235040
1-Phenyl-1-trimethylsiloxyethylene
98%
Synonym(s):
α-(Trimethylsiloxy)styrene, Acetophenone enol trimethylsilyl ether
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About This Item
Linear Formula:
C6H5C(=CH2)OSi(CH3)3
CAS Number:
Molecular Weight:
192.33
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
237-308-1
Beilstein/REAXYS Number:
1306914
MDL number:
Assay:
98%
Form:
liquid
vapor density
>1 (vs air)
Quality Level
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.)
functional group
phenyl
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
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
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
168.8 °F - closed cup
flash_point_c
76 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
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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)
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 235040-25G | 04061838784896 |
| 235040-5G | 04061837007026 |