1-Methoxy-3-trimethylsiloxy-1,3-butadiene
Synonym(s):Danishefsky’s diene
- CAS NO.：54125-02-9
- Empirical Formula: C8H16O2Si
- Molecular Weight: 172.3
- MDL number: MFCD00008498
- EINECS: 629-035-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2026-09-12 18:50:23
What is 1-Methoxy-3-trimethylsiloxy-1,3-butadiene?
The Uses of 1-Methoxy-3-trimethylsiloxy-1,3-butadiene
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.]
Properties of 1-Methoxy-3-trimethylsiloxy-1,3-butadiene
| Boiling point: | 68-69 °C/14 mmHg (lit.) |
| Density | 0.885 g/mL at 25 °C (lit.) |
| refractive index | n |
| Flash point: | 113 °F |
| storage temp. | 2-8°C |
| Specific Gravity | 0.89 |
| Water Solubility | Miscible with most organic solvents. Immiscible with water. |
| Sensitive | Moisture Sensitive |
| Hydrolytic Sensitivity | 8: reacts rapidly with moisture, water, protic solvents |
| Merck | 14,6001 |
| BRN | 1616761 |
| CAS DataBase Reference | 54125-02-9(CAS DataBase Reference) |
Safety information for 1-Methoxy-3-trimethylsiloxy-1,3-butadiene
| Signal word | Warning |
| Pictogram(s) |
 Flame Flammables GHS02 |
| GHS Hazard Statements |
H226:Flammable liquids |
| Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P233:Keep container tightly closed. P240:Ground/bond container and receiving equipment. P241:Use explosion-proof electrical/ventilating/lighting/…/equipment. P242:Use only non-sparking tools. P243:Take precautionary measures against static discharge. |
Computed Descriptors for 1-Methoxy-3-trimethylsiloxy-1,3-butadiene
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