Skip to Content
Merck
CN

235040

1-Phenyl-1-trimethylsiloxyethylene

98%

Synonym(s):

α-(Trimethylsiloxy)styrene, Acetophenone enol trimethylsilyl ether

Sign In to View Organizational & Contract Pricing

Select a Size

About This Item

Linear Formula:
C6H5C(=CH2)OSi(CH3)3
CAS Number:
13735-81-4
Molecular Weight:
192.33
Beilstein:
1306914
EC Number:
237-308-1
MDL number:
MFCD00008582
UNSPSC Code:
12352100
PubChem Substance ID:
24854075
NACRES:
NA.22

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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.)

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

168.8 °F - closed cup

Flash Point(C)

76 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCBW6100
BCCK5140
BCBH9277V
1453069V
1453069

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
Catalyst-free aqueous multicomponent domino reactions from formaldehyde and 1, 3-dicarbonyl derivatives.
Gu Y, et al.
Green Chemistry, 11(12), 1968-1972 (2009)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service