Name: China Chemical Manufacturer Supply High Quality 2-Chloro-5-nitrobenzaldehyde CAS 6361-21-3
Brand: Wuhan Fortuna Chemical Co., Ltd.

2-Chloro-5-nitrobenzaldehyde is an important organic synthesis intermediate.

1. Basic Chemical Information

Molecular Weight: Approx. 185.56 g/mol

CAS Number: 6361-21-3

Appearance: Typically a white or pale yellow crystalline powder.

Physical Properties:

Melting Point: Approx. 75–77°C

Boiling Point: Approx. 290.3°C

Density: Approx. 1.485 g/cm³

Structural Features: It is a derivative of benzaldehyde with a chlorine atom at the 2-position and a nitro group at the 5-position of the benzene ring. The presence of the nitro group (a strong electron-withdrawing group) and the chlorine atom imparts high reactivity, particularly in nucleophilic substitution reactions.

2. Main Uses

2-Chloro-5-nitrobenzaldehyde serves primarily as an organic synthesis intermediate widely used in the pharmaceutical, agrochemical, and material science industries:

Pharmaceutical Synthesis:

It is a key precursor for synthesizing various drug molecules. Due to the electronic effects of the nitro and chloro groups, it frequently participates in constructing heterocyclic compounds.

For instance, it is used to synthesize benzimidazole derivatives. It can react with nitrogen-containing compounds to form bioactive benzimidazoles, which often exhibit antiparasitic, antibacterial, or antitumor activities.

It is also employed in the synthesis of other nitrogen-containing heterocyclic scaffolds like quinolines and isoquinolines.

Agrochemical Synthesis:

It acts as an intermediate in the manufacture of herbicides, fungicides, and insecticides. The introduction of nitro and chloro groups often enhances the biological activity of the final molecule.

Fine Chemicals and Materials:

Used in the synthesis of specific dyes, pigments, or functional materials.

It can serve as a ligand or precursor for preparing Metal-Organic Frameworks (MOFs) or other functional polymers.

Specific Reaction Examples:

Condensation Reactions: The aldehyde group (-CHO) can participate in Knoevenagel condensations, Wittig reactions, etc., to generate olefinic derivatives (e.g., styrene-type compounds).

Nucleophilic Substitution: Although the chlorine is at the 2-position, influenced by the electron-withdrawing effect of the 5-nitro group, it can be displaced by nucleophiles like amines or alkoxides under specific conditions, introducing new functional groups.

Reduction Reactions: The nitro group can be reduced to an amino group, yielding 2-chloro-5-aminobenzaldehyde, another valuable synthetic building block.

3. Safety and Storage

Stability: Stable under normal temperature and pressure but should be kept away from strong oxidizing agents and strong acids.

Storage Conditions: Must be stored in a sealed container in a cool, dry, and dark place. Some suppliers recommend storage under nitrogen to prevent degradation.

Safety: As a nitro compound and halogenated hydrocarbon, it may possess certain toxicity or irritancy. Appropriate personal protective equipment (gloves, goggles, etc.) should be worn during handling, and operations should be conducted in a fume hood.

In summary, 2-Chloro-5-nitrobenzaldehyde is a versatile chemical building block. Its core value lies in the multiple reactive sites provided by its aldehyde group, chlorine atom, and nitro group, making it an indispensable raw material in the pharmaceutical and fine chemical industries.