142321-23-1

Basic information

• Product Name: 1-(2-PROPYNYL)-1H-BENZOTRIAZOLE
• Synonyms: 1-(2-PROPYNYL)-1H-BENZOTRIAZOLE;1-PROPARGYL-1H-BENZOTRIAZOLE;1-prop-2-ynylbenzotriazole
• CAS NO: 142321-23-1
• Molecular Formula: C₉H₇N₃
• Molecular Weight: 157.17
• Mol File: 142321-23-1.mol
• Article Data: 16

Chemical Properties

• Melting Point: 52-56 °C(lit.)
• Boiling Point: 302.2°C at 760 mmHg
• Flash Point: 136.6°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 0.0018mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: 1-(2-PROPYNYL)-1H-BENZOTRIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-PROPYNYL)-1H-BENZOTRIAZOLE(142321-23-1)
• EPA Substance Registry System: 1-(2-PROPYNYL)-1H-BENZOTRIAZOLE(142321-23-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 142321-23-1(Hazardous Substances Data)

Usage

Uses

Reactant for:Preparation of clarithromycin analogs via click chemistry as antibacterial agentsSonogashira couplingBronsted superacid-catalyzed reactionsHydroboration and hydrostannylation reactions

InChI:InChI=1/C9H7N3/c1-2-7-12-9-6-4-3-5-8(9)10-11-12/h1,3-6H,7H2

Upstream product

• 95-14-7 1,2,3-Benzotriazole 
• 106-96-7 propargyl bromide 
• 107-19-7 propargyl alcohol 

Relevant articles and documents

The preparation of 1,5-dioxygenated-pent-2-ynes

1,5-Dioxygenated-pent-2-ynes were prepared via the reductive lithiations of 4-alkoxybut-2-ynylbenzotriazoles and subsequent condensations with ketones and aldehydes.

Synthesis and antimicrobial evaluation of 1,4-disubstituted 1,2,3-triazoles containing benzofused N-heteroaromatic moieties

Synthesis of a small library of 1,4-disubstituted 1,2,3-triazoles containing benzofused N-heteroaromatic moieties was carried out through click reaction of various benzofused N-heteroaromatic alkynes with aromatic azides. All the synthesized compounds were characterized by spectroscopic techniques like IR, 1H NMR, 13C NMR, mass spectrometry and evaluated in vitro for antimicrobial activity against two Gram-positive bacteria (Bacillus subtilis, Staphylococcus aureus), one Gram-negative bacteria (Escherichia coli) and two fungi (Candida albicans, Aspergillus Niger). Most of the synthesized 1,4-disubstituted 1,2,3-triazoles were found to possess significant antibacterial and antifungal activity against tested microbial species. Moreover, docking simulation of the compound 1-[(1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)methyl]-1H-benzo[d]imidazole was also carried out against E. coli topoisomerase II DNA gyrase B enzyme to study the binding modes and mechanism of action.

Design, click conventional and microwave syntheses, DNA binding, docking and anticancer studies of benzotriazole-1,2,3-triazole molecular hybrids with different pharmacophores

Despite the availability of some drugs, there is an urgent need for effective anti-cancer medication. It is due to various side effects and non-functionality of the present drugs; especially at the late stage of cancer. Therefore, three series (4a-e, 6a-e and 8a-j; 21 compounds) of benzotriazole-1,2,3-triazole hybrids (carrying different pharmacophores) have been designed and synthesized (by both conventional and microwave syntheses) through the Cu(I)-catalyzed click 1,3-dipolar cycloaddition reaction of the propargylated benzotriazole with the appropriate aliphatic, aromatic and phenyl/benzyl acetamide azides. The syntheses times were from 6 to 12 h and 4 to 8 min in conventional and microwave syntheses. The yields were 80 to 86percent and 89 to 95percent in conventional and microwave syntheses; confirming microwave synthesis as an economic and eco-friendly method. These compounds were characterized by proper spectroscopic methods. The anticancer activities with A549 and H1299 lung cancer cell lines were in the range of 70.0 to 90.0percent for 4a-e series, 78.0 to 90.0percent for 6a-e series and 81.0 to 90.0percent for 8a-j series. The reported compounds showed good DNA binding constants in the range of 1.3 × 103 to 11.90 × 105 M?1. The docking results suggested strong DNA bindings of the reported compounds in the minor grooves of DNA; through hydrogen bonding and hydrophobic interactions. The quite good anticancer activities and high DNA binding constants have indicated that the reported molecules may be future anticancer agents.