(TRIMETHYLSILYL)DIAZOMETHANE Property

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

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)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H302Harmful if swallowed

H304May be fatal if swallowed and enters airways

H315Causes skin irritation

H330Fatal if inhaled

H331Toxic if inhaled

H336May cause drowsiness or dizziness

H350May cause cancer

H361Suspected of damaging fertility or the unborn child

H370Causes damage to organs

H373May cause damage to organs through prolonged or repeated exposure

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

(TRIMETHYLSILYL)DIAZOMETHANE Chemical Properties,Usage,Production

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.