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Description
TCI D2701 2,4-Dinitrobromobenzene is a synthesis chemical supplied by TCI and classified within the non-heterocyclic building blocks group. The compound consists of a benzene ring bearing a bromine atom that acts as the leaving group, together with two nitro groups at the 2 and 4 positions that activate the ring. This arrangement makes it a textbook example of a nucleophilic aromatic substitution substrate in organic chemistry. In the laboratory, the material serves as a labelling reagent for nucleophilic groups, as an aromatic electrophile for constructing carbon–nitrogen, carbon–oxygen, and carbon–sulfur bonds, and as an important teaching material in reaction mechanism practicals.
Its principal characteristic is the strong activation provided by the two nitro groups, which sit ortho and para to the bromine atom. This arrangement stabilises the negatively charged intermediate formed when a nucleophile attacks the ring, so the bromine atom is readily displaced without requiring a metal catalyst or elevated temperature. For this reason, the compound reacts smoothly with primary and secondary amines, phenolates, alkoxides, and thiols. The dinitrophenyl group formed in the resulting product shows a characteristic ultraviolet absorption and tends to crystallise easily — two properties that are very helpful during purification and detection steps.
In Indonesian laboratories, this reagent fits naturally into organic synthesis and analytical work where a reliable aromatic electrophile is needed. Academic and research groups use it to demonstrate nucleophilic aromatic substitution under straightforward conditions, while synthesis laboratories apply it to prepare dinitrophenyl derivatives whose ultraviolet absorption and crystallinity simplify isolation and identification. Because the reaction proceeds without specialised catalysts or high-temperature equipment, it suits both teaching practicals and routine bench-scale preparation.
Laboratory Applications
- Nucleophilic aromatic substitution studies — the two activating nitro groups ortho and para to bromine make displacement proceed reliably, giving a clean model reaction for mechanism investigation.
- Labelling of nucleophilic groups — the reagent attaches a dinitrophenyl group that carries a characteristic ultraviolet absorption, allowing straightforward detection of the labelled product afterwards.
- Carbon–nitrogen bond construction — reacts smoothly with primary and secondary amines to form dinitrophenyl amine derivatives without any need for metal catalysts or forcing conditions.
- Carbon–oxygen bond construction — phenolates and alkoxides displace the bromine atom readily, providing aryl ether products that generally crystallise well for easier purification.
- Teaching practicals on reaction mechanisms — serves as a standard classroom substrate because the activation pattern and the reaction outcome illustrate substitution theory in a clear, reproducible way.
Specifications
- Brand: TCI (Tokyo Chemical Industry)
- CAS number: 584-48-5
- Catalogue number: D2701
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: available in standard TCI catalogue pack sizes; please confirm the required packaging when ordering
- Storage: keep in the closed original container under the storage conditions stated on the manufacturer's label
Handling and Storage
Store the material in its original tightly closed container, kept in a cool, dry, and well-ventilated chemical store away from heat sources, direct sunlight, and incompatible substances — particularly strong bases and reducing agents, given the reactivity of the activated aromatic ring. Use only chemically compatible containers and keep them clearly labelled. All handling, weighing, and transfer operations should be carried out in a fume hood, using appropriate gloves, safety glasses, and a laboratory coat, since dinitroaromatic compounds can irritate skin, eyes, and the respiratory tract. Avoid dust formation and skin contact, wash hands after handling, and collect residues and contaminated consumables as chemical waste for disposal according to institutional procedures. Always consult the manufacturer's Safety Data Sheet before use.
