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HomeProduct name list1-METHOXY-3-TRIMETHYLSILOXY-1,3-BUTADIENE

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: 2023-04-23 13:52:06
1-METHOXY-3-TRIMETHYLSILOXY-1,3-BUTADIENE Structural

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  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.
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)
ghs
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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