30718-17-3

Usage

Uses

Used in Chemical Synthesis:
TRIMETHYLSILYLMETHYL ISOCYANIDE is used as a reagent for the preparation of isocyanomethylenetriphenylphosphorane. This application is due to its ability to react with protic nucleophiles, making it a valuable component in the synthesis of various organic compounds.
Used in the Preparation of Insertion Products:
In the field of organometallic chemistry, TRIMETHYLSILYLMETHYL ISOCYANIDE is used as a reactant for the reaction with (η2-formaldehyde)zirconocene complex. This reaction results in the formation of insertion products, which are important for further chemical transformations and the development of new materials.
Overall, TRIMETHYLSILYLMETHYL ISOCYANIDE plays a significant role in the chemical industry, particularly in the synthesis of complex organic compounds and the development of novel materials. Its unique reactivity and versatility make it a valuable asset in the field of chemical research and development.

InChI:InChI=1/C5H11NSi/c1-6-5-7(2,3)4/h5H2,2-4H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 33742-77-7 isocyanomethyllithium 
• 593-75-9 methyl isocyanate 

Downstream Products

• 75-76-3 tetramethylsilane 
• 85236-99-3 N-Trimethylsilanylmethyl-thioformimidic acid phenyl ester 
• 94714-36-0 VUF 5512 
• 51746-85-1 3-(1H-imidazol-4-yl)pyridine 
• 120118-99-2 4-(thiophen-2-yl)-1H-imidazole 
• 918534-44-8 C₁₆H₂₅N₅O 
• 823835-01-4 (pyridine)Rh(5,10,15,20-tetramesitylporphyrinato)CN 
• 915085-32-4 [Rh(meso-tetramesitylporphyrinato)(CN)(CNCH₂SiMe₃)] 
• 1280185-50-3 2-(4-chlorophenyl)-2-(3-cyano-2-oxo-4-phenylquinolin-1(2H)-yl)-N-((trimethylsilyl)methyl)acetamide 
• 317339-19-8 4⁽⁵⁾-(cyclohexene-4-ylmethyl) imidazole 
• 58650-48-9 4-isopropyl-1H-imidazole 

Relevant academic research and scientific papers

Synthesis of Vinyl Isocyanides and Development of a Convertible Isonitrile

The reaction of isocyanomethylenetriphenylphosphorane, generated in situ from the corresponding phosphonium salt, with a diverse set of aldehydes afforded vinyl isocyanides in good to high yields. Excellent E-selectivity was observed for aliphatic aldehydes and 2,6-disubstituted aromatic aldehydes, whereas Z-olefins were formed predominantly with ortho-substituted aryl aldehydes. (Z)-1-Bromo-2-(2-isocyanovinyl)benzene (5l) was found to be a truly universal isonitrile since, after Ugi reaction, the resulting secondary amide unit (RNHCO-) is convertible under both acidic and basic conditions. The application of 5l in the synthesis of polyheterocycles is also illustrated.

Process for the synthesis of imidazoles

The present invention provides a process for the preparation of imidazoles by reacting a cyano compound with a silylalkylisocyanide compound. Such imidazoles are useful pharmacologically-active compounds and/or intermediates for the preparation of pharmacologically-active compounds.

AN IMPROVED SYNTHESIS OF TRIMETHYLSILYLMETHYL ISOCYANIDE

Trimethylsilylmethyl isocyanide is prepared by a new method which gives a higher overall yield and circumvents the use of methyl isocyanide.

Alkaloid synthesis via the intramolecular imidate methylide 1,3-dipolar cycloaddition reaction

A concise synthesis for the neurotoxic physostigmine alkaloid d,l-eserethole is described which relys upon an intramolecular cycloaddition reaction involving a "non-stabilized" imidate methylide and an unactivated alkene. The facility of this cyclization

The Direct Generation of N-Acyl Formimidate Methylides. An Efficient Approach to the Synthesis of Pyrrolidine Derivatives

The reaction of silyl-formamidines and silyl-thioformimidates with acyl fluorides gives N-acyl imidate methylides which have been successfully trapped with several dipolarophiles to afford pyrrolidine derivatives in high yields.