106961-01-7

Basic information

• Product Name: N-(1,3-diphenyl-2-propynylidene)-N-phenylamine
• Synonyms: N-(1,3-diphenyl-2-propynylidene)-N-phenylamine
• CAS NO: 106961-01-7
• Molecular Formula: C₂₁H₁₅N
• Molecular Weight: 281.3505
• Mol File: 106961-01-7.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(1,3-diphenyl-2-propynylidene)-N-phenylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(1,3-diphenyl-2-propynylidene)-N-phenylamine(106961-01-7)
• EPA Substance Registry System: N-(1,3-diphenyl-2-propynylidene)-N-phenylamine(106961-01-7)

Safety Data

• Hazardous Substances Data: 106961-01-7(Hazardous Substances Data)

Upstream product

• 536-74-3 phenylacetylene 
• 201024-81-9 C,N-diphenylnitrone 
• 93-98-1 N-phenyl benzoyl amide 
• 1374324-65-8 C₂₂H₁₈N₂O 
• 4903-36-0 N-phenyl-benzimidoyl chloride 
• 33440-88-9 silver phenylacetylide 

Relevant articles and documents

Metal-free synthesis of quinolines by direct condensation of amides with alkynes: revelation of N-aryl nitrilium intermediates by 2D NMR techniques

Employing triflic anhydride/2-fluoropyridine as an activation system, the coupling reactions of secondary N-aryl amides with terminal alkynes yielded substituted quinolines in moderate to excellent yields. The reaction tolerated both electron-donating and electron-withdrawing groups at the benzamide moiety. Electron-rich aryl acetylenes served as excellent coupling partners, and aliphatic terminal alkynes such as cyclopropyl and conjugate vinyl acetylenes could also be used as reaction partners. By means of 2D NMR techniques (heteronuclear multiple bond correlation (HMBC), heteronuclear single quantum correlation (HSQC)), nitrilium ions were probed as reactive intermediates which are in contrast with that suggested by Movassaghi on the basis of in situ IR monitoring experiments. On the basis of these results, a plausible mechanism for the formation of quinolines was suggested.

Copper-Catalyzed Reaction of Terminal Alkynes with Nitrones. Selective Synthesis of 1-Aza-1-buten-3-yne and 2-Azetidinone Derivatives

Reaction of arylacetylenes with C,N-diarylnitrones using a catalyst system of CuI-dppe (dppe = 1,2-bis(diphenylphosphino)ethane) in the presence of potassium carbonate in DMF predominantly affords the corresponding 1,2,4-triaryl-1-aza-1-buten-3-ynes in good yields.In contrast, the catalytic reaction using CuI in the presence of an excess amount of pyridine as the ligand gives 1,3,4-triaryl-2-azetidinones as the major products.The reaction with aliphatic terminal alkynes in place of arylacetylenes produces the latter products irrespective of the catalyst system used.Asymmetric induction is also observed in the reaction of phenylacetylene with α,N-diphenylnitrone to give 1,2,4-triphenyl-2-azetidinone in the presence of chiral bisoxazoline-type ligands.

A convenient palladium-catalyzed synthesis of alkynyl substituted Schiff's bases by coupling of imidoyl chlorides with 1-alkynes

Alkyne substituted Schiff's bases 3 for example N-(1-phenyl-2-hexynylidene)aniline (3e), were conveniently synthesized from imidoyl chlorides 1 and 1-alkynes 2 in the presence of a palladium catalyst.