99337-17-4

Basic information

• Product Name: 2-(4-chlorophenyl)-3-(trimethylsilyl)-(Z)-prop-2-enenitrile
• Synonyms: 2-(4-chlorophenyl)-3-(trimethylsilyl)-(Z)-prop-2-enenitrile
• CAS NO: 99337-17-4
• Molecular Weight: 235.788
• Mol File: 99337-17-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-(4-chlorophenyl)-3-(trimethylsilyl)-(Z)-prop-2-enenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-chlorophenyl)-3-(trimethylsilyl)-(Z)-prop-2-enenitrile(99337-17-4)
• EPA Substance Registry System: 2-(4-chlorophenyl)-3-(trimethylsilyl)-(Z)-prop-2-enenitrile(99337-17-4)

Safety Data

• Hazardous Substances Data: 99337-17-4(Hazardous Substances Data)

Upstream product

• 873-73-4 4-n-chlorophenylacetylene 
• 7677-24-9 trimethylsilyl cyanide 

Relevant articles and documents

Palladium- and Nickel-Catalyzed Reaction of Trimethylsilyl Cyanide with Acetylenes. Addition of Trimethylsilyl Cyanide to the Carbon-Carbon Triple Bonds

The reaction of trimethylsilyl cyanide (1) with acetylenes in the presence of a transition-metal complex was investigated.The structures of starting acetylenes and catalysts and both amounts of solvent and 1 highly affected product distributions.The PdCl2/pyridine catalyzed reaction of phenylacetylene and para-substituted phenylacetylenes with 1 resulted in the addition of 1 to the carbon-carbon triple bonds to give cyano-substituted vinylsilanes in good to high yields with high regio- and stereoselectivity.Ortho-substituted phenylacetylenes gave addition products less stereoselectively.Stereoselectivity affording Z adducts decreased in the order of para- meta- ortho-substituted phenylacetylenes.The NiCl2/DIBAH-catalyzed reaction of arylacetylenes was less stereoselective regardless of substitution patterns of arylacetylenes used.When the nickel-catalyzed reaction of arylacetylenes was run without solvent using an excess amount of 1, 5-amino-1H-pyrrole-2-carbonitriles were obtained as a single product, instead of the above simple addition products.The reaction of terminal aliphatic acetylenes with 1 also gave addition products with moderate stereoselectivity.Internal acetylenes gave complex mixtures including addition products and/or pyrrole derivatives.Diarylacetylenes afforded 5-amino-1H-pyrrole-2-carbonitriles selectively in the presence of a palladium or nickel catalyst (without solvent and an excess amount of 1).Intramolecular cyclization of a 1,6-diyne was also studied.