Skip to Content
MilliporeSigma
Get 22% off for Pi Day through March 31.Save Now

212830

trans-1-Methoxy-3-trimethylsiloxy-1,3-butadiene

95%

Synonym(s):

Danishefsky’s diene

Slide 1 of 1
Sign In to View Organizational & Contract Pricing.

Select a Size

1 G

$65.70

5 G

$209.00

$65.70

Check Cart for Availability
​
Request a Bulk Order

About This Item

Linear Formula:
(CH3)3SiOC(=CH2)CH=CHOCH3
CAS Number:
54125-02-9
Molecular Weight:
172.30
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24852745
MDL number:
MFCD00008498
Beilstein/REAXYS Number:
1616761
Assay:
95%
Form:
liquid

Key Documents

View All Documentation

Skip To

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

assay

95%

form

liquid

impurities

2-5% 4-methoxy-3-buten-2-one

refractive index

n20/D 1.454 (lit.)

bp

68-69 °C/14 mmHg (lit.)

density

0.885 g/mL at 25 °C (lit.)

functional group

ether

storage temp.

2-8°C

SMILES string

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

InChI

1S/C8H16O2Si/c1-8(6-7-9-2)10-11(3,4)5/h6-7H,1H2,2-5H3/b7-6+

InChI key

SHALBPKEGDBVKK-VOTSOKGWSA-N

Related Categories

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
145491276030423424
trans-1-Methoxy-3-trimethylsiloxy-1,3-butadiene 95%

212830

trans-1-Methoxy-3-trimethylsiloxy-1,3-butadiene

2,3-Dimethyl-1,3-butadiene 98%, contains 100 ppm BHT as stabilizer

Sigma-Aldrich

145491

2,3-Dimethyl-1,3-butadiene

2,3-Dimethoxy-1,3-butadiene 95%

Sigma-Aldrich

276030

2,3-Dimethoxy-1,3-butadiene

2-(Trimethylsiloxy)-1,3-cyclohexadiene 95%

Sigma-Aldrich

423424

2-(Trimethylsiloxy)-1,3-cyclohexadiene

assay

95%

assay

98%

assay

95%

assay

95%

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

bp

68-69 °C/14 mmHg (lit.)

bp

68-69 °C (lit.)

bp

134-136 °C/745 mmHg (lit.)

bp

65 °C/7 mmHg (lit.)

density

0.885 g/mL at 25 °C (lit.)

density

0.726 g/mL at 25 °C (lit.)

density

0.94 g/mL at 25 °C (lit.)

density

0.899 g/mL at 25 °C (lit.)

form

liquid

form

liquid

form

liquid

form

liquid

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

General description

trans-1-methoxy-3-trimethylsiloxy-1,3-butadiene is a funtionalized Diels-Alder diene[1][2]. Mukaiyama-Michael-type addition/heterocyclization of trans-1-methoxy-3-trimethylsiloxy-1,3-butadiene (Danishefsky′s diene) with 1,2-diaza-1,3-butadiene has been investigated[3]. Asymmetric hetero-Diels-Alder cyclization of Danishefsky′s diene with benzaldehyde catalyzed by mesoporous inorganic/metalorganic hybrid materials has been reported.

Application

trans-1-Methoxy-3-trimethylsiloxy-1,3-butadiene was used:
  • in the synthesis of sulfone analogues of griseofulvin (sulfogriseofulvins)[4], 4H-1-aminopyrroles[3] and 4,5H-pyrazoles[3]
  • as Diels-Alder diene for the synthesis of pyridones and pyranones
  • as reagent employed in the Mannich-Michael reaction for preparation of piperidinones and enaminones

accessory

Product No.
Description
Pricing

pictograms

Flame
GHS02

signalword

Warning

hcodes

H226

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

138.2 °F - closed cup

flash_point_c

59 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBP3497
SHBK6850
SHBF8895V
SHBF2984V
SHBD4654V

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

The Journal of Organic Chemistry, 57, 3605-3605 (1992)
Tetrahedron, 49, 1749-1749 (1993)
Mingji Dai et al.
Journal of the American Chemical Society, 129(3), 645-657 (2007-01-18)
The paper describes the course of cycloadditions of Diels-Alder dienophiles containing linked enyne sites, each substituted with activating groups. Consistently, it was found that in the enyne cases the Diels-Alder reaction occurred specifically at the acetylenic center. Furthermore, it was
Marie-Laure Teyssot et al.
The Journal of organic chemistry, 72(7), 2364-2373 (2007-03-10)
Electron-poor 6-oxo-1-sulfonyl-1,6-dihydropyridine-3-carboxylates 1b-d undergo cross-Diels-Alder reactions with electron-rich dienes 4a-f under hyperbaric conditions, reacting either as dienophiles to yield normal-electron-demand (NED) cycloadducts 10 and/or 11 or as dienes to give inverse-electron-demand (IED) cycloadducts 12 and/or 13. The latter are converted
M Friedrich et al.
Archiv der Pharmazie, 329(7), 361-370 (1996-07-01)
Syntheses of substituted, especially of fluoro substituted benzoxathiole 1,1-dioxides, are described. These derivatives were transformed via the Peterson olefination into substituted 2-alkylidene derivatives 27. Diels-Alder reactions of 27 with 1,1-dimethoxy- and 1-methoxy-3-trimethylsiloxy-1,3-butadiene (30, 32) gave sulfone analogues 31 of griseofulvin
View All Related Papers

Global Trade Item Number

SKUGTIN
212830-1G04061838772350
212830-5G04061838772367

Questions

Reviews

No rating value

Active Filters

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