(TRIMETHYLSILYL)DIAZOMETHANE Chemical Properties

Boiling point:

96 °C

Density 

0.773 g/mL at 25 °C

refractive index 

1.4362

Flash point:

−31 °F

storage temp. 

Refrigerator

solubility 

Sol most organic solvents; insol H2O.

form 

Solution

color 

White

Water Solubility 

Immiscible with water. Miscible with organic solvents.

Sensitive 

Moisture & Light Sensitive

BRN 

1902903

Stability:

Shock Sensitive

CAS DataBase Reference

18107-18-1(CAS DataBase Reference)

EPA Substance Registry System

Silane, (diazomethyl)trimethyl- (18107-18-1)

Safety Information

Hazard Codes 

F+,Xn,N,F,T,T+

Risk Statements 

12-19-22-66-67-65-62-51/53-48/20-38-11-23-39/26-26-45

Safety Statements 

9-16-29-33-36/37-61-62-45-28-53

RIDADR 

UN 1208 3/PG 2

WGK Germany 

3

F 

10

TSCA 

Yes

HazardClass 

3

PackingGroup 

II

HS Code 

29270000

Hazardous Substances Data

18107-18-1(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

(TRIMETHYLSILYL)DIAZOMETHANE Usage And Synthesis

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

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

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

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.

(TRIMETHYLSILYL)DIAZOMETHANE(18107-18-1)Related Product Information

• 2-METHOXYPHENYLMAGNESIUM BROMIDE
• DIMETHYLALUMINUM CHLORIDE
• Chloromethane
• 4-ETHYLPHENYLMAGNESIUM BROMIDE
• 4-THIOANISOLEMAGNESIUM BROMIDE
• Tricyclohexyl phosphine
• 3-(DIMETHYLAMINO)PROPYL CHLORIDE HYDROCHLORIDE
• (TRIMETHYLSILYL)METHYLLITHIUM
• P-TOLYLMAGNESIUM CHLORIDE
• 4-Methoxyphenylmagnesium bromide
• HEXANES
• Hexane
• TRIMETHYLSILANE
• Diazomethane
• (TRIMETHYLSILYL)DIAZOMETHANE