16584-05-7

Basic information

• Product Name: 1-Ethyl-1H-benzotriazole
• Synonyms: 1-Ethyl-1H-benzotriazole
• CAS NO: 16584-05-7
• Molecular Formula: C₈H₉N₃
• Molecular Weight: 147.1772
• Mol File: 16584-05-7.mol

Chemical Properties

• Boiling Point: 279.7°Cat760mmHg
• Flash Point: 122.9°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 0.00672mmHg at 25°C
• Refractive Index: 1.634
• PKA: 1.47±0.30(Predicted)
• CAS DataBase Reference: 1-Ethyl-1H-benzotriazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Ethyl-1H-benzotriazole(16584-05-7)
• EPA Substance Registry System: 1-Ethyl-1H-benzotriazole(16584-05-7)

Safety Data

• Hazardous Substances Data: 16584-05-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 6022, 1989 DOI: 10.1021/jo00287a011

InChI:InChI=1/C8H9N3/c1-2-11-8-6-4-3-5-7(8)9-10-11/h3-6H,2H2,1H3

Upstream product

• 95-14-7 1,2,3-Benzotriazole 
• 74-96-4 ethyl bromide 
• 10467-10-4 ethylmagnesium iodide 
• 127236-78-6 N-(benzotriazol-1-ylmethyl)-N-methylpyrrolidinium iodide 
• 42003-33-8 C₃H₆Cl₃O₂P 
• 54187-96-1 1-(chloromethyl)-1H-benzotriazole 
• 1334478-49-7 3-benzyl-1-ethyl-1H-1,2,3-benzotriazol-3-ium bromide 
• 43183-36-4 1-(trimethylsilyl)-1H-benzotriazole 
• 68985-05-7 1,1′-carbonylbis-benzotriazole 
• 115054-74-5 ethyl α-(benzotriazol-1-yl)hexanoate 
• 28539-02-8 1-Hydroxymethyl-1H-benzotriazole 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 122-51-0 orthoformic acid triethyl ester 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 69218-29-7 1-isopropyl-1H-benzotriazole 

Relevant articles and documents

Ethylbenzotriazolium bromide ionic liquid: A new water soluble inhibitor for corrosion of mild steel in acid media

The inhibiting effect of 1-ethyl-3-ethylbenzotriazolium bromide ionic liquid, [C2Et]Br, on the corrosion behaviour of mild steel in 5 wt. % HCl was investigated by using various techniques such as weight loss, potentiodynamic polarization and e

Degradation of Organic Cations under Alkaline Conditions

Understanding the degradation mechanisms of organic cations under basic conditions is extremely important for the development of durable alkaline energy conversion devices. Cations are key functional groups in alkaline anion exchange membranes (AAEMs), and AAEMs are critical components to conduct hydroxide anions in alkaline fuel cells. Previously, we have established a standard protocol to evaluate cation alkaline stability within KOH/CD3OH solution at 80 °C. Herein, we are using the protocol to compare 26 model compounds, including benzylammonium, tetraalkylammonium, spirocyclicammonium, imidazolium, benzimidazolium, triazolium, pyridinium, guanidinium, and phosphonium cations. The goal is not only to evaluate their degradation rate, but also to identify their degradation pathways and lead to the advancement of cations with improved alkaline stabilities.

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).

Convenient and stereoselective synthesis of symmetrical (E)-stilbenes via homocoupling of 1,3-dibenzylbenzotriazolium bromides

Using NaH as the base and DMSO as the solvent, a series of symmetric (E)-stilbenes were prepared in good yields via the -homocoupling of 1,3-dibenzylbenzotriazolium bromides at room temperature. Georg Thieme Verlag Stuttgart · New York.

Green and efficient protocol for N-alkylation of benzotriazole using basic ionic liquid [Bmim]OH as catalyst under solvent-free conditions

N-Alkylation of benzotriazole bearing an acidic hydrogen atom attached to nitrogen with alkyl halides is accomplished in basic ionic liquid [Bmim]OH (1-butyl-3-methylimidazolium hydroxide) under solvent-free conditions. The procedure is convenient and efficient and generally affords the N-alkylated product. Taylor & Francis Group, LLC.

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]).

Condensation of benzotriazole with O-alkyl P-(dichloromethyl) chlorophosphonate: Some unusual observations

The condensation of benzotriazole with O-alkyl P-(dichloromethyl) chlorophosphonate give corresponding 1-alkylbenzotriazole rather than desired N-(benzotriazol-1-yl) P-(dichloromethyl) O-alkyl phosphonate.

Reactions of Benzotriazoles with Diethyl Ethoxymethylenemalonate; Ethylation and Michael Addition. Comparison with Other Esters and N-Heterocycles

Benzotriazole and its 5-methyl- and 5-nitro derivatives react with diethyl ethoxymethylenemalonate by ethylation at each of the ring N-atoms and through Michael addition, to give the isomeric esters ethyl (E/Z) 3-[5(6)-R-benzotriazol-1-yl]propenoates. Benzotriazole and its 5-nitro derivative react similarly with ethyl acetoacetate but N-ethyl derivatives are obtained in lower yields. Other 1,2,3-triazoles derivatives and indole were ineffective in this reaction while benzimidazole produced similar results but accompanied with a small amount of a benzimidazoline addition product, whose structure has been detenruned by crystallographic analysis.

Lewis Acid-Catalyzed Additions of (Benzotriazol-1-yl)diethoxymethane to Enol Ethers and Enamides. New Syntheses of β-Alkoxyalkanal and β-Aminoalkanal Acetals

Addition of (benzotriazol-1-yl)diethoxymethane 11 to various acyclic and cyclic enol ethers and enamides produces the corresponding adducts, which were reacted with either NaAlH4 or Grignard reagents to afford acyclic acetal-ethers (18a-f), cyclic α-(substituted)-β-acetals (19a-c), amino-acetals (24a,b), and 1,3-amino-ethers (25), all known but previously difficult-to-access classes of compounds.

A simple, versatile synthetic route to N-1-aryl-, -heteroaryl-, -acylmethyl-, -carboxymethyl- and -alkyl-benzotriazoles via regiospecific or highly regioselective substitutions of benzotriazole

In the absence of any added base in refluxing benzene or toluene, benzotriazole replaces the halogen atom of an α-halogenated ketone or a carboxylic ester to give the corresponding N-1-substituted benzotriazole as the only isomer. 2-Bromopyridine and 1-chloro-2,4-dinitrobenzene reacted similarly with benzotriazole to afford the corresponding N-1-substituted benzotriazole derivatives in quantitative yields. Alkyl halides reacted regioselectively to afford the N-1-alkylbenzotriazoles in ratios of more than 10 to 1 over the N-2 isomers. An α-(benzotriazol-1-yl)carboxylic ester was hydrolyzed into the corresponding carboxylic acid, which upon heating underwent smooth decarboxylation into the corresponding 1-alkylbenzotriazole.