Chemical Properties
clear yellow solution
Physical properties
bp 96 °C/775 mmHg; nD/25 1.4362.2
Uses
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.
Uses
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
Uses
(Trimethylsilyl)diazomethane is used as an analyte in the determination of some phenolic organohalogens in human serum by GC-MS.
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.
