33675-45-5

Basic information

• Product Name: 1-(bromoethynyl)-3-methoxylbenzene
• Synonyms: 1-(bromoethynyl)-3-methoxylbenzene
• CAS NO: 33675-45-5
• Molecular Weight: 211.058
• Mol File: 33675-45-5.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 1-(bromoethynyl)-3-methoxylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(bromoethynyl)-3-methoxylbenzene(33675-45-5)
• EPA Substance Registry System: 1-(bromoethynyl)-3-methoxylbenzene(33675-45-5)

Safety Data

• Hazardous Substances Data: 33675-45-5(Hazardous Substances Data)

Upstream product

• 591-31-1 3-methoxy-benzaldehyde 
• 253684-23-0 1,1-dibromo-2-(3-methoxyphenyl)ethene 
• 766-85-8 3-methoxy-1-iodobenzene 
• 768-70-7 1-ethynyl-3-methoxybenzene 

Downstream Products

• 934001-90-8 CH₃OCC₅H₄C₆H₁₁O₂C₃NOBr 
• 219801-01-1 5-(3-methoxyphenyl)-2-phenyl-1H-imidazole 
• 1332532-78-1 (Z)-4-bromo-1-(3-methoxyphenyl)-3-propylhept-3-en-1-yne 
• 1338248-69-3 3-(3-methoxyphenyl)imidazo[1,2-a]pyridine 
• 934002-00-3 CH₃OC₆H₄C₄H₃O₂NBr 
• 1432655-43-0 (E)-methyl 1-(1-bromo-2-(3-methoxyphenyl)vinyl)-1H-indole-3-carboxylate 
• 1432655-42-9 (E)-methyl 1-(1-iodo-2-(3-methoxyphenyl)vinyl)-1H-indole-3-carboxylate 
• 1432655-47-4 methyl 1-((3-methoxyphenyl)ethynyl)-1H-indole-3-carboxylate 

Relevant articles and documents

Visible-Light-Promoted Formation of C—C and C—P Bonds Derived from Evolution of Bromoalkynes under Additive-Free Conditions: Synthesis of 1,1-Dibromo-1-en-3-ynes and Alkynylphosphine Oxides

The controllable achievement of C—C and C—P bond formations is developed via visible-light-promoted bromoalkyne dimerization or its further transformation with secondary phosphine oxides. The 1,1-dibromo-1-en-3-ynes are formed when bromoalkyne is exposed to visible-light. While alkynylphosphine oxides are generated when bromoalkynes are mixed with secondary phosphine oxides.

Regio- and Stereoselective N-addition to an Open Bromo Vinyl Cation

A protocol for the synthesis of thus far inaccessible bromo vinyl triflimides is presented. Our previously reported concept of assisted vinyl cation formation was engaged to achieve both a protonation of relatively electron poor bromo alkynes and a reaction with high regio- and stereoselectivity. To the best of our knowledge, this is the first stereoselective addition of an N-nucleophile to an open β-halovinyl cation.

Chemo- And regioselective click reactions through nickel-catalyzed azide-alkyne cycloaddition

Metal-catalyzed cycloaddition is an expeditious synthetic route to functionalized heterocyclic frameworks. However, achieving reactivity-controlled metal-catalyzed azide-alkyne cycloadditions from competing internal alkynes has been challenging. Herein, we report a nickel-catalyzed [3 + 2] cycloaddition of unsymmetrical alkynes with organic azides to afford functionalized 1,2,3-triazoles with excellent regio- and chemoselectivity control. Terminal alkynes and cyanoalkynes afford 1,5-disubstituted triazoles and 1,4,5-trisubstituted triazoles bearing a 4-cyano substituent, respectively. Thioalkynes and ynamides exhibit inverse regioselectivity compared with terminal alkynes and cyanoalkynes, affording 1,4,5-trisubstituted triazoles with 5-thiol and 5-amide substituents, respectively. Density functional theory calculations are performed for the elucidation of the reaction mechanism. The computed mechanism suggests that a nickellacyclopropene intermediate is generated by the oxidative addition of the alkyne substrate to the Ni(0)-Xantphos catalyst, and the subsequent C-N coupling of this intermediate with an azide is responsible for the chemo- and regioselectivity.