209912-23-2

Basic information

• Product Name: 1-(Phenylethynyl)-1H-benzo[d][1,2,3]triazole
• Synonyms: 1-(Phenylethynyl)-1H-benzo[d][1,2,3]triazole
• CAS NO: 209912-23-2
• Molecular Formula: C14H9N3
• Molecular Weight: 219.246
• Mol File: 209912-23-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1-(Phenylethynyl)-1H-benzo[d][1,2,3]triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(Phenylethynyl)-1H-benzo[d][1,2,3]triazole(209912-23-2)
• EPA Substance Registry System: 1-(Phenylethynyl)-1H-benzo[d][1,2,3]triazole(209912-23-2)

Safety Data

• Hazardous Substances Data: 209912-23-2(Hazardous Substances Data)

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

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

Downstream Products

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

Relevant articles and documents

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.

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.