(TRIMETHYLSILYL)DIAZOMETHANE

(TRIMETHYLSILYL)DIAZOMETHANE Basic information

Product Name:	(TRIMETHYLSILYL)DIAZOMETHANE
Synonyms:	(TRIMETHYLSILYL)DIAZOMETHANE;(Trimethylsilyl)diazomethane, ca. 2.0M solution in hexanes, tech.;Trimethylsilyldiazomethane,10%inhexane;TRIMETHYLSILYLDIAZOMETHANE, 1.0M IN METHYLENE CHLORIDE;（Trimethylsilyl)diazomethane solution 2M;(TRIMETHYLSILYL)DIAZOMETHANE, 2.0 M IN &;(Trimethylsilyl)diazomethane, 2M in hexanes;Trimethylsilyldiazomethane (ca. 10% in Hexane, ca. 0.60mol/L)
CAS:	18107-18-1
MF:	C4H10N2Si
MW:	114.22
EINECS:
Product Categories:	Analytical Chemistry;Diazomethane Precursors & Equivalents (GC Derivatizing Reagents);Esterification & Alkylation (GC Derivatizing Reagents);GC Derivatizing Reagents;Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry
Mol File:	18107-18-1.mol

(TRIMETHYLSILYL)DIAZOMETHANE Chemical Properties

Boiling point	96 °C
density	0.773 g/mL at 25 °C
refractive index	1.4362
Fp	−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 Information

Provider	Language
ACROS	English
SigmaAldrich	English

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

(TRIMETHYLSILYL)DIAZOMETHANE Preparation Products And Raw materials

Raw materials	Diethyl ether-->Tetrahydrofuran-->Phosphorus oxychloride-->Acetone-->Hexane-->Magnesium-->Phenol-->Sodium azide-->N,N-Dimethylaniline-->1,2-Dibromoethane-->Diphenylphosphoryl azide-->Chloromethyltrimethylsilane-->Diphenyl chlorophosphate
Preparation Products	PYRETHRIN 2-->Dimethyl Glutarate-->4-Methoxystyrene-->2-bromo-1-(4-bromo-3-fluorophenyl)ethanone-->BENZOIC ACID,4-BROMO-2-METHYL-,METHYL ESTER

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

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