78 weeks and held for an additional 26 weeks. Mice were given 0, 11,700, or 23,500 ppm in feed in 104 weeks. The authors concluded that under the conditions shown in this study, there were no convincing evidence that 1-H-benzotriazole was carcinogenic in rats or mice.
  • Purification Methods1,2,3-Benzotriazole crystallises from toluene, CHCl3, Me2NCHO or a saturated aqueous solution, and is dried at room temperature or in a vacuum oven at 65o. Losses are less if the material is distilled in a vacuum. CAUTION: may EXPLODE during distillation; necessary precautions must be taken. [Damschroder & Peterson Org Synth Coll Vol III 106 1955, Beilstein 26 III/IV 93.]
  • Toxicity evaluationAccording to a 1977 EPA report, benzotriazole is considered to be of very low toxicity and a low health hazard to humans. In the same EPA report, two benzotriazole derivatives were reported to be mutagenic in bacterial systems. A year later, NIH published a report that there was no convincing evidence that the compound is carcinogenic (NIH, 1978). It is, however, more recently well established that 1-amino benzotriazole, with an amino group attached to one of the ring nitrogens, is a potent mechanism-based inhibitor of cytochrome P-450s via a benzyne intermediate (Ortiz de Montellano and Mathews, 1981), indicating that benzotriazoles as a class may interact with the P-450s. The P450s are important both for detoxifying a broad range of xenobiotics and for activating many compounds to carcinogens in mammalian systems.
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