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Description
TCI D4041 4,5-Dichloro-2-nitroaniline is a non-heterocyclic building block belonging to the aniline derivative family, carrying three functional groups on a single benzene ring: an amino group, a nitro group positioned ortho to the amino group, and two chlorine atoms at the 4 and 5 positions. This particular arrangement of substituents makes the compound a highly productive starting material for the synthesis of fused heterocyclic compounds. In the laboratory, ortho-nitroaniline compounds are classically reduced to ortho-phenylenediamines, which are then condensed further into benzimidazoles, quinoxalines, benzotriazoles, or phenazines, giving the compound a well-established and dependable synthetic pathway.
The property that makes this compound a frequent choice is its neatly ordered electronic profile. The strongly electron-withdrawing nitro group activates the ring toward nucleophilic aromatic substitution, so the chlorine atoms at specific positions can be displaced by nucleophiles such as amines, alkoxides, or thiolates under reasonable conditions. The nitro group itself functions as a masked amine that can be reduced whenever required, giving researchers flexible control over reaction sequence. The two chlorine atoms, meanwhile, contribute additional handles for further functionalization, so a single starting material can be elaborated along several divergent routes without switching to a different precursor.
In Indonesian laboratories, this building block is typically used in organic synthesis and medicinal chemistry research groups at universities and research institutes, as well as in industrial R&D laboratories developing dyes, agrochemical intermediates, and heterocyclic active compounds. Because the reduction–condensation sequence toward benzimidazoles and related fused systems is thoroughly documented, the material fits well into teaching laboratories and graduate research programs where reproducible, literature-supported procedures are important for training and for method development work.
Laboratory Applications
- Benzimidazole synthesis — the ortho-nitroaniline motif is reduced to an ortho-phenylenediamine and then condensed with carboxylic acid derivatives, giving a reliable and well-documented route to substituted benzimidazole cores.
- Quinoxaline and phenazine preparation — the same diamine intermediate condenses readily with dicarbonyl partners, allowing researchers to assemble fused nitrogen heterocycles from a single, conveniently substituted aromatic precursor.
- Nucleophilic aromatic substitution studies — the strongly electron-withdrawing nitro group activates the ring so chlorine atoms can be displaced by amines, alkoxides, or thiolates under reasonable laboratory conditions.
- Medicinal chemistry intermediate work — the three orthogonal functional groups let chemists build diverse analogue libraries around a common scaffold without changing to a different starting material for each series.
- Dye and agrochemical intermediate research — the chlorinated nitroaniline framework serves as a starting point for developing colorants and crop-protection intermediates that rely on fused heterocyclic or aminated aromatic structures.
Specifications
- Brand: TCI (Tokyo Chemical Industry)
- CAS number: 6641-64-1
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Product code: D4041
- Pack sizes: available in standard TCI research-scale packaging; please confirm the required pack size when ordering
- Storage: keep in a tightly closed original container, protected from light, in a cool and well-ventilated area
Handling and Storage
Store the material in its original tightly closed container in a cool, dry, and well-ventilated area, protected from direct sunlight and away from heat sources, strong oxidizing agents, and strong bases. Use chemically compatible containers such as amber glass bottles or the supplier's original packaging, and keep them clearly labelled. Handle inside a fume hood and wear appropriate personal protective equipment, including nitrile gloves, safety goggles, and a laboratory coat, since nitroaromatic and chlorinated aniline compounds can be harmful on skin contact or inhalation. Avoid generating dust when weighing, wash hands thoroughly after handling, and dispose of residues and contaminated materials in accordance with institutional chemical waste procedures. Always consult the manufacturer's Safety Data Sheet before use.
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