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Description
TCI C2247 2-Cyanophenylacetonitrile is an aromatic dinitrile compound that places one nitrile group directly on the benzene ring while a second acetonitrile group occupies the adjacent ortho position. This arrangement of two neighbouring cyano groups is precisely what makes the material such a high-value building block for synthetic chemists, because the distance between the two functionalities is ideal for intramolecular cyclisation reactions that construct bicyclic frameworks. In organic laboratories, the compound serves as a starting point for preparing isoquinoline, isoindole and aminonaphthalene derivatives, along with a range of other nitrogen-containing heterocyclic skeletons that are difficult to assemble from simpler starting materials.
The property that drives its selection is the acidity of the methylene protons situated between the aromatic ring and the nitrile group. These protons are released relatively easily by a moderate base, generating a stabilised carbanion that is immediately ready to react with aldehydes, ketones, alkyl halides and other electrophiles through Knoevenagel condensation and alkylation. Once the carbanion has formed, the aromatic nitrile group at the ortho position sits exactly within reach of intramolecular attack, so ring closure frequently proceeds within a single reaction vessel. The solid form is stable under ordinary storage conditions, which supports reliable handling and reproducible weighing.
Within Indonesian laboratories, this reagent is typically found in synthetic organic chemistry groups at universities and research institutes, as well as in pharmaceutical and fine-chemical development work where heterocyclic scaffolds are needed. It is most often used at bench scale for methodology studies, thesis research and route exploration toward nitrogen heterocycles, where a dependable dinitrile building block from an established brand shortens the path from commercial starting material to the target skeleton.
Laboratory Applications
Isoquinoline synthesis — the ortho-positioned aromatic nitrile and the acidic methylene centre allow the two-ring nitrogen framework to be closed efficiently from a single precursor.
Isoindole derivative preparation — carbanion formation followed by intramolecular attack on the adjacent cyano group builds the fused five-membered nitrogen ring in one operation.
Aminonaphthalene route development — the dinitrile arrangement provides both the carbon skeleton and the nitrogen source needed to reach amino-substituted fused aromatic products.
Knoevenagel condensation studies — the readily deprotonated methylene position couples with aldehydes and ketones, making this a convenient substrate for condensation methodology work.
Alkylation and carbanion chemistry — moderate bases generate a stabilised carbanion that reacts cleanly with alkyl halides and other electrophiles for side-chain elaboration.
Specifications
Brand: TCI
CAS number: 3759-28-2
Product code: C2247
Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack sizes: available in standard TCI catalogue pack sizes; please confirm the required size when ordering
Physical form: solid, stable under ordinary storage conditions
Handling and Storage
Store the material in its original tightly closed container, kept in a cool, dry and well-ventilated area away from direct sunlight, moisture and incompatible substances. The solid form is stable under ordinary storage conditions, but containers should be resealed promptly after each use to limit exposure to atmospheric moisture. Handle the compound in a fume hood using standard personal protective equipment, including safety glasses, chemical-resistant gloves and a laboratory coat. Avoid generating dust during weighing and transfer, use clean dry spatulas to prevent contamination of the bulk material, and consult the manufacturer's safety data sheet before first use.
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