(TRIMETHYLSILYL)DIAZOMETHANE

Chemical properties

clear yellow solution

Physical properties

bp 96 °C/775 mmHg; nD/25 1.4362.2

The Uses of (TRIMETHYLSILYL)DIAZOMETHANE

(Trimethylsilyl)diazomethane is used as an analyte in the determination of some phenolic organohalogens in human serum by GC-MS.

The Uses of (TRIMETHYLSILYL)DIAZOMETHANE

Trimethylsilyldiazomethane (2.0M in hexane, 25 mL, 50 mmol) was added dropwise to a 0 C solution of the SM (4.64 g, 41.4 mmol) in DCM (25 mL) and MeOH (5 mL). The reaction mixture was stirred at RT for 30 min. The mixture was quenched with AcOH (0.45 mL) and concentrated in vacuo. The resulting material was purified by silica gel chromatography (20% DCM/hexane) to provide the product as a colorless oil. [3.8 g, 73%]

The Uses of (TRIMETHYLSILYL)DIAZOMETHANE

Reactant for preparation of: &bull Macrolactam analogs of the natural product macrolide (-)-A26771B with improved metabolic stability and antibacterial activity &bull Aigialomycin D analogues as protein kinase inhibitors for cancer treatment &bull Unnatural α-amino acid derivatives containing gem-bisphosphonates via Michael addition reaction &bull Capped 4-methylumbelliferyl hyaluronan disaccharides and tetrasaccharides as potential hyaluronidase substrates &bull Stictamides A-C as matrix metallopeptidase 12 (MMP12) inhibitors with antitumor invasion activity &bull Endothelin converting enzyme (ECE) Inhibitors WS 75624A and WS 75624B via a cross-metathesis approach &bull Ent-kaurene derivatives as anti-inflammatory agents &bull Desmosdumotin C analogs as potent antitumor agents acting via activation of spindle assembly checkpoint &bull Imidazolo[2,1-b]benzothiazole derivatives as potential p53 inhibitors

The Uses of (TRIMETHYLSILYL)DIAZOMETHANE

Trimethylsilyldiazomethane is used as one-carbon homologation reagent; stable, safe substitute for diazomethane;participating in the synthesis reactions of insertion reactions;ketenylation reactions;preparation of homoallylic sulfides;pericyclic reactions;[C-N-N] 1,3-dipole for the preparation of azoles.

Preparation

Trimethylsilyldiazomethane is prepared by the diazo-transfer reaction of trimethylsilylmethylmagnesium chloride with diphenyl phosphorazidate (DPPA) (eq 1).

General Description

(Trimethylsilyl)diazomethane is considered as a non-explosive substitute to diazomethane for the homologation of carbonyl derivatives, mainly ketones, via reactions such as Tiffeneau-Demjanov rearrangement.