DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL

DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL Basic information
Product Name:DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL
Synonyms:MTDA;[(1-METHOXY-2-METHYL-1-PROPENYL)OXY]TRIMETHYLSILANE;1-METHOXY-2-METHYL-1-(TRIMETHYLSILOXY)PROPENE;DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL;METHYL TRIMETHYLSILYL DIMETHYLKETENE ACETAL;DIMETHYLKETENE METHYL;Silane,[(1-methoxy-2-methyl-1-propen-1-yl)oxy]trimethyl-;organosilicon monomer
CAS:31469-15-5
MF:C8H18O2Si
MW:174.31
EINECS:629-515-4
Product Categories:Monoalkoxysilanes;Si (Classes of Silicon Compounds);Silicon Compounds (for Synthesis);Si-O Compounds;Synthetic Organic Chemistry;Vinylsilanes, Allylsilanes
Mol File:31469-15-5.mol
DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL Structure
DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL Chemical Properties
Boiling point 35 °C15 mm Hg(lit.)
density 0.858 g/mL at 25 °C(lit.)
refractive index n20/D 1.415(lit.)
Fp 58 °F
storage temp. Inert atmosphere,Room Temperature
solubility freely sol organic solvents.
form clear liquid
color Colorless to Almost colorless
Specific Gravity0.858
Water Solubility Hydrolyzes in water.
Sensitive Moisture Sensitive
Hydrolytic Sensitivity8: reacts rapidly with moisture, water, protic solvents
BRN 1362893
Stability:Moisture and Acid Sensitive
CAS DataBase Reference31469-15-5(CAS DataBase Reference)
EPA Substance Registry SystemSilane, [(1-methoxy-2-methyl-1-propenyl)oxy]trimethyl- (31469-15-5)
Safety Information
Hazard Codes Xi
Risk Statements 10-36/37/38
Safety Statements 16-26-36
RIDADR UN 3271 3/PG 3
WGK Germany 3
10-21
TSCA Yes
HazardClass 3
PackingGroup III
HS Code 29319090
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL Usage And Synthesis
Chemical PropertiesClear colorless liquid
Physical propertiesbp 35 °C/15 mmHg; d 0.858 g cm?3.
Uses1-Methoxy-2-methyl-1-(trimethylsilyloxy) propene is widely used as functional equivalent of enolate of methyl isobutyrate; ester enolate surrogate in electrophilic reactions including alkylation, aldol reaction, Michael reaction, initiator for group transfer polymerization of acrylates, nitroarylation, oxidation, dimerization, and cycloadditions.
Uses1-Methoxy-2-methyl-1-(trimethylsiloxy)propene is used in the synthesis of chiral β-lactams by reacting with (S)-alkylidene(1-arylethyl)amines in the presence of titanium tetrachloride. It acts as a catalyst or initiator in the group-transfer polymerization. It is also used as a versatile reagent in conjugate addition4 and aldol reactions.
PreparationThe title compound is a prototypical ketene silyl acetal (KSA) that can been prepared by either of the two most commonly employed methods: (a) deprotonation of the |á-hydrogen of an ester followed by silylation (1),16 and (b) metal-catalyzed hydrosilylation of |á,|?-unsaturated esters(2).

31469-15-5 synthesis

Purification MethodsAdd Et2O, wash with cold H2O, dry (Na2SO4), filter, evaporate Et2O, and distil the oily residue in a vacuum. [Ainsworth et al. J Organometal Chem 46 59 1972.]
DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL Preparation Products And Raw materials
Preparation ProductsBoc-D-tert-Leucinol-->1-Cyclohexenyloxytrimethylsilane-->5-(1,1-Dimethylethyl)-2-hydroxy-α,α-dimethyl-4-nitro-benzeneacetic Acid Methyl Ester-->Carebastine Methyl Ester
2-(4-BROMOPHENYL)-1,3-DIOXOLANE 1-METHOXY-1-TRIMETHYLSILYLOXYPROPENE VINYLOXYTRIMETHYLSILANE 1-(2-TRIMETHYLSILOXYETHOXY)-1-TRIMETHYLSILOXY-2-METHYLPROPENE 2-METHYL-1-(TRIMETHYLSILOXY)-1-PROPENE DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL

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