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Merck
CN

376078

(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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24863419
EC Number:
217-393-1
Beilstein/REAXYS Number:
1849023
MDL number:
MFCD00042845
Assay:
≥85%
Form:
liquid

Key Documents

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InChI key

UAIFZYSPVVBOPN-UHFFFAOYSA-N

InChI

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

SMILES string

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

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

Quality Level

100

Related Categories

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

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

19.4 °F - closed cup

flash_point_c

-7 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
0000468959
0000468959
0000409163
0000409163
SHBN4760

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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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