Ethoxymethylenemalononitrile

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Cat Number

INT123068

CAS Number

123-06-8

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Product Detail Description Customer Q&A

CAS Number

123-06-8

Storage

Room temperature

Synonyms

(beta-Ethoxymethylene)malononitrile;(b-Ethoxymethylene)malononitrile;(ethoxymethylene)-malononitril;(ethoxymethylene)-propanedinitril;(Ethoxymethylene)propanedinitrile

Molecular Formula

C6H6N2O

Molecular Weight

122.12

Smiles

CCO\C=C(\C#N)C#N

Appearance

Clear colorless to yellow liquid

Melting Point

65℃

Boiling Point

160℃

Relative Density

1.22

General Description

Ethoxymethylenemalononitrile (also known as ethyl (ethoxymethylene)malononitrile) is an activated alkene featuring both an ethoxymethylene group and two nitrile groups. The electron-withdrawing dual nitrile substitution makes the C=C double bond highly electrophilic, susceptible to nucleophilic attack by amines (Knorr-type condensation) and active methylene compounds (Knoevenagel condensation), making it a versatile C-1 building block and cyclization precursor.

Mechanism of Action

Ethoxymethylenemalononitrile acts as an electrophilic C-1 synthon in heterocyclic synthesis. The ethoxymethylene group is an excellent leaving group in condensation reactions with bifunctional nucleophiles such as hydrazines, hydroxylamines, amidines, and guanidines, forming pyrazoles, isoxazoles, pyrimidines, and related heterocycles. The dual nitrile groups contribute both electronic activation and serve as latent functionality for further transformation (hydrolysis to amides or acids).

Application

Ethoxymethylenemalononitrile is used extensively as a versatile intermediate in the synthesis of pharmaceutical heterocycles including pyrimidines, pyrazoles, purines, and other nitrogen-containing heterocyclic systems. It is a key precursor in the synthesis of nucleotide analogs, nucleoside derivatives, and heterocyclic drug scaffolds. It is also employed in the synthesis of dyes, pigments, and organic semiconductors.

What is the recommended storage condition for Ethoxymethylenemalononitrile?

It should be stored at controlled room temperature in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

Can we obtain batch-specific analytical data for Ethoxymethylenemalononitrile?

Batch-specific COA documents are standard with every shipment. Additional analytical reports, including HPLC chromatograms or spectral data, may be provided upon request.

What scale of supply is available for Ethoxymethylenemalononitrile for pilot or commercial synthesis?

Supply is available from laboratory research scale through multi-kilogram pilot quantities. Commercial-scale supply can be discussed based on projected demand.

What functional groups in Ethoxymethylenemalononitrile are available for further chemical modification?

The specific reactive handles present in this intermediate can be confirmed by reviewing the technical data sheet. Our team can provide structural and reactivity information relevant to your synthetic route.

What is the minimum order quantity (MOQ) for Ethoxymethylenemalononitrile?

Flexible MOQ options are available to support both early-stage research and large-scale manufacturing needs. Our team can tailor order quantities to match your specific requirements.