[(1-methoxy-2-methylprop-1-en-1-yl)oxy]trimethylsilane

• ChemBase ID: 149193
• Molecular Formular: C8H18O2Si
• Molecular Mass: 174.31282
• Monoisotopic Mass: 174.10760635
• SMILES: CC(=C(OC)O[Si](C)(C)C)C
• Canonical SMILES: COC(=C(C)C)O[Si](C)(C)C
• InChI: InChI=1S/C8H18O2Si/c1-7(2)8(9-3)10-11(4,5)6/h1-6H3
• InChIKey: JNOGVQJEBGEKMG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1-methoxy-2-methylprop-1-en-1-yl)oxy]trimethylsilane
• IUPAC Traditional name: [(1-methoxy-2-methylprop-1-en-1-yl)oxy]trimethylsilane
• Synonyms: 1-Methoxy-1-trimethylsiloxy-2-methyl-1-propene; Methyl trimethylsilyl dimethylketene acetal; MTDA; (1-Methoxy-2-methyl-1-propenyloxy)trimethylsilane; 1-Methoxy-2-methyl-1-(trimethylsiloxy)propene; Methyl trimethylsilyl dimethylketene acetal; 1-Methoxy-2-methyl-1-(trimethylsiloxy)propene; ((1-Methoxy-2-methylprop-1-en-1-yl)oxy)trimethylsilane; (1-甲氧基-2-甲基-1-烯丙氧基)三甲基硅烷; 1-甲氧基-2-甲基-1-(三甲基硅氧基)丙烯; 甲基三甲基硅基二甲基乙烯酮缩二乙醇; 1-甲氧基-2-甲基-1-(三甲基硅氧基)丙烯

Database IDs

• CAS Number: 31469-15-5
• EC Number: 000-000-0
• MDL Number: MFCD00010232
• Beilstein Number: 1362893
• PubChem SID: 24883797; 162243361; 24856589
• PubChem CID: 552336

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.8017
• LogD (pH = 7.4): 2.8017
• Log P: 2.8017
• Molar Refractivity: 54.0646 cm^3
• Polarizability: 19.539488 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 35 °C/15 mmHg(lit.); 35-36°C/15mm
• Flash Point: 30 °C; 30°C(86°F); 86 °F
• Density: 0.858; 0.858 g/mL at 25 °C(lit.)
• Refractive Index: 1.4150; n20/D 1.415(lit.); n20/D 1.416

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• UN Number: 3271; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-36/37/38
• Safety Statements: 16-26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3271 3/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (GC); 95%; 95+%; 97%
• Grade: technical
• Linear Formula: (CH3)2C=C(OCH3)OSi(CH3)3

DETAILS

Sigma Aldrich - 274585

Application
Group-transfer polymerization catalyst1,2 or initiator.3 Versatile reagent used in conjugate addition4 and aldol reactions.5,6
Packaging
5, 25, 100 g in glass bottle

Sigma Aldrich - 65098

Other Notes
This important ketene silyl acetal reacts under Lewis acid catalysis with various electrophiles 1,2,3

REFERENCES

• Silyl ketene acetal. The silyl enol ether of methyl isobutyrate. Catalyst for the initiation of group transfer polymerization, for controlled polymerization of ɑ?-unsaturated esters, ketones, nitriles and amides, in which the ketene acetal function is transferred along the growing polymer chain: J. Am. Chem. Soc., 105, 5706 (1983); Science, 222, 39 (1983).
• In the presence of a Lewis acid e.g. TiCl₄ or TMS-OTf, undergoes the Mukaiyama aldol reaction with aldehydes to give methyl ɑɑ-dimethyl-?-hydroxy esters: Chem. Lett., 989 (1975); Synth. Commun., 13, 449 (1983). Excellent results are obtained in these reactions with lanthanide triflates, e.g. Yb(OTf)₃, as catalysts: Synthesis, 371 (1993).
• With imines, gives ?-amino esters or ?-lactams according to conditions: Tetrahedron Lett., 3643 (1977); Chem. Lett., 1397 (1989); Tetrahedron, 44, 4157 (1988).
• Michael additions to enones, catalyzed by Yb(OTf)₃, have also been reported: Tetrahedron Lett., 33, 6815 (1992).