16584-04-6

Basic information

• Product Name: 2-Ethyl-2H-benzotriazole
• Synonyms: 2-Ethyl-2H-benzotriazole
• CAS NO: 16584-04-6
• Molecular Formula: C₈H₉N₃
• Molecular Weight: 147.18
• Mol File: 16584-04-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 65-70 °C(Press: 0.1 Torr)
• Appearance: /
• Density: 1.19±0.1 g/cm3(Predicted)
• PKA: 2.19±0.30(Predicted)
• CAS DataBase Reference: 2-Ethyl-2H-benzotriazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethyl-2H-benzotriazole(16584-04-6)
• EPA Substance Registry System: 2-Ethyl-2H-benzotriazole(16584-04-6)

Safety Data

• Hazardous Substances Data: 16584-04-6(Hazardous Substances Data)

Upstream product

• 830-67-1 ethyl 1H-benzo[d][1,2,3]triazole-1-carboxylate 
• 43183-36-4 1-(trimethylsilyl)-1H-benzotriazole 
• 68985-05-7 1,1′-carbonylbis-benzotriazole 
• 95-14-7 1,2,3-Benzotriazole 
• 74-96-4 ethyl bromide 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 141-97-9 ethyl acetoacetate 
• 51126-65-9 potassium salt of benzotriazole 
• 64-67-5 diethyl sulfate 

Downstream Products

• 300680-51-7 2-(Benzotriazol-2-yl)-2-butene 
• 95-14-7 1,2,3-Benzotriazole 

Relevant articles and documents

Sodium hydrogen exchanger inhibitory activity of benzotriazole derivatives

Series of benzotriazole derivatives were synthesized and evaluated for their Sodium hydrogen exchanger-1 inhibitory potential. All compounds inhibit Sodium hydrogen exchanger-1 in the in-vitro platelet swelling assay. This is perhaps the first report of NHE-1 inhibitory activity of benzotriazole. The 1-alkyl benzotriazole derivatives were found to be more active than the 2-alkyl isomers. The activity increases with increase in chain length of alkyl moiety. Potency increased from that of benzotriazole (IC50= 192.68 μM) to heptyl derivative (compound 13; IC50= 59.23 μM). Introduction of electronegative oxygen atom further increased potency as shown by the benzoyl (compound 16, IC50= 51.57 μM) and sulfonyl groups (compound 17, IC50= 50.89 μM; compound 18, IC50= 49.95 μM).

Organic reactions in ionic liquids: An efficient method for the N-alkylation of benzotriazole

The N-alkylation of benzotriazole with alkyl halides proceeds efficiently in the presence of potassium hydroxide in ionic liquid 1-butyl-3- methylimidazolium tetrafluoroborate ([Bmim][BF4]).

A Novel Selective Route to 1-Substituted Benzotriazoles via Lithiation of Simple 1-Alkylbenzotriazoles

1-Methylbenzotriazole (2a) is lithiated readily with butyllithium or LDA at the methyl group to 4 and the subsequent reaction with various electrophiles provides 1-substituted benzotriazoles 5.Other 1-(n-alkyl)benzotriazoles 2 also undergo lithiation with LDA, the carbanions can be trapped with alkyl halides giving benzotriazoles 6 bearing secondary alkyl groups on the N-1 atom.On standing in the absence of electrophiles, all the lithium derivatives decompose to afford complex mixtures. - Key Words: Benzotriazoles, 1-alkyl / Lithiation / Haloalkanes