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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

JAN Code

376078-1G:
376078-BULK:
376078-VAR:
376078-5G:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN4760
47596TJV
47596TJ
50196DJ
14308PN

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Sigma-Aldrich

174645

2-Methoxypropene

Hexamethyldisiloxane puriss., ≥98.5% (GC)

Sigma-Aldrich

52630

Hexamethyldisiloxane

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.
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)

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