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Description
TCI C2083 4-Cyanoindole is an indole derivative carrying a cyano group at the fourth position of the benzene ring of the indole system. Indole itself is a bicyclic heterocyclic framework of major importance in chemistry, forming the core of numerous natural products, the amino acid tryptophan, and a large number of pharmacologically active molecules. As a heterocyclic building block, this material delivers a complete indole skeleton with a functional group already installed at a position that is difficult to reach through direct substitution reactions, helping researchers save several synthetic steps that are normally complicated and low-yielding.
The property that makes it a preferred choice is the combination of a nucleophilic indole nitrogen and a strongly electron-withdrawing cyano group. The nitrogen of the pyrrole ring can be alkylated, arylated, or protected as required, while the third position of the indole ring remains open for electrophilic substitution reactions such as acylation and formylation. The cyano group at the fourth position exerts a distinctive electronic influence across the whole aromatic system and can at the same time be converted into a carboxylic acid, an amide, an aldehyde, an amine, or a tetrazole ring. This flexibility allows a single starting material to serve many different synthetic routes.
In Indonesian laboratories, this building block is typically used in university research groups, pharmaceutical research and development units, and institutional chemistry laboratories that work on the synthesis of heterocyclic compounds. It is generally handled at small research scale, weighed out for multi-step synthesis routes, and consumed gradually across a series of reactions. Because it shortens routes that would otherwise require difficult regioselective functionalisation, it suits laboratories where reagent supply and instrument time are planned carefully.
Laboratory Applications
- Medicinal chemistry synthesis: the indole core is present in many pharmacologically active molecules, and the pre-installed cyano group allows rapid preparation of analogue series without lengthy regioselective functionalisation of the benzene ring.
- Preparation of carboxylic acids and amides: the cyano group can be hydrolysed or partially converted, giving direct access to 4-substituted indole acids and amides used as intermediates in further coupling chemistry.
- Tetrazole synthesis: the nitrile function serves as a convenient precursor to a tetrazole ring, a group frequently employed by researchers as a bioisosteric replacement in molecular design work.
- Amine and aldehyde intermediates: controlled reduction of the cyano group provides aminomethyl or aldehyde derivatives, opening routes to reductive amination, condensation, and other standard downstream laboratory transformations.
- Functionalisation at nitrogen and position three: the free indole nitrogen accepts alkylation, arylation, or protection while position three remains available for acylation and formylation, supporting diverse scaffold elaboration.
Specifications
- Brand: TCI
- CAS number: 16136-52-0
- Chemical name: 4-Cyanoindole
- Catalogue reference: C2083
- Category: Chemistry > Building Blocks > Heterocyclic Building Blocks
- Pack sizes: available in the research-scale pack sizes offered for this catalogue item; please confirm the current option when ordering
- Storage: store according to the conditions stated on the manufacturer label and the accompanying safety data sheet
Handling and Storage
Store the container tightly closed in a cool, dry, and well-ventilated place, away from direct sunlight, heat sources, moisture, and incompatible chemicals, following the conditions stated on the manufacturer label and safety data sheet. Keep the material in its original container or in a clean, properly labelled glass container that is chemically resistant and sealed to limit exposure to air and humidity. Handle the substance in a fume hood, wearing a laboratory coat, safety goggles, and suitable chemical-resistant gloves. Weigh out only the quantity needed, avoid generating dust, and close the container immediately after use. Do not eat, drink, or store food in the working area, and wash hands thoroughly after handling. Dispose of residues and contaminated materials in accordance with institutional chemical waste procedures and applicable local regulations.
