209912-23-2

Usage

Type of compound

Benzotriazole derivative

Common use

Building block in organic synthesis

Photophysical properties

Interesting properties that make it useful in various applications

Electrochemical properties

Interesting properties that make it useful in various applications

Applications

a. Organic light-emitting diodes (OLEDs)
b. Organic photovoltaics (OPVs)
c. Sensor technology

Potential

Candidate for the development of new materials in the field of organic electronics and optoelectronics

Biological activities

Studied for potential biological activities

Drug discovery and development

Under investigation for its role in drug discovery and development

Upstream product

• 79069-32-2 phenyl(phenylethynyl)iodonium tosylate 
• 51126-65-9 potassium salt of benzotriazole 
• 95-14-7 1,2,3-Benzotriazole 
• 314765-25-8 (E)-2-(1H-1,2,3-benzotriazol-1-yl)-1-phenylethenyl trifluoromethanesulfonate 
• 361379-14-8 (Z)-2-(1H-1,2,3-benzotriazol-1-yl)-1-phenylethenyl trifluoromethanesulfonate 
• 127876-36-2 2-(benzotriazol-1-yl)acetophenone 
• 98-88-4 benzoyl chloride 
• 122296-00-8 1-<(trimethylsilyl)methyl>benzotriazole 

Downstream Products

• 101-41-7 benzeneacetic acid methyl ester 
• 4805-17-8 2-(phenylethynyl)thiophene 
• 77234-10-7 2-(2phenylethynyl)benzo[b]furan 
• 14374-45-9 1-heptynylbenzene 
• 4289-20-7 1-phenyl-4-penten-1-yne 

Relevant academic research and scientific papers

A novel access to disubstituted acetylenes

Reactions of organometallic reagents with 1-(substituted ethynyl)-1H-1,2,3-benzotriazoles 5 derived from a variety of benzotriazolylmethyl ketones 3 afforded disubstituted acetylenes in synthetically useful yields.

One-carbon homologation of carboxylic acids via BtCH2TMS: A safe alternative to the Arndt-Eistert reaction

Carboxylic acids are converted into the corresponding homologated acids or esters, using easily available 1-(trimethylsilylmethyl)benzotriazole (1) as a one-carbon synthon. The effectiveness of the reaction has been investigated on six aryl and seven alkyl carboxylic acids.

Preparation of resin-bound alkynyl iodonium salts and their application in organic synthesis as alkynyl transfer reagents

We have synthesized polymer-supported alkynylphenyl iodonium salts. They served as effective alkynyl transfer reagents for the preparation of acetylenic sulfones; the by-product, polymer supported (4-iodostyrene), could be reactivated for reuse numerous t

BtCH2TMS-assisted Homologation of Carboxylic Acids: A Safe Alternative to the Arndt-Eistert Reaction

formula presented One-carbon homologation of carboxylic acids is achieved by (i) treatment of an acyl chloride with 1-[(trimethylsilyl)methyl]-1H-1,2,3,-benzotriazole (BtCH2TMS) (1) to afford N-(acylmethyl)benzotriazoles 3a-f, followed by (ii) conversion of 3a-f with triflic anhydride into RC(OTf)=CHBt 4a-f, and (iii) the subsequent reaction of 4a-c with NaOCH3 followed by 1N HCl to afford esters RCH2CO2R′ 7a-c in overall yields of 50-70%. For the aliphatic compounds 5d-f, treatment of 5d-f with p-toluenesulfonic acid followed by TBAF/THF afforded acids RCH2COOH 7d-f.

A convenient synthesis of new 1-alkynyl-1H-benzotriazoles by reaction of alkynyl(phenyl)iodonium salts with benzotriazole ion

The reaction of arylethynyl(phenyl)iodonium tosylates with benzotriazole ion gave new 1-alkynyl-1H-benzotriazoles in good yields. This result indicates that alkynyliodonium salts can be used for direct alkynylation of benzotriazole. However, the similar reactions of (tert- butylethynyl)(phenyl)iodonium and 1-octynyl(phenyl)iodonium tosylates do not afford the 1-alkynyl-1H-benzotriazoles but alkenylbenzotriazoles via the reaction of alkylidenecarbenes.

Alkynylbenzotriazoles by direct alkynylation of benzotriazole using alkynyliodonium salts

Alkynyl(phenyl)iodonium salts react with benzotriazole ion prepared from benzotriazole and potassium t-butoxide to give 1-alkynylbenzotriazoles in good yields, indicating that the alkynyliodonium salts can be used for direct alkynylation of benzotriazole.