Ethyl alpha-Cyanocinnamate TCI C0448

Chemical Identity

Other names: 2-Cyano-3-phenylacrylic Acid Ethyl Ester · alpha-Cyanocinnamic Acid Ethyl Ester · Ethyl 2-Cyano-3-phenylacrylate
CAS No.: 2025-40-3
PubChem: CID 74845·SID 87565569
Formula: C12H11NO2
Molecular weight: 201.23 g/mol
Purity: >98.0%(GC)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: ethyl 2-cyano-3-phenylprop-2-enoate
SMILES: CCOC(=O)C(=CC1=CC=CC=C1)C#N
InChIKey: KCDAMWRCUXGACP-UHFFFAOYSA-N
MDL: MDL00009137

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Dokumen Keamanan & Mutu

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CoA (Certificate of Analysis)

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Ethyl alpha-Cyanocinnamate from TCI is a phenyl-substituted cyanoacrylate ester. Its structure can be viewed as the Knoevenagel condensation product of benzaldehyde and ethyl cyanoacetate. The molecule contains a carbon-carbon double bond with a phenyl ring on one side and both a nitrile group and an ester group on the other. Together these form a strongly electron-poor conjugated system. In the laboratory, the compound serves as a building block and reactive Michael acceptor for building carbon frameworks and heterocyclic rings, which is why it sits among the non-heterocyclic building blocks in organic synthesis.

Chemists choose this compound because the two electron-withdrawing groups on the alpha carbon make its double bond much more electrophilic than that of an ordinary cinnamate ester. Nucleophiles such as thiols, amines, enolates, and active methylene compounds add readily at the beta carbon. The resulting adducts still carry both the nitrile and the ester, so they can be cyclized further into pyridines, pyrans, or other heterocycles. This retained functionality makes the material especially useful in sequential (domino) and multicomponent reactions, where one starting material has to support several bond-forming steps in a single process.

In Indonesia, Ethyl alpha-Cyanocinnamate is relevant to university organic chemistry laboratories, research institutes, and pharmaceutical development groups that work on synthetic methods and heterocyclic chemistry. Research teams studying Knoevenagel catalysts often use it as a reference product to compare how different catalysts perform. Graduate students and researchers designing Michael addition or cyclization sequences also find it a practical, well-defined substrate. AMI Scientific supplies the TCI material to these laboratories as a dependable option for routine synthesis and method development.

Related TCI products

Michael addition studies: the strongly electron-poor double bond lets thiols, amines, enolates, and active methylene compounds add readily at the beta carbon, so the compound works well for exploring conjugate addition reactions.
Heterocycle synthesis: adducts formed from this compound keep both the nitrile and ester groups, which can be cyclized further to build pyridine, pyran, and other heterocyclic ring systems.
Domino and multicomponent reactions: because the compound can take part in several bond-forming steps one after another, it suits cascade sequences that build complex molecules efficiently in one reaction vessel.
Knoevenagel catalyst evaluation: as the condensation product of benzaldehyde and ethyl cyanoacetate, it is often used as a reference product when comparing the activity and selectivity of new catalysts.
Carbon framework construction: as a reactive non-heterocyclic building block, it gives synthetic chemists a conjugated scaffold for assembling larger carbon skeletons in methodology and target-oriented synthesis.

Brand	TCI (product code C0448)
CAS number	2025-40-3
Molecular formula	—
Purity	—
Category	Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack sizes	available in the pack sizes offered by TCI; please contact AMI Scientific to confirm current options
Physical form	refer to the TCI product label and Certificate of Analysis
Storage	follow the storage conditions stated on the TCI label and Safety Data Sheet

Store Ethyl alpha-Cyanocinnamate in its original, tightly closed container in a cool, dry, well-ventilated place, away from direct sunlight, heat sources, and incompatible materials such as strong oxidizers, strong bases, and strong nucleophiles. Reseal the container promptly after each use to limit exposure to moisture and air. Handle the material in a fume hood while wearing suitable gloves, safety glasses, and a laboratory coat, and avoid inhaling dust or vapour and contact with skin or eyes. Always read the TCI Safety Data Sheet before use, and dispose of waste according to local regulations and your institution's chemical waste procedures.

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