1224970-00-6

Basic information

• Product Name: 1-(o-ethynylphenyl)-3-phenylurea
• Synonyms: 1-(o-ethynylphenyl)-3-phenylurea
• CAS NO: 1224970-00-6
• Molecular Weight: 236.273
• Mol File: 1224970-00-6.mol

Chemical Properties

• CAS DataBase Reference: 1-(o-ethynylphenyl)-3-phenylurea(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(o-ethynylphenyl)-3-phenylurea(1224970-00-6)
• EPA Substance Registry System: 1-(o-ethynylphenyl)-3-phenylurea(1224970-00-6)

Safety Data

• Hazardous Substances Data: 1224970-00-6(Hazardous Substances Data)

Upstream product

• 52670-38-9 2-ethynylaniline 
• 103-71-9 phenyl isocyanate 

Downstream Products

• 16036-21-8 N-phenyl-1H-indole-1-carboxamide 
• 25809-80-7 3,4-dihydro-4-methylene-3-phenylquinazolin-2(1H)-one 
• 1610702-03-8 N-(4-methylene-1H-benzo[d][1,3]oxazin-2(4H)-ylidene)aniline 
• 1610702-09-4 1-(2-(1,1-diethoxyethyl)phenyl)-3-phenylurea 
• 1610702-14-1 4-methyl-3-phenyl-4-(2,2,2-trifluoroethoxy)-3,4-dihydroquinazolin-2(1H)-one 
• 1610702-27-6 1-(2-(1,1-bis(2,2,2-trifluoroethoxy)ethyl)phenyl)-3-phenylurea 
• 1563216-03-4 C₁₅H₁₁⁽²⁾HN₂O 
• 1563216-05-6 C₁₅H₁₁⁽²⁾HN₂O 

Relevant articles and documents

Competitive gold-activation modes in terminal alkynes: An experimental and mechanistic study

The competition between π- and dual σ,π-gold-activation modes is revealed in the gold(I)-catalyzed heterocyclization of 1-(o-ethynylaryl)urea. A noticeable effect of various ligands in gold complexes on the choice of these activation modes is described. The cationic [Au(IPr)]+ (IPr=2,6-bis(diisopropylphenyl)imidazol-2-ylidene) complex cleanly promotes the π activation of terminal alkynes, whereas [Au(PtBu3)]+ favors intermediate σ,π species. In this experimental and mechanistic study, which includes kinetic and cross-over experiments, several σ-gold, σ,π-gold, and other gold polynuclear reaction intermediates have been isolated and identified by NMR spectroscopy, X-ray diffraction, or MALDI spectrometry. The ligand control in the simultaneous or alternative π- and σ,π-activation modes is also supported by deuterium-labeling experiments. Copyright

NHC-stabilized gold(I) complexes: Suitable catalysts for 6-exo-dig heterocyclization of 1-(o-Ethynylaryl)ureas

Figure presented 3-substituted 1-(o-ethynylaryl)ureas 1 selectively undergo either 6-exo-dig or 5-endo-dig cyclization (to give 4-methylene-3,4-quinazolin- 2-ones 2 or indoles 3, respectively) depending on the choice of the metal, ligand, and reaction conditions. The best results (up to 96% yield) in the preparation of the hydroamination products 2 are achieved with the highly bulky NHC-stabilized cationic gold(I) complex [Au(IPr)]+. Conversely, ureas bearing an internal alkyne lead to the 5-endo-dig cyclization mode regardless of the gold(I) complex employed. Whereas the nature of the substituent at N-3 does not have any influence on the regiochemistry observed, it does, in some cases, affect the efficiency of these transformations.