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Description
TCI D2082 3,5-Dinitrobenzonitrile is a non-heterocyclic building block, a benzonitrile derivative carrying two nitro groups at positions 3 and 5 of the aromatic ring. The simultaneous presence of three electron-withdrawing groups — one nitrile and two nitro groups — leaves the aromatic ring strongly electron-deficient. In the laboratory, this is precisely the property that is exploited: the compound serves as a substrate in nucleophilic aromatic substitution reactions, as a starting material toward aromatic amino derivatives through controlled reduction, and as an electron-acceptor component in studies of charge-transfer complexes and functional materials.
The properties that make it a preferred choice are its high degree of electron deficiency and its symmetrical substitution pattern. The two nitro groups, positioned symmetrically with respect to the nitrile group, simplify the interpretation of spectroscopic data and limit the possible formation of regioisomers. The nitro groups can be reduced stepwise to amines, opening routes toward diaminobenzonitrile and various fused heterocyclic frameworks, while the nitrile group can be hydrolyzed to the corresponding acid or amide and converted into a tetrazole. Its strong electron-acceptor character further broadens the range of transformations available to the synthetic chemist.
In Indonesian laboratories, this building block is typically used at research and method-development scale rather than in bulk production. It suits university and institutional synthetic chemistry groups preparing substituted aromatic intermediates, materials chemistry laboratories investigating electron-acceptor systems, and R&D units building compound libraries around nitroaromatic and aminoaromatic scaffolds. Because the reactions involved are usually run on a milligram-to-gram scale, the compound is normally ordered in research quantities alongside other non-heterocyclic building blocks.
Laboratory Applications
- Nucleophilic aromatic substitution — the strongly electron-deficient ring readily accepts attack by nucleophiles, making this a dependable model substrate for both mechanistic study and preparative displacement chemistry.
- Controlled reduction to aromatic amines — the two nitro groups can be reduced stepwise, giving access to amino- and diaminobenzonitrile intermediates that would otherwise require lengthier synthetic sequences.
- Synthesis of fused heterocyclic frameworks — the amine products obtained after reduction can be cyclized with the adjacent functionality to construct condensed heterocyclic cores of research interest.
- Nitrile group transformations — the cyano substituent can be hydrolyzed to the corresponding carboxylic acid or amide, or converted into a tetrazole ring for further functional group elaboration.
- Charge-transfer and functional materials studies — its pronounced electron-acceptor character makes it a useful partner in charge-transfer complex investigations and in the preparation of electron-deficient functional materials.
Specifications
- Brand: TCI (Tokyo Chemical Industry)
- CAS number: 4110-35-4
- Catalogue number: D2082
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: research-scale packaging as supplied by the manufacturer; please confirm the available pack size when ordering
- Storage: store in a tightly closed container, in a cool, dry and well-ventilated place
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area, away from heat sources, direct sunlight, and incompatible materials such as strong reducing agents and strong bases. Keep the material in its original manufacturer container, or in a chemically compatible tightly sealed glass container clearly labelled with the compound name and CAS number. Handle in a fume hood, using safety goggles, a laboratory coat, and suitable chemical-resistant gloves, and avoid the generation and inhalation of dust. As with all nitroaromatic compounds, avoid mechanical shock, friction, and unnecessary heating. Always consult the manufacturer's Safety Data Sheet before use, and dispose of residues and contaminated materials through your institution's chemical waste procedures.
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