3-Chloro-2-nitrobenzonitrile: Handling, Safety & Lab Use Guide

3-Chloro-2-nitrobenzonitrile is a multifunctional aromatic building block featuring three orthogonally reactive substituents—a cyano group, a nitro group, and a chloro group—that make it a versatile intermediate in pharmaceutical and fine-chemical synthesis.

CAS Number

6575-12-8

Molecular Formula

C₇H₃ClN₂O₂

Molecular Weight

182.56 g/mol

Appearance

Pale yellow to off-white crystalline solid

Storage Condition

Cool, dry, well-ventilated area; away from light and moisture

Key Functional Groups

Nitrile (–CN), Nitro (–NO₂), Chloro (–Cl) on a benzene ring

Chemical Identity and Physical Properties

3-Chloro-2-nitrobenzonitrile (SKU: C192883) is an aromatic organic compound bearing three electron-withdrawing substituents on the benzene ring: a nitrile (–CN) group at position 1, a nitro (–NO₂) group at position 2, and a chloro (–Cl) group at position 3. The combined electron-withdrawing effect of these substituents renders the aromatic ring highly electron-deficient, significantly activating the ring toward nucleophilic aromatic substitution (SNAr) reactions, particularly at the carbon bearing the chloro leaving group.

The compound presents as a pale yellow to off-white crystalline solid at room temperature. Its molecular formula is C₇H₃ClN₂O₂ with a molecular weight of 182.56 g/mol. The strong electron-withdrawing character of the nitrile and nitro groups lowers the electron density of the ring, influencing both reactivity and spectroscopic properties. Researchers should verify melting point and purity specifications on the Certificate of Analysis (CoA) supplied with each lot from Aladdin Scientific.

Synthetic Applications and Reactivity

The three reactive handles present in 3-Chloro-2-nitrobenzonitrile make it a valuable building block in synthetic chemistry. The key modes of reactivity include:

• Nucleophilic Aromatic Substitution (SNAr): The chloro group, activated by the flanking nitro and cyano groups, undergoes facile SNAr with amines, alkoxides, and thiolates. This allows direct construction of diaryl ethers, thioethers, and secondary or tertiary aniline derivatives under mild conditions.
• Nitrile Transformations: The –CN group can be hydrolyzed to a carboxylic acid or amide, reduced to an amine, or used in cycloaddition chemistry, providing routes to heterocyclic scaffolds such as tetrazoles and oxazoles.
• Nitro Group Reduction: Reduction of the –NO₂ group (e.g., with Fe/AcOH, catalytic hydrogenation, or SnCl₂) affords the corresponding 2-aminobenzonitrile derivative, a precursor to benzimidazoles, anthranils, and related heterocycles of pharmaceutical interest.
• Cross-Coupling Chemistry: Under appropriate palladium-catalyzed conditions, the aryl chloride can participate in Suzuki–Miyaura or Buchwald–Hartwig coupling reactions, though the electron-deficient ring may require optimization of catalyst and ligand systems.

These converging reaction pathways position 3-Chloro-2-nitrobenzonitrile as a strategic intermediate for medicinal chemists preparing diverse compound libraries.

Safe Handling and Hazard Information

3-Chloro-2-nitrobenzonitrile should be treated as a potentially harmful chemical. Researchers must consult the current Safety Data Sheet (SDS) before use. General precautionary measures include:

• Personal Protective Equipment (PPE): Wear appropriate chemical-resistant gloves (e.g., nitrile), lab coat, and safety goggles. Use a dust mask or respiratory protection when handling the powder to avoid inhalation of fine particles.
• Engineering Controls: Handle in a well-ventilated fume hood to minimize inhalation exposure to dust or vapors.
• Skin and Eye Contact: Avoid direct contact. In case of skin contact, wash thoroughly with soap and water. For eye contact, immediately rinse with copious water for at least 15 minutes and seek medical attention.
• Ingestion/Inhalation: Do not eat, drink, or smoke when handling the compound. If inhaled, move to fresh air immediately and seek medical advice if symptoms persist.
• Nitro Compound Considerations: Nitro-aromatic compounds may present mild oxidizing character. Avoid contact with strong reducing agents, open flames, or sources of ignition.

Note: Specific GHS hazard classifications, hazard statements (H-codes), and precautionary statements (P-codes) must be confirmed from the official Aladdin Scientific SDS for lot C192883. The information above is general guidance only.

Storage, Stability and Disposal

Storage: Store 3-Chloro-2-nitrobenzonitrile in a tightly sealed container in a cool (typically 2–25 °C, confirm on CoA), dry, and well-ventilated area, protected from direct light and moisture. Keep away from incompatible materials including strong oxidizers, strong bases, and strong reducing agents. Segregate from food and feedstuffs.

Stability: The compound is expected to be stable under recommended storage conditions for the shelf life stated on the product label. The nitrile and nitro functional groups are stable at ambient temperatures but may react under strongly acidic, basic, or reducing conditions. Monitor stored material for any color change or clumping that may indicate decomposition or moisture uptake.

Disposal: Dispose of the compound and contaminated materials in accordance with local, regional, and national environmental regulations. Do not pour down the drain or into the environment. Incineration by a licensed waste-disposal contractor is the typically recommended route for halogenated aromatic compounds. Consult your institution's Environmental Health and Safety (EHS) office for site-specific disposal protocols.

Quality Specifications and Ordering Information

Aladdin Scientific supplies 3-Chloro-2-nitrobenzonitrile under SKU C192883. Each shipment is accompanied by a Certificate of Analysis (CoA) documenting lot-specific purity, appearance, and characterization data. Researchers are encouraged to:

• Verify purity by the method stated on the CoA (typically HPLC or GC) to confirm suitability for their application.
• Request the Safety Data Sheet (SDS) prior to use for full hazard, first-aid, and handling information.
• Contact Aladdin Scientific technical support for guidance on custom quantities, bulk pricing, or purity grades beyond the standard catalog offering.

For procurement teams, the compound can be ordered directly through the Aladdin Scientific online catalog. Reference SKU C192883 when placing orders to ensure correct product identification. Expedited shipping options and institutional purchase order workflows are available; consult the Aladdin payment, pricing, and promotions policy for current terms.

Frequently asked questions

What makes 3-Chloro-2-nitrobenzonitrile reactive toward nucleophilic aromatic substitution?

The chloro group at position 3 is flanked by a nitro group (ortho) and a cyano group (ipso relative to CN), both of which are strongly electron-withdrawing. This electron deficiency stabilizes the Meisenheimer complex intermediate formed during SNAr, lowering the activation energy and making the displacement of chloride feasible under mild conditions with nitrogen, oxygen, or sulfur nucleophiles.

How should I handle 3-Chloro-2-nitrobenzonitrile safely in the laboratory?

Always work in a well-ventilated fume hood wearing nitrile gloves, a lab coat, and safety goggles. Avoid generating or inhaling dust when weighing the solid. Consult the current SDS provided by Aladdin Scientific (SKU C192883) for specific GHS hazard classifications, H-codes, and P-codes before beginning any experimental work.

What are the recommended storage conditions for C192883?

Store the compound in a tightly closed container in a cool, dry, and well-ventilated location, protected from light and moisture. Keep away from strong oxidizers, reducing agents, and bases. Always confirm the precise temperature range and shelf life from the lot-specific Certificate of Analysis included with your shipment.

Can 3-Chloro-2-nitrobenzonitrile be used in palladium-catalyzed cross-coupling reactions?

Yes, the aryl chloride moiety can in principle participate in Suzuki–Miyaura, Negishi, or Buchwald–Hartwig coupling reactions. However, the strongly electron-deficient ring may necessitate optimization of the palladium source, phosphine ligand, base, and solvent system to achieve satisfactory yields. Pilot screening experiments are recommended before scale-up.

How do I request a Certificate of Analysis or Safety Data Sheet for C192883?

Certificates of Analysis and Safety Data Sheets for SKU C192883 can be obtained through the Aladdin Scientific website by searching the SKU, or by contacting Aladdin Scientific customer service directly. Always use the document corresponding to your specific lot number to ensure accuracy.

References

1. Aladdin Scientific Product Page: 3-Chloro-2-nitrobenzonitrile, SKU C192883. Aladdin Scientific Co., Ltd.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 4th ed. Wiley-Interscience, 1992. (Nucleophilic Aromatic Substitution chapter)
3. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry. 2nd ed. Oxford University Press, 2012. (Aromatic chemistry and functional group interconversions)
4. Globally Harmonized System of Classification and Labelling of Chemicals (GHS), 9th revised edition. United Nations, 2021.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.