73605-91-1

Basic information

• Product Name: 1H-Benzotriazole-5-carboxylic acid ethyl ester
• Synonyms: ETHYL 1H-BENZO[D][1,2,3]TRIAZOLE-5-CARBOXYLATE;Ethylbenzotriazole-5-carboxylate;1H-Benzotriazole-5-carboxylic acid ethyl ester;Ethyl 1H-1,2,3-benzotriazole-5-carboxylate;Ethyl benzotriazole-6-carboxylate
• CAS NO: 73605-91-1
• Molecular Formula: C₉H₉N₃O₂
• Molecular Weight: 191.19
• Mol File: 73605-91-1.mol
• Article Data: 10

Chemical Properties

• Melting Point: 108-109 °C
• Boiling Point: 356.8 °C at 760 mmHg
• Flash Point: 169.6 °C
• Appearance: /
• Density: 1.339
• Vapor Pressure: 2.85E-05mmHg at 25°C
• Refractive Index: 1.635
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 7.46±0.40(Predicted)
• CAS DataBase Reference: 1H-Benzotriazole-5-carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzotriazole-5-carboxylic acid ethyl ester(73605-91-1)
• EPA Substance Registry System: 1H-Benzotriazole-5-carboxylic acid ethyl ester(73605-91-1)

Safety Data

• Hazardous Substances Data: 73605-91-1(Hazardous Substances Data)

Usage

Stabilizer in plastic and polymer production

The compound helps to prevent the degradation of plastics and polymers during their production, ensuring a higher quality and longer-lasting final product.

Application in synthesis

Pharmaceutical, agrochemical, and dye production 1H-Benzotriazole-5-carboxylic acid ethyl ester is used as a key component in the synthesis of various pharmaceuticals, agrochemicals, and dyes, contributing to the development of new and improved products in these industries.

Versatility and importance in various industries

Due to its ability to prevent oxidation and degradation of materials, as well as its role in the production of other chemical compounds, 1H-Benzotriazole-5-carboxylic acid ethyl ester is considered a valuable and versatile chemical across numerous sectors.

InChI:InChI=1/C9H9N3O2/c1-2-14-9(13)6-3-4-7-8(5-6)11-12-10-7/h3-5H,2H2,1H3,(H,10,11,12)

Upstream product

• 23814-12-2 1h-benzotriazole-5-carboxylic acid 
• 64-17-5 ethanol 
• 36692-49-6 Methyl 3,4-diaminobenzoate 
• 3987-92-6 methyl 4-amino-3-nitrobenzoate 
• 1588-83-6 4-amino-3-nitrobenzoic acid 
• 113053-50-2 1H-Benzotriazole-5-carboxylic acid methyl ester 
• 23814-12-2 1H-benzo[d][1,2,3]triazole-5-carboxylic acid 
• 37466-90-3 ethyl 3,4-diaminobenzoate 

Downstream Products

• 23814-12-2 1h-benzotriazole-5-carboxylic acid 
• 64-17-5 ethanol 
• 106429-67-8 (1H-benzo[d][1,2,3]triazol-5-yl)methanol 
• 23814-12-2 1H-benzo[d][1,2,3]triazole-5-carboxylic acid 

Relevant articles and documents

Surface protection of copper by self-assembly of novel poly(5- methylenebenzotriazol-N-yl)

The novel polymer poly(5-methylenebenzotriazol-N-yl), denoted BTA-poly, was investigated for the protection of copper by electrochemical studies and weight loss measurements. The electrochemical measurements were compared to weight loss measurements and satisfactory results were obtained. Compared with benzotriazole, which is one of the best corrosion inhibitors for copper, BTA-poly achieves good protection under the same test conditions. Due to the rapid adsorption of BTA-poly onto copper, its corrosion-inhibition efficiency can be controlled by varying the concentration. The protecting effects of the polymers were studied in a sodium chloride solution using electrochemical measurements and an immersion test. The surface characteristics of the polymer-modified copper were analyzed via X-ray photoelectron spectroscopy (XPS), and scanning electron microscopy (SEM). These results show that BTA-poly can be easily adsorbed onto the copper surface via self-assembly to achieve excellent anticorrosion/antioxidation effects.

Investigation of the effect of different linker chemotypes on the inhibition of histone deacetylases (HDACs)

Histone Deacetylases (HDACs) are among the most attractive and interesting targets in anticancer drug discovery. The clinical relevance of HDAC inhibitors (HDACIs) is testified by four FDA-approved drugs for cancer treatment. However, one of the main drawbacks of these drugs resides in the lack of selectivity against the different HDAC isoforms, resulting in severe side effects. Thus, the identification of selective HDACIs represents an exciting challenge for medicinal chemists. HDACIs are composed of a cap group, a linker region, and a metal-binding group interacting with the catalytic zinc ion. While the cap group has been extensively investigated, less information is available about the effect of the linker on isoform selectivity. To this aim, in this work, we explored novel linker chemotypes to direct isoform selectivity. A small library of 25 hydroxamic acids with hitherto unexplored linker chemotypes was prepared. In vitro tests demonstrated that, depending on the linker type, some candidates selectively inhibit HDAC1 over HDAC6 isoform or vice versa. Docking calculations were performed to rationalize the effect of the novel linker chemotypes on biologic activity. Moreover, four compounds were able to increase the levels of acetylation of histone H3 or tubulin. These compounds were also assayed in breast cancer MCF7 cells to test their antiproliferative effect. Three compounds showed a significant reduction of cancer proliferation, representing valuable starting points for further optimization.

The discovery of new scaffold of plant activators: From salicylic acid to benzotriazole

Started from salicylic acid (SA) and related commercialized plant activators, based on molecular three-dimensional shape and pharmacophore similarity comparison (SHAFTS), a new lead compound benzotriazole was predicted and a series of benzotriazole derivatives were designed and synthesized. The bioassay showed that benzotriazole had high activity against a broad spectrum of diseases including fungi and oomycetes in vivo, but no activity in vitro. And the introduction of proper groups at the 1’-position and 5’-position was beneficial to the activity. So, they had the potential to be exploited as novel plant activators.