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    31469-15-5

    Catalog No. EBD54866

    CAS 31469-15-5

    Name 1-Methoxy-2-methyl-1-(trimethylsiloxy)propene

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    Basic Information

    Synonyms: 1-Methoxy-2-methyl-1-(trimethylsiloxy)propene

    Molecular Formula: C8H18O2Si

    Molecular Weight: 174.31

    MDL Number: MFCD00010232

    Categories: Synthetic Chemistry > Organic Building Blocks > Other Organic Building Blocks Synthetic Chemistry > Organometallic Reagents > Organosilicon Reagents

    Product Description:
    1-Methoxy-2-methyl-1-(trimethylsiloxy)propene, also known as the Danishefsky-Kitahara diene, is a highly versatile and reactive silyl enol ether derivative. Its chemical structure features a conjugated diene system with a methoxy group and a trimethylsiloxy group, making it a powerful electron-rich diene for cycloaddition reactions. This compound is a cornerstone reagent in organic synthesis, primarily used as a diene in hetero-Diels-Alder reactions. It reacts efficiently with a wide range of dienophiles, particularly aldehydes and ketones, to form dihydropyranone derivatives. These products serve as key intermediates in the total synthesis of numerous complex natural products, including carbohydrates, macrolides, and various pharmaceuticals. Its reactivity profile allows for the stereoselective construction of oxygen-containing heterocycles. Due to its moisture sensitivity, it must be handled under inert atmosphere conditions. Its primary role is as a specialized building block in academic and industrial research for constructing complex molecular architectures, rather than having a direct, standalone application in materials or pharmaceuticals.
    Physical Properties

    Boiling Point: 35 °C/15 mmHg(lit.)

    Flash Point: 30 °C

    Density: 0.858 g/mL at 25 °C(lit.)

    Refractivity: n20/D 1.415(lit.)

    Storage: 2-8°C

    Safety Information

    Packing Level: III

    Hazard Category: 3

    Transport Codes: 3271

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