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227226

Sigma-Aldrich

1-(Trimethylsiloxy)-1,3-butadiene

98%

Synonym(s):

(1,3-Butadien-1-yloxy)trimethylsilane, (1,3-Butadienyloxy)trimethylsilane, (Butadienyloxy)trimethylsilane, 1-(Trimethylsiloxy)butadiene, 1-[(Trimethylsilyl)oxy]-1,3-butadiene, 1-[(Trimethylsilyl)oxy]butadiene

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About This Item

Linear Formula:
(CH3)3SiOCH=CHCH=CH2
CAS Number:
6651-43-0
Molecular Weight:
142.27
Beilstein:
1902024
MDL number:
MFCD00009647
UNSPSC Code:
12352100
PubChem Substance ID:
24853620
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.448 (lit.)

bp

131 °C (lit.)

density

0.811 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C7H14OSi/c1-5-6-7-8-9(2,3)4/h5-7H,1H2,2-4H3/b7-6+

InChI key

UQGOYQLRRBTVFM-VOTSOKGWSA-N

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General description

Mechanism of Diels-Alder reaction between 1-(trimethylsiloxy)-1,3-butadiene and 4,6-dinitrobenzofuroxan has been studied using state-of-the-art computational methods.

Application

1-(Trimethylsiloxy)-1,3-butadiene is commonly employed as diene in the Diels-Alder reaction.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

77.0 °F - closed cup

Flash Point(C)

25 °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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Sigma-Aldrich

235040

1-Phenyl-1-trimethylsiloxyethylene

Mats Linder et al.
Organic letters, 14(1), 118-121 (2011-12-01)
The stepwise Diels-Alder reaction between 1-trimethylsiloxy-1,3-butadiene and 4,6-dinitrobenzofuroxan is explored using state-of-the-art computational methods. The results support a stepwise mechanism via a persistent intermediate, however, not the one previously reported (Lakhdar et al., Chem. Eur. J.2007, 16, 5681) but a

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