1-METHOXY-3-TRIMETHYLSILOXY-1,3-BUTADIENE Property

Boiling point:

68-69 °C/14 mmHg (lit.)

Density 

0.885 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.454(lit.)

Flash point:

113 °F

storage temp. 

2-8°C

Specific Gravity

0.89

Water Solubility 

Miscible with most organic solvents. Immiscible with water.

Hydrolytic Sensitivity

8: reacts rapidly with moisture, water, protic solvents

Sensitive 

Moisture Sensitive

Merck 

14,6001

BRN 

1616761

CAS DataBase Reference

54125-02-9(CAS DataBase Reference)

Safety

Risk Statements 

10

Safety Statements 

23-24/25

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

F 

10-21

TSCA 

No

HazardClass 

3

PackingGroup 

III

HS Code 

2931900090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H226Flammable liquid and vapour

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

1-METHOXY-3-TRIMETHYLSILOXY-1,3-BUTADIENE Chemical Properties,Usage,Production

Uses

1-Methoxy-3-trimethylsiloxy-1,3-butadiene is employed as a reagent in Mannich-Michael reaction for the synthesis of piperidinones and enaminones. As Diels-Alder diene, it is used in the synthesis of pyridones and pyranones, sulfone analogues of griseofulvin (sulfogriseofulvins) and 4H-1-aminopyrroles and 4, 5H-pyrazoles.

General Description

trans-1-methoxy-3-trimethylsiloxy-1,3-butadiene is a funtionalized Diels-Alder diene. 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. Asymmetric hetero-Diels-Alder cyclization of Danishefsky′s diene with benzaldehyde catalyzed by mesoporous inorganic/metalorganic hybrid materials has been reported.

Purification Methods

It may contain up to 1% of the precursor 4-methoxybut-4-ene-2-one. It is easily purified by distilling through a Vigreux column (p 11) in a vacuum and taking the middle fraction. [Danishefsky & Kitihara J Am Chem Soc 96 7807 1974, Danishefsky Acc Chem Res 14 400 1981.]