CAS 31469-15-5 Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl- (HCID 552336)

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Basic information

CAS: 31469-15-5
Standard SMILES: COC(O[Si](C)(C)C)=C(C)C
InChIKey: JNOGVQJEBGEKMG-UHFFFAOYSA-N
Molecular formula: C8H18O2Si
Average molar mass: 174.31 g/mol
Monoisotopic mass: 174.10760635

Names & identifiers

Preferred name: Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-
IUPAC: (1-methoxy-2-methylprop-1-enoxy)-trimethylsilane
English name: Dimethylketene methyl trimethylsilyl acetal
Molecular formula: C8H18O2Si
Molecular weight: 174.31

Names & synonyms

31469-15-5Silane, [(1-methoxy-2-methyl-1-propenyl)oxy]trimethyl-Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-DTXSID3073470RefChem:1098511DTXCID2038366Dimethylketene Methyl Trimethylsilyl Acetal1-Methoxy-2-methyl-1-(trimethylsiloxy)propeneMethyl trimethylsilyl dimethylketene acetal((1-Methoxy-2-methylprop-1-en-1-yl)oxy)trimethylsilane(1-methoxy-2-methylprop-1-enoxy)-trimethylsilane1-Methoxy-1-(trimethylsiloxy)-2-methyl-1-propene

Show more names

MTDA(1-Methoxy-2-Methylprop-1-enyloxy)triMethylsilaneDKSI044DKFELEX00861-Methoxy-1-triorganosilicon monomerDIMETHYLKETENE METHYL

MFCD00010232Dimethylketene methyltrimethylsilylacetal(1-Methoxy-2-methyl-1-propenyloxy)trimethylsilane[(1-methoxy-2-methylprop-1-en-1-yl)oxy]trimethylsilaneS07264(1-Methoxy-2-methylprop-1-enoxy)trimethylsilaneMethyl trimethylsilyl dimethylketene acetal, 95%(1-methoxy-2-methyl-prop-1-enoxy)-trimethyl-silane

Properties

Computed structural properties

Topological polar surface area: 18.5 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 3
Heavy atoms: 11
Formal charge: 0
Complexity: 152

Physicochemical properties

Boiling point: 35 °C15 · 35 °C15 mm Hg(lit.)
Density: 0.858 g/mL · 0.858 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.415(lit.)
Flash point: 58 °F · 58 °F
storage temp.: Inert atmosphere,Room Temperature
solubility: freely sol organic solvents.
form: clear liquid
color: Colorless to Almost colorless
Specific Gravity: 0.858 · 0.858
Water Solubility: Hydrolyzes in water.
Sensitive: Moisture Sensitive
Hydrolytic Sensitivity: 8 · 8: reacts rapidly with moisture, water, protic solvents
BRN: 1362893 · 1362893
Stability: Moisture and Acid Sensitive
InChI: 1S/C8H18O2Si/c1-7(2)8(9-3)10-11(4,5)6/h1-6H3
InChIKey: JNOGVQJEBGEKMG-UHFFFAOYSA-N

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationPMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Hazard Classes and CategoriesFlam. Liq. 3 (100%)

Safety data

F: 10-21
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
ridadr: UN 3271 3/PG 3
hs_code: 29319090
risk_code: 10-36/37/38
Signal word: Warning
Symbol(GHS): GHS02,GHS07
hazard_code: Xi
safety_code: 16-26-36
hazard_class: 3
Storage Class: 3 - Flammable liquids
packing_group: III
target organs

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationSilane, [(1-methoxy-2-methyl-1-propen-1-yl)oxy]trimethyl-: ACTIVE

Applications · 2 items

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.

Preparation methods · 1 item

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).