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Sigma-Aldrich

2-(Trimethylsiloxy)-1,3-cyclohexadiene

95%

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About This Item

Empirical Formula (Hill Notation):
C9H16OSi
CAS Number:
54781-19-0
Molecular Weight:
168.31
Beilstein:
2079140
MDL number:
MFCD00274202
UNSPSC Code:
12352100
PubChem Substance ID:
24866492
NACRES:
NA.22

Assay

95%

form

liquid

refractive index

n20/D 1.462 (lit.)

bp

65 °C/7 mmHg (lit.)

density

0.899 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C[Si](C)(C)OC1=CCCC=C1

InChI

1S/C9H16OSi/c1-11(2,3)10-9-7-5-4-6-8-9/h5,7-8H,4,6H2,1-3H3

InChI key

WPIRVUXAMPRMAY-UHFFFAOYSA-N

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General description

2-(Trimethylsiloxy)-1,3-cyclohexadiene ((cyclohexa-1,5-dien-1-yloxy)trimethylsilane) is silyl enol ether of cyclohexenone. The Diels–Alder reactions with dienophiles α-acetoxyacrylonitrile, acrylonitrile and α-chloroacrylonitrile has been studied.

Application

2-(Trimethylsiloxy)-1,3-cyclohexadiene may be used as a diene in the synthesis of isoquinuclidinone 2-aza[2.2.2]octa-3,5-dione by reacting with p-toluenesulfonyl cyanide.

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

116.6 °F - closed cup

Flash Point(C)

47 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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High-Temperature Diels-Alder Reactions: Transfer from Batch to Continuous Mode.
Abele S, et al.
Organic Process Research & Development, 16(5), 1114-1120 (2011)
Safety Assessment of Diels-Alder Reactions with Highly Reactive Acrylic Monomers.
Abele S, et al.
Organic Process Research & Development, 16(12), 2015-2020 (2012)
Cynthia K McClure et al.
The Journal of organic chemistry, 68(21), 8256-8257 (2003-10-11)
The hetero-Diels-Alder reaction of an electron-deficient nitrile, p-toluenesulfonyl cyanide, with the silyl enol ether of cyclohexenone produced a hydrolytically sensitive [4 + 2] adduct in good yield. Use of Mander's reagent, ethyl cyanoformate, with the same diene, produced an unstable
Design and Scale-Up of Diels-Alder Reactions for the Practical Synthesis of 5-Phenylbicyclo [2.2. 2] oct-5-en-2-one.
Funel JA, et al.
Organic Process Research & Development, 15(6), 1420-1427 (2011)

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