212505-57-2

Basic information

• Product Name: N-(2-iodobenzylidene)-2-methylpropan-2-amine
• Synonyms: N-(2-iodobenzylidene)-2-methylpropan-2-amine
• CAS NO: 212505-57-2
• Molecular Weight: 287.143
• Mol File: 212505-57-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(2-iodobenzylidene)-2-methylpropan-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-iodobenzylidene)-2-methylpropan-2-amine(212505-57-2)
• EPA Substance Registry System: N-(2-iodobenzylidene)-2-methylpropan-2-amine(212505-57-2)

Safety Data

• Hazardous Substances Data: 212505-57-2(Hazardous Substances Data)

Upstream product

• 26260-02-6 2-iodobenzaldehyde 
• 75-64-9 tert-butylamine 

Downstream Products

• 7661-42-9 3-n-butylisoquinoline 
• 67237-85-8 3-(4-chlorophenyl)isoquinoline 
• 1383549-86-7 3-(4-fluorophenyl)isoquinoline 
• 20435-81-8 3-(4-methoxyphenyl)isoquinoline 
• 67237-87-0 3-(4-methylphenyl)isoquinoline 
• 37993-76-3 3-phenylisoquinoline 
• 109802-64-4 ethyl 3-phenylisoquinoline-4-carboxylate 
• 385416-19-3 4-hydroxymethyl-3-phenylisoquinoline 
• 385416-18-2 4-ethyl-3-phenylisoquinoline 
• 320371-82-2 3,4-bis(4-methoxyphenyl)isoquinoline 
• 55150-54-4 1-chloro-3-phenylisoquinoline 
• 51787-71-4 3-phenylisoquinoline 2-oxide 
• 52839-45-9 3,4-diphenylisoquinoline 

Relevant articles and documents

Synthesis of isoquinolines and pyridines by the palladium/copper-catalyzed coupling and cyclization of terminal acetylenes and unsaturated imines: The total synthesis of decumbenine B

Monosubstituted isoquinolines and pyridines have been prepared in good to excellent yields via coupling of terminal acetylenes with the tert-butylimines of o-iodobenzaldehydes and 3-halo-2-alkenals in the presence of a palladium catalyst and subsequent copper-catalyzed cyclization of the intermediate iminoalkynes. In addition, isoquinoline heterocycles have been prepared in excellent yields via copper-catalyzed cyclization of iminoalkynes. The choice of cyclization conditions is dependent upon the nature of the terminal acetylene that is employed, as only aryl and alkenyl acetylenes cyclize under the palladium-catalyzed reaction conditions that have been developed. However, aryl-, vinylic-, and alkyl-substituted acetylenes undergo palladium-catalyzed coupling and subsequent copper-catalyzed cyclization in excellent yields. The total synthesis of the isoquinoline natural product decumbenine B has been accomplished in seven steps and 20% overall yield by employing this palladium-catalyzed coupling and cyclization methodology.

Highly Regioselective Isoquinoline Synthesis via Nickel-Catalyzed Iminoannulation of Alkynes at Room Temperature

A simple and cost-efficient nickel catalytic system for the annulation of 2-haloaldimines with alkynes to synthesize 3,4-disubstituted and 3-substituted isoquinolines at room temperature has been developed. The air-stable and inexpensive Ni(dppe)Cl2 was employed as a precatalyst, and Et3N was found to be an essential additive for obtaining high yields. By using this nickel catalytic system one-pot three-component direct synthesis of isoquinolines starting with simple 2-halobenzaldehydes, tert-butylamine, and alkynes were also achieved. These reactions occur in moderate to excellent yields with complete regioselectivity. Moreover, these reactions feature a broad substrate scope, easy scalability, operational simplicity, and excellent practicality.