118521-81-6

Basic information

• Product Name: 2-(2H-benzo[d][1,2,3]triazol-2-yl)acetonitrile
• Synonyms: 2-(2H-benzo[d][1,2,3]triazol-2-yl)acetonitrile
• CAS NO: 118521-81-6
• Molecular Formula: C₈H₆N₄
• Molecular Weight: 158.16004
• Mol File: 118521-81-6.mol

Chemical Properties

• Melting Point: 77-78 °C
• Boiling Point: 349.3±44.0 °C(Predicted)
• Appearance: /
• Density: 1.30±0.1 g/cm3(Predicted)
• PKA: 0.37±0.30(Predicted)
• CAS DataBase Reference: 2-(2H-benzo[d][1,2,3]triazol-2-yl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2H-benzo[d][1,2,3]triazol-2-yl)acetonitrile(118521-81-6)
• EPA Substance Registry System: 2-(2H-benzo[d][1,2,3]triazol-2-yl)acetonitrile(118521-81-6)

Safety Data

• Hazardous Substances Data: 118521-81-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(2H-benzo[d][1,2,3]triazol-2-yl)acetonitrile is utilized as a building block for the synthesis of a variety of bioactive molecules and pharmaceutical drugs. Its unique structure allows for the creation of new compounds with potential therapeutic effects.
Used in Organic Synthesis:
In the realm of organic synthesis, 2-(2H-benzo[d][1,2,3]triazol-2-yl)acetonitrile serves as a versatile intermediate. It is instrumental in the preparation of a diverse array of compounds, contributing to the development of new chemical entities with specific applications.
Used in Material Science:
2-(2H-benzo[d][1,2,3]triazol-2-yl)acetonitrile also finds potential applications in the field of material science. Its properties may be harnessed to develop new materials with unique characteristics for various uses.
Used as a Fluorescent Probe in Biological Research:
Furthermore, this chemical compound has potential as a fluorescent probe in biological research. Its fluorescent properties can be employed to track and visualize biological processes, offering insights into cellular mechanisms and interactions.

Upstream product

• 95-14-7 1,2,3-Benzotriazole 
• 107-14-2 chloroacetonitrile 
• 590-17-0 cyanomethyl bromide 

Downstream Products

• 288072-07-1 2-benzotriazol-2-yl-3-p-tolyl-acrylonitrile 
• 288072-09-3 (E)-2-Benzotriazol-2-yl-3-(4-chloro-phenyl)-acrylonitrile 
• 288072-13-9 (E)-2-Benzotriazol-2-yl-3-(4-nitro-phenyl)-acrylonitrile 
• 55-22-1 pyridine-4-carboxylic acid 
• 95-14-7 1,2,3-Benzotriazole 
• 840501-01-1 N-{(S)-3-[4-((E)-2-Benzotriazol-2-yl-2-cyano-vinyl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide 

Relevant articles and documents

Synthesis and characterization of benzotriazolyl acrylonitrile analogs-based donor-acceptor molecules: Optical properties, in vitro cytotoxicity, and cellular imaging

A series of eight new (E)-benzotriazolyl acrylonitrile derivatives were synthesized under reflux conditions via Knoevenagel condensation between acetonitrile analogs and a short series of aromatic aldehydes. X-ray diffraction analysis for one of the compounds was performed to determine the (E)-geometry of its double bond. The photoluminescent properties of all compounds in solution were also evaluated. These compounds exhibit strong blue, green and yellow emission under ultraviolet light excitation with fluorescence quantum yield in the 0.08–0.58% range. To determine the suitability of these compounds for use in cell-based analysis, cytotoxicity assays were performed on a representative molecule using a common mammalian cell line (HEK 293T cells) at different concentrations. The results showed limited toxicity (72 ± 16% viability) at the highest concentration tested (50 μM). Finally, confocal microscopy demonstrated that our compound was internalized into cells and localized to endosomes and/or lysosomes in a similar fashion to Dextran–Cascade Blue (DCB).

Synthesis and anticancer activity of benzotriazole derivatives

A series of benzotriazole (BTA) derivatives were synthesized as tyrosine protein kinase inhibitors using fragment-based design strategy. All desired compounds were synthesized with the reaction of benzotriazole, chloroacetonitrile and aromatic aldehyde using Ultrasonic-Microwave method and characterized by IR, 1H and 13C-NMR, mass spectrometry (MS) and elemental analysis. The anticancer activity of these compounds was evaluated by CCK-8 method against carcinoma VX2, lung cancer A549, stomach cancer cell lines MKN45 and MGC in vitro. The results showed that all compounds showed good antiproliferative activity. In particular, compound 2.1 showed the most prominent inhibition of VX2 cell lines with IC50 of 3.80 ± 0.75 μM. Compound 2.2 exhibited highly potent anticancer activity of stomach MGC cell lines with IC50 of 3.72 ± 0.11 μM. A549 and MKN45 cell lines were sensitive to compound 2.5 with IC50 of 5.47 ± 1.11 and 3.04 ± 0.02 μM, respectively.

Synthesis, crystal structure and photo- and electro-luminescence of the coumarin derivatives with benzotriazole moiety

Two new coumarin derivatives containing an electron-transporting moiety (benzotriazole), 7-N,N-diethylamino-3-(benzotriazol-1-yl)coumarin (DABTC-1) and 7-N,N-diethylamino-3-(benzotriazol-2-yl)coumarin (DABTC-2), were synthesized and characterized by element analysis, 1H NMR, FT-IR and UV-vis absorption spectra. Their structures were determined by X-ray crystallography single crystal analysis. The photoluminescent behaviors of the compounds in both solution and solid states were observed, they exhibit strong blue and blue-green emissions under ultraviolet light excitation, respectively. The energy levels of the HOMO and LUMO of the compounds have been calculated with density functional theory (DFT) and time-dependent density functional theory (TD-DFT) at B3LYP/6-31G(d) level. The electroluminescent devices with the compounds as the emitters were fabricated.

Effects of positional and geometrical isomerism on the biological activity of some novel oxazolidinones

Some novel oxazolidinone derivatives have been synthesized and tested for antibacterial activity. Compound 13 was found to be active against Gram-positive pathogens whereas compound 14 was less active. Either less active or inactive molecules were obtained, when benzotriazole was replaced with benzimidazole, benzthiazole, or benzoxazole. However, thioacetamide analogue of 13 produced a potent molecule similar to linezolid in vitro. Some novel oxazolidinone derivatives with benzotriazole as pendant have been synthesized and tested for antibacterial activity. Linearly attached benzotriazole derivative showed more potency compared to angular one in vitro. Out of E/Z-isomers of angularly attached derivatives E-isomer was found to be more potent than Z-isomer. Either less active or inactive molecules were obtained, when benzotriazole was replaced with benzimidazole, benzthiazole, or benzoxazole. Finally, thioacetamide analogue of linear compound gave a lead having activity similar to linezolid in vitro.

Synthesis and antiproliferative activity of 3-aryl-2-[1H(2H)-benzotriazol- 1(2)-yl]acrylonitriles variously substituted: Part 4

A new series of variously substituted 3-aryl-2-[1H(2H)-benzotriazol-1(2)- yl]acrylonitriles was synthesized and tested for antiproliferative and antitubercular activity as part of our continuing research program in the antimicrobial and antitumor fields. The most cytotoxic derivatives (5a,g,i,j,l and 7b) (CC50 3.0 μM against MT-4 cells) were evaluated against a panel of human cell lines derived from hematological and solid tumors, using 6-mercaptopurine (6-MP) and etoposide as reference drugs. In particular, E-2-(5,6-dimethyl-1H-benzotriazol-1-yl)-3-(3-nitrophenyl)acrylonitrile (5g) resulted more potent than 6-MP on all cell lines, even if 2-14-fold less potent than etoposide. In the antitubercular screening, the derivatives 5i,j and 7e showed moderate activity against some resistant strains of Mycobacterium tested.

Synthesis and antitubercular activity of 3-aryl substituted-2-(1H(2H) benzotriazol-1(2)-yl)acrylonitriles

A series of 223-aryl substituted-2-(1H(2H)-benzotriazol-1(2)- yl)acrylonitriles was synthesized for a preliminary in vitro evaluation of antitubercular activity according to an international program with the Tuberculosis Antimicrobial Acquisition and Coordinating Facility (TAACF). This work reports the synthetic approach and analytical and spectroscopic characterization (UV, IR, 1H- and 13C-NMR) of all compounds synthesized. Several compounds showed an interesting activity in the preliminary screening with a percent growth inhibition of the virulent Mycobacterium tuberculosis between 40 and 99% at the concentration of 12.5 μg/mL. The most effective derivatives E-5a and E-5e were also tested against M. avium in vitro. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

Synthesis and antiparasitic activities of amidinic azolated derivatives

A set of heterocyclic N-acetamidinium hydrochlorides were prepared from the corresponding N-acetonitriles. The antiparasitic screening showed that, while all amidines are practically inactive, some nitriles present leishmanicide properties.