TRIMETHYLSILYL ISOTHIOCYANATE

Chemical properties

clear colorless to light yellow liquid

The Uses of TRIMETHYLSILYL ISOTHIOCYANATE

Trimethylsilyl isothiocyanate is used as derivatizing reagent during the synthesis of amino acid thiohydantoins. It participates in ring opening reaction of N-substituted aziridines and cyclohexene oxide.

The Uses of TRIMETHYLSILYL ISOTHIOCYANATE

Trimethylsilyl isothiocyanate was used as derivatizing reagent during the synthesis of amino acid thiohydantoins.

General Description

Trimethylsilyl isothiocyanate (TMS-ITC) reacts with fullerene-mixed peroxide C₆₀(O)(OOtBu)₄ to yield isothiocyanate derivative C₆₀(NCS)(OH)(OOtBu)₄. TMS-ITC undergoes condensation with ethyl 2-benzylamino-5-methyl-3-phenylcyclopent-1-enecarboxylate to yield 1-benzyl-5-methyl-7-phenyl-2-thioxo-1,2,3,5,6,7-hexahydrocyclopentapyrimidin-4-one. It participates in ring opening reaction of N-substituted aziridines and cyclohexene oxide.

Purification Methods

The 1H NMR spectrum should have only one peak; if not purify it by repeated fractionation in an all-glass system using a 50cm (4mm internal diameter) column without packing. [Anderson J Am Chem Soc 69 3049 1947, Fehér & Blümcke Chem Ber 90 1934 1957, Neidleim & Hege Synthesis 51 1975, Beilstein 4 III 1861, 4 IV 4011.]