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Sigma-Aldrich

1-Phenyl-1-trimethylsiloxyethylene

98%

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Synonym(s):
α-(Trimethylsiloxy)styrene, Acetophenone enol trimethylsilyl ether
Linear Formula:
C6H5C(=CH2)OSi(CH3)3
CAS Number:
13735-81-4
Molecular Weight:
192.33
Beilstein/REAXYS Number:
1306914
EC Number:
237-308-1
MDL number:
MFCD00008582
UNSPSC Code:
12352100
PubChem Substance ID:
24854075
NACRES:
NA.22

vapor density

>1 (vs air)

Quality Level

100

assay

98%

form

liquid

refractive index

n20/D 1.502 (lit.)

bp

88-89 °C/11 mmHg (lit.)

density

0.938 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C[Si](C)(C)OC(=C)c1ccccc1

InChI

1S/C11H16OSi/c1-10(12-13(2,3)4)11-8-6-5-7-9-11/h5-9H,1H2,2-4H3

InChI key

AFFPCIMDERUIST-UHFFFAOYSA-N

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General description

1-Phenyl-1-trimethylsiloxyethylene is a styrene type silyl enol ether, reacts with formaldehyde and 2,4-pentanedione to yield the corresponding dihydropyran. It also undergoes Mukaiyama aldol reaction with aldehydes in water in the presence of amphiphilic calix[6]arene derivatives as surfactants.

Application

1-Phenyl-1-trimethylsiloxyethylene has been used in the synthesis of:
  • β-amino ketones in water via Mannich-type reaction
  • cis-2,6-disubstituted dihydropyrans via three-component, one-pot cascade reaction

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Novel one-pot Mannich-type reaction in water: indium trichloride-catalyzed condensation of aldehydes, amines and silyl enol ethers for the synthesis of ?-amino ketones and esters.
Loh T-P and Wei L-L.
Tetrahedron Letters, 39(3), 323-326 (1998)
Robert J Hinkle et al.
Tetrahedron, 65(34), 6834-6839 (2010-02-18)
The rapid synthesis of cis-2,6-disubstituted dihydropyrans is achieved in a three-component, one-pot cascade reaction. BiBr(3)-ediated addition of ketene silyl acetals or silyl enol ethers to beta,gamma-unsaturated cis-4-trimethylsilyl-3-butenal provides a Mukaiyama aldol adduct containing a vinylsilane moiety tethered to a silyl
Calix [6] arene derivatives bearing sulfonate and alkyl groups as surfactants in Sc (OTf)3-catalyzed Mukaiyama aldol reactions in water.
Tian H-Y, et al.
Tetrahedron Letters, 41(15), 2529-2532 (2000)
Catalyst-free aqueous multicomponent domino reactions from formaldehyde and 1, 3-dicarbonyl derivatives.
Gu Y, et al.
Green Chemistry, 11(12), 1968-1972 (2009)

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