CAS 30718-17-3, Cat. No EN300-7579882
Reagent for heterocyclization, formamidines and thioformimidates synthesis
Trimethylsilylmethyl isocyanide is a versatile reagent used in [3+2] cycloaddition and nucleophilic insertion reactions. It enables the acid-catalyzed synthesis of 1-substituted tetrazoles through reaction with trimethylsilyl azide (TMSN3), avoiding hazardous hydrazoic acid1. The reagent also undergoes Cu-catalyzed insertion with amines and thiols to form formamidines and thioformimidates, useful in medicinal chemistry2. Additionally, it participates in nucleophilic substitutions with alcohols and carbanions, expanding its synthetic utility. Volatile and air-sensitive, it requires anhydrous storage to maintain stability. Its broad functional group compatibility makes it a valuable tool in heterocyclic and medicinal chemistry.
Synonyms: (trimethylsilyl)methyl isocyanide; isocyanomethyl(trimethyl)silane; (isocyanomethyl)trimethylsilane; silane, (isocyanomethyl)trimethyl-; TMS methyl isocyanide
Selected publications
-
Synthesis of 1-Substituted Tetrazoles via the Acid-Catalyzed [3+2] Cycloaddition between Isocyanides and Trimethylsilyl Azide.
Jin T.; Kamijo S.; Yamamoto Y. Tetrahedron Lett 2004, 45 (51), 9435–9437. DOI: 10.1016/j.tetlet.2004.10.103
-
An Improved Synthesis of Trimethylsilylmethyl Isocyanide and Some of Its Reactions with Nucleophiles.
Smith R.; Livinghouse T. Synth Commun 1984, 14 (7), 639–646. DOI: 10.1080/00397918408063749