199276-69-2

Basic information

• Product Name: (4-azidobut-1-yn-1-yl)benzene
• Synonyms: (4-azidobut-1-yn-1-yl)benzene
• CAS NO: 199276-69-2
• Molecular Weight: 171.202
• Mol File: 199276-69-2.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (4-azidobut-1-yn-1-yl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (4-azidobut-1-yn-1-yl)benzene(199276-69-2)
• EPA Substance Registry System: (4-azidobut-1-yn-1-yl)benzene(199276-69-2)

Safety Data

• Hazardous Substances Data: 199276-69-2(Hazardous Substances Data)

Upstream product

• 10229-11-5 4-phenyl-but-3-yn-1-ol 
• 85375-43-5 4-methyl-N-(4-phenylbut-3-yn-1-yl)benzenesulfonamide 
• 53422-48-3 2-chloroethyl azide 
• 1004-22-4 (phenylethynyl)sodium 

Downstream Products

• 3042-22-6 2-phenyl-1H-pyrrole 
• 97505-87-8 2-phenylpyrroline 
• 135469-70-4 4-phenyl-3-butyn-1-amine 
• 182324-83-0 4-methyl-N-(4-phenylbut-3-yn-1-yl)benzenesulfonamide 
• 700-91-4 2-phenyl-1-pyrroline 

Relevant articles and documents

Atom-Economical Cross-Coupling of Internal and Terminal Alkynes to Access 1,3-Enynes

Selective carbon-carbon (C-C) bond formation in chemical synthesis generally requires prefunctionalized building blocks. However, the requisite prefunctionalization steps undermine the overall efficiency of synthetic sequences that rely on such reactions, which is particularly problematic in large-scale applications, such as in the commercial production of pharmaceuticals. Herein, we describe a selective and catalytic method for synthesizing 1,3-enynes without prefunctionalized building blocks. In this transformation several classes of unactivated internal acceptor alkynes can be coupled with terminal donor alkynes to deliver 1,3-enynes in a highly regio- and stereoselective manner. The scope of compatible acceptor alkynes includes propargyl alcohols, (homo)propargyl amine derivatives, and (homo)propargyl carboxamides. This method is facilitated by a tailored P,N-ligand that enables regioselective addition and suppresses secondary E/Z-isomerization of the product. The reaction is scalable and can operate effectively with as low as 0.5 mol % catalyst loading. The products are versatile intermediates that can participate in various downstream transformations. We also present preliminary mechanistic experiments that are consistent with a redox-neutral Pd(II) catalytic cycle.

The acid-mediated intramolecular 1,3-dipolar cycloaddition of derived 2-nitro-1,1-ethenediamines for the synthesis of novel fused bicyclic isoxazoles

The discovery of a novel synthesis of new fused bicyclic isoxazoles, for example, N-methyl-3-phenyl-5,6-dihydro-4H-isoxazolo[3,4-c]azepin-8-amine (2a), N-methyl-3-phenyl-4,5-dihydroisoxazolo[3,4-c]pyridin-7-amine (2b) and N-methyl-3-phenyl-4H-pyrrolo[3,4-

Et2Zn-catalyzed intramolecular hydroamination of alkynyl sulfonamides and the related tandem cyclization/addition reaction

(Chemical Equation Presented) Intramolecular hydroamination of alkynyl amides was effected by a catalytic amount of Et2Zn (20 mol %) to form indole derivatives, and a tandem cyclization/nucleophilic addition procedure involving reaction of the indole zinc salt intermediate with acid chlorides or halides was developed to provide an efficient approach to C3-substituted indole derivatives when an excess of Et2Zn (120 mol %) was used.