104919-73-5

Basic information

• Product Name: Carbamic acid, [2-(phenylethynyl)phenyl]-, ethyl ester
• CAS NO: 104919-73-5
• Molecular Formula: C17H15NO2
• Molecular Weight: 265.312
• Mol File: 104919-73-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [2-(phenylethynyl)phenyl]-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [2-(phenylethynyl)phenyl]-, ethyl ester(104919-73-5)
• EPA Substance Registry System: Carbamic acid, [2-(phenylethynyl)phenyl]-, ethyl ester(104919-73-5)

Safety Data

• Hazardous Substances Data: 104919-73-5(Hazardous Substances Data)

Upstream product

• 104919-70-2 ethyl (2-bromophenyl)carbamate 
• 536-74-3 phenylacetylene 
• 64-17-5 ethanol 
• 80221-08-5 2-(2-phenylethynyl)benzamide 
• 98952-64-8 N-ethoxycarbonyl-2-iodoaniline 

Downstream Products

• 857809-85-9 ethyl 2,3-diphenyl-1H-indole-1-carboxylate 
• 948-65-2 2-phenyl-indole 

Relevant articles and documents

N-carboxylated-2-substituted indoles and 2,3-disubstituted-2,3-dihydro-4- quinolones from 2- alkynylbenzamides

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InBr3-promoted divergent approach to polysubstituted indoles and quinolines from 2-ethynylanilines: Switch from an intramolecular cyclization to an intermolecular dimerization by a type of terminal substituent group

(Chemical Equation Presented) Use of a 2-ethynylaniline having an alkyl or aryl group on the terminal alkyne selectively produced a variety of polyfunctionalized indole derivatives in moderate to excellent yields via indium-catalyzed intramolecular cyclization of the corresponding alkynylaniline. In contrast, employment of a substrate with a trimethylsilyl group or with no substituent group on the terminal triple bond, exclusively afforded polysubstituted quinoline derivatives in good yields via indium-promoted intermolecular dimerization of the ethynylaniline. This indium catalytic system successfully accommodated the intramolecular cyclization of other arylalkyne skeletons involving a carboxylic acid and an amide group.

Convenient synthesis of 2-substituted indoles from 2-ethynylanilines with tetrabutylammonium fluoride

The cyclization reaction of various 2-ethynylanilines, which were easily synthesized from 2-haloanilines by the palladium-catalyzed reaction with terminal alkynes, with tetrabutylammonium fluoride (TBAF) to yield 2-substituted indoles proceeded at refluxing or room temperature in THF in excellent yields without affecting the bromo, chloro, cyano, ethoxycarbonyl, and ethynyl groups.