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376078

Sigma-Aldrich

(Isopropenyloxy)trimethylsilane

≥85%

Synonym(s):

2-(Trimethylsiloxy)propene, Acetone enol trimethylsilyl ether, IPOTMS

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About This Item

Linear Formula:
CH3C(=CH2)OSi(CH3)3
CAS Number:
1833-53-0
Molecular Weight:
130.26
Beilstein:
1849023
EC Number:
217-393-1
MDL number:
MFCD00042845
UNSPSC Code:
12352100
PubChem Substance ID:
24863419
NACRES:
NA.22

Assay

≥85%

form

liquid

impurities

10-15% hexamethyldisiloxane

refractive index

n20/D 1.395 (lit.)

density

0.78 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

CC(=C)O[Si](C)(C)C

InChI

1S/C6H14OSi/c1-6(2)7-8(3,4)5/h1H2,2-5H3

InChI key

UAIFZYSPVVBOPN-UHFFFAOYSA-N

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General description

(Isopropenyloxy)trimethylsilane is an enol silyl ether. It participates as nucleophile in Lewis acid-promoted C3-nucleophile substitution of tetracyclic bromide. It is reported to participate in the total synthesis of (±)-powelline. It is reported to participate in dityltin bis(triflate) catalyzed Michael addition reaction of enol silyl ethers.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

19.4 °F - closed cup

Flash Point(C)

-7 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

174645

2-Methoxypropene

Hexamethyldisiloxane puriss., ≥98.5% (GC)

Sigma-Aldrich

52630

Hexamethyldisiloxane

Katherine M Bogle et al.
Organic letters, 12(6), 1252-1254 (2010-02-24)
The total synthesis of (+/-)-powelline (13 linear steps in an overall yield of 6%) and (+/-)-buphanidrine (14 linear steps and a 6% overall yield) and has been achieved using a novel approach to the crinane skeleton. An organocatalytic oxidative coupling
Organotin triflate as practical catalyst for Michael addition of enol silyl ethers.
Sato T, et al.
Tetrahedron, 47(47), 9773-9782 (1991)
Justin Kim et al.
Journal of the American Chemical Society, 133(38), 14940-14943 (2011-08-31)
Concise and enantioselective total syntheses of (+)-naseseazines A and B are described. Our regioselective and directed dimerization of diketopiperazines provides their critical C3-C(sp(2)) linkages, an assembly with plausible biogenetic relevance. We revise the absolute stereochemistry of (+)-naseseazines A and B.

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