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Description
TCI C3074 2-Chloro-6-nitrophenol is a substituted phenol carrying a chlorine substituent and a nitro group positioned ortho to the hydroxyl group. As a non-heterocyclic building block, this compound delivers three distinct functional groups within a single small molecule: a phenolic hydroxyl, a nitro group, and an aromatic halogen. This combination makes it a highly useful starting material in organic synthesis laboratories, particularly for constructing fused heterocyclic compounds such as benzoxazoles, phenoxazines, and aminophenol derivatives that are widely applied in dye research and medicinal chemistry.
The property that leads researchers to select this compound is the diversity of transformations available at each of its functional groups. The nitro group can be reduced to an amine, opening a route toward o-aminophenol, a classic precursor to a range of nitrogen- and oxygen-containing heterocycles. The phenolic hydroxyl group is acidic and therefore easily deprotonated and subsequently alkylated or acylated, while also acting as a nucleophile during ring formation. Meanwhile, the strongly electron-withdrawing nitro group activates the aromatic ring toward nucleophilic aromatic substitution, so that the adjacent chlorine atom becomes a workable leaving group for further substitution chemistry.
In Indonesian laboratories, this material is typically used in university research groups and institutional synthesis facilities working on organic building blocks, dye intermediates, and medicinal chemistry projects. It is drawn upon during multi-step route development, method optimisation, and thesis or postgraduate research where a compact, multifunctional aromatic scaffold is required. Analytical and quality control laboratories may also use it as a reference substrate when developing separation or identification methods for substituted nitrophenols.
Laboratory Applications
- Benzoxazole synthesis: the compound provides both the phenolic oxygen and, after nitro reduction, the amine nitrogen needed to close the fused oxazole ring in a single scaffold.
- Phenoxazine preparation: the activated chlorine and phenolic hydroxyl allow sequential substitution and ring closure, giving access to phenoxazine cores of interest in dye research.
- o-Aminophenol precursor chemistry: reduction of the nitro group yields an aminophenol intermediate that serves as a classic entry point to nitrogen- and oxygen-containing heterocycles.
- Nucleophilic aromatic substitution studies: the strongly electron-withdrawing nitro group activates the ring so the neighbouring chlorine can be displaced by a variety of nucleophiles.
- Phenol derivatisation work: the acidic hydroxyl group is readily deprotonated and then alkylated or acylated, letting chemists build ethers and esters on a multifunctional aromatic platform.
Specifications
- Brand: TCI
- CAS number: 603-86-1
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Product code: C3074
- Pack sizes: available in the standard TCI catalogue pack sizes for this product code
- Storage: store according to the conditions stated on the manufacturer's label and safety data sheet
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area away from direct sunlight, heat sources, and incompatible materials, following the conditions given on the manufacturer's label and safety data sheet. Keep the material in its original supplier container or in a chemically compatible, clearly labelled vessel, and reseal it promptly after each use to limit moisture uptake and contamination. Handle in a fume hood using safety goggles, gloves, and a laboratory coat, avoiding contact with skin and eyes and inhalation of dust. Dispose of residues and contaminated materials in accordance with institutional chemical waste procedures.
