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    55107-14-7

    Catalog No. EBD4104

    CAS 55107-14-7

    Name Methyl pivaloylacetate

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    Basic Information

    Synonyms: Pivaloylaceticacidmethylester Methyl4,4-dimethyl-3-oxopentanoate Methylpivaloylacetate Methyl4,4-Dimethyl-3-oxovalerate 4,4-Dimethyl-3-oxo-pentanoicacidmethylester pentanoicacid,4,4-dimethyl-3-oxo-,methylester

    Molecular Formula: C8H14O3

    Molecular Weight: 158.19

    MDL Number: MFCD00008847

    Categories: Synthetic Chemistry > Basic Synthetic Reagents > C-C Bond Formation Reagents

    Product Description:
    Methyl pivaloylacetate, also known as methyl 4,4-dimethyl-3-oxopentanoate, is a versatile β-keto ester characterized by a pivaloyl (tert-butyl carbonyl) group. It is a colorless to pale yellow liquid with a molecular formula of C8H14O3. This compound is a key building block in organic synthesis due to its active methylene group flanked by two carbonyl functionalities. Its primary application is as a precursor in the synthesis of various heterocyclic compounds, particularly pyrazoles and pyrimidines. The active methylene group readily undergoes condensation reactions with hydrazines, amidines, and other bifunctional nucleophiles to construct these important heterocyclic cores. It is also employed in Claisen condensation and Michael addition reactions to form more complex molecular structures. These synthetic pathways are fundamental in medicinal and agrochemical research for creating active ingredients. As a specialized synthon, it is less common than simpler β-keto esters like ethyl acetoacetate but offers the advantage of the sterically hindered tert-butyl group, which can influence the regioselectivity and stability of the resulting products. It is typically handled under standard laboratory conditions, requiring protection from moisture.
    Physical Properties

    Boiling Point: 67-70 °C/13 mmHg(lit.)

    Flash Point: 77 °C

    Density: 0.99 g/mL at 25 °C(lit.)

    Refractivity: n20/D 1.487(lit.)

    Analytical Data

    Appearance: Clear colorless to orange liquid

    mg g kg ml l t