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(Iodomethyl)trimethylsilane is used for the N-alkylation of amides, in a reaction sequence to prepare unstabilized ylides for [2+3]-cycloadditions. It can react with acetoacetic acid ethyl ester to get 3-trimethylsilanyl-proπonic acid ethyl ester.
Motoo Tori.; Chiho Makino.; Kenji Hisazumi.; Masakazu Sono.; Katsuyuki Nakashima. Synthesis of a homochiral ketone having a pinguisane skeleton using phenylethylamine as a chiral auxiliary: a formal total synthesis of deoxopinguisone. Tetrahedron: Asymmetry. 2001, 12, (2), 301-307.
Dale L. Boger.; Louis R. Cerbone.; Daniel Yohannes. Oxidative coupling of methyl 6-hydroxyindole-2-carboxylate with primary amines. Preparation of 2-substituted methyl pyrrolo[2,3-e]benzoxazole-5-carboxylates. J. Org. Chem. 1988, 53, (21), 5163-5166.
Hazard Statements: H226-H315-H319-H335
Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P260-P201-P280g-P304+P340-P405-P501a
Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Wear protective gloves. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.