Ethyl 4-(2- Phthalimidoethoxy) acetoacetate(PHEEMA)

Product Description

Ethyl 42Phthalimidoethoxyacetoacetate abbreviated as PHEEMA is a chemical compound that incorporates a phthalimido group and an acetoacetate ester functional group It is typically used in organic synthesis and medicinal chemistry potentially in the development of novel bioactive compounds or as a reagent in chemical transformations

 Chemical Details

 IUPAC Name Ethyl 42Phthalimidoethoxyacetoacetate  

 Molecular Formula C14H15NO4  

 Molecular Weight 26128 gmol  

 Structure

   The molecule contains an ethyl ester group at the acetoacetate position which is a keto ester and a phthalimidoethoxy group at the 4position of the acetoacetate ester

 Physical Properties

 Appearance White to offwhite crystalline solid or powder

 Melting Point Typically between 100120C though it can vary based on purity

 Boiling Point Not readily available but would be high due to the ester and phthalimide groups

 Solubility Soluble in common organic solvents like ethanol acetone and chloroform but likely poorly soluble in water due to the hydrophobic nature of the phthalimide and ethoxy groups

 Density 128 gcm

 Applications

1 Organic Synthesis

    Building Block for Drug Synthesis PHEEMA can serve as an intermediate in the synthesis of phthalimide derivatives and other biologically active molecules

    Key Reagent for Reactions It can participate in nucleophilic substitution reactions where the phthalimido group can be modified and in esterification reactions to form novel derivatives with potential applications in medicinal chemistry

2 Medicinal Chemistry

    Phthalimide Derivatives Phthalimide derivatives are known for their potential neuroactive anticonvulsant and antitumor activities The functionalization of acetoacetate with a phthalimido group might result in compounds with useful biological properties

    Prodrugs PHEEMA could be explored as a prodrug or a precursor to compounds that exhibit enhanced bioavailability or specific pharmacological properties

3 Biological Research

    The ethoxy group in combination with the phthalimido group could influence the compounds ability to cross cellular membranes making it a candidate for cellular penetration studies or drug delivery systems

4 Potential Applications in Agrochemicals

    Similar to other phthalimide derivatives PHEEMA could be evaluated as a pesticide or fungicide precursor due to its ability to interact with biological systems though its primary use is more likely in medicinal chemistry

 Chemical Reactivity

1 Nucleophilic Substitution

    The ethoxy group in the structure might undergo nucleophilic substitution reactions with various nucleophiles allowing for the synthesis of other derivatives or functionalized compounds

2 Enolization Acetoacetate Group

    The acetoacetate group is reactive in enolization reactions where it forms an enolate ion making it useful in Michael addition reactions aldol condensations or Knoevenagel condensations to form carboncarbon bonds

3 Reduction Reactions

    The ester group can be reduced to a hydroxyester which could potentially lead to the formation of alcoholcontaining compounds useful in further synthetic steps

 Synthesis of Ethyl 42Phthalimidoethoxyacetoacetate PHEEMA

1 Step 1  Synthesis of 2Phthalimidoethanol

    A phthalic anhydride or phthalimide can react with ethanolamine or ethanol to form the phthalimidoethoxy group resulting in the intermediate 2phthalimidoethanol

2 Step 2  Esterification

    The 2phthalimidoethanol is then esterified with ethyl acetoacetate using a base like pyridine or sodium ethoxide to form PHEEMA

 Safety and Handling

 Toxicity  

    PHEEMA and similar phthalimide derivatives should be handled with care The phthalimide group can be toxic and may irritate the skin eyes or respiratory system upon exposure

 Precautions  

    Wear appropriate personal protective equipment PPE such as gloves goggles and work under a fume hood to avoid inhalation or contact with the skin

 Storage  

    Store in a cool dry place in tightly sealed containers away from heat and moisture to maintain stability

 Conclusion

Ethyl 42Phthalimidoethoxyacetoacetate PHEEMA is a versatile compound with potential applications in medicinal chemistry particularly as a precursor to phthalimide derivatives and other bioactive molecules Its structure combining a phthalimido group with an acetoacetate ester makes it a useful building block for organic synthesis with possible therapeutic implications such as anticonvulsant or antitumor activity

Would you like additional information on its derivatives specific synthetic methods or potential applications in drug development