MilliporeSigma
All Photos(1)

212830

Sigma-Aldrich

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

95%

Synonym(s):
Danishefsky’s diene
Linear Formula:
(CH3)3SiOC(=CH2)CH=CHOCH3
CAS Number:
Molecular Weight:
172.30
Beilstein:
1616761
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.)

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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[4].

Application

trans-1-Methoxy-3-trimethylsiloxy-1,3-butadiene was used:
  • in the synthesis of sulfone analogues of griseofulvin (sulfogriseofulvins)[5], 4H-1-aminopyrroles[3] and 4,5H-pyrazoles[3]
  • as Diels-Alder diene for the synthesis of pyridones[6] and pyranones[7]
  • as reagent employed in the Mannich-Michael reaction for preparation of piperidinones[8] and enaminones[9]

Packaging

1, 5 g in ampule

Pictograms

Flame

Signal Word

Warning

Hazard Statements

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

138.2 °F - closed cup

Flash Point(C)

59 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

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