Chloronitromethane: Properties, Safety & Lab Applications

Chloronitromethane is a halogenated nitroalkane reagent of growing interest in synthetic organic chemistry due to its dual electrophilic and leaving-group functionality.

Chemical Formula

CH2ClNO2

Molecular Weight

95.49 g/mol

Functional Groups

Chloro (–Cl) and nitro (–NO2) on a methylene carbon

Aladdin SKU

C1066534

Compound Class

Halonitroalkane (nitrohaloalkane)

Primary Research Use

Electrophilic building block and intermediate in organic synthesis

Physicochemical Properties of Chloronitromethane

Chloronitromethane (CH₂ClNO₂) is a low-molecular-weight halonitroalkane with a molecular weight of approximately 95.49 g/mol. The molecule bears both a chloro substituent and a nitro group on the same carbon, making it a bifunctional compound. This combination confers significant electrophilicity to the methylene carbon, as the electron-withdrawing nitro group activates the carbon toward nucleophilic substitution while the chloride serves as a leaving group.

Chloronitromethane is typically encountered as a colorless to pale-yellow liquid under standard laboratory conditions. It is denser than water and exhibits limited miscibility with water, but is soluble in common polar aprotic and organic solvents such as dichloromethane, acetonitrile, and dimethyl sulfoxide (DMSO). Its vapor pressure and volatility necessitate careful handling in well-ventilated environments.

The simultaneous presence of a nitro group and a halogen on a single carbon imparts unique reactivity, including susceptibility to nucleophilic substitution (S_N2), elimination reactions, and participation in Nef-type transformations. These properties distinguish chloronitromethane from simple alkyl chlorides or nitroalkanes alone.

Synthesis Relevance and Organic Chemistry Applications

Chloronitromethane occupies a specialized niche as a synthetic building block in organic and medicinal chemistry. Its bifunctionality allows it to act as an equivalent of a one-carbon electrophilic unit bearing a masked carbanion functionality (via the nitro group), enabling access to structural motifs that are difficult to achieve through simpler reagents.

Key documented applications include:

• Nitroaldol (Henry) reaction precursors: The nitro group can participate in base-mediated condensations with aldehydes and ketones, generating β-nitro alcohol intermediates that are valuable in natural product and pharmaceutical synthesis.
• Nucleophilic substitution reactions: The chloride leaving group allows displacement by a range of nucleophiles (amines, thiols, alkoxides), enabling diversified library synthesis.
• Preparation of nitromethyl-containing heterocycles: Cyclization reactions incorporating the chloronitromethane scaffold have been used to access nitrogenous heterocyclic frameworks relevant to agrochemical and pharmaceutical research.
• Access to isocyanates and related intermediates: Under appropriate conditions, halonitromethanes can serve as precursors to reactive intermediates in multi-step synthesis.

Researchers in target-oriented synthesis, fragment-based drug discovery, and agrochemical development may find chloronitromethane useful as a readily functionalized one-carbon building block.

Safe Handling, Storage, and Regulatory Considerations

As with all halonitroalkanes, chloronitromethane requires careful handling due to its chemical reactivity and potential health hazards. Researchers should consult the current Safety Data Sheet (SDS) before use. General precautions applicable to this compound class include:

• Personal Protective Equipment (PPE): Use appropriate nitrile or butyl rubber gloves, safety goggles, and a laboratory coat. Work in a fume hood to minimize inhalation exposure given its volatility.
• Storage: Store in a tightly sealed container in a cool, dry, well-ventilated location away from strong bases, reducing agents, and ignition sources. Segregate from incompatible materials in accordance with institutional chemical storage policies.
• Waste disposal: Dispose of chloronitromethane-containing waste in accordance with local, institutional, and national regulations governing halogenated organic solvents and nitro compounds.
• Fire and reactivity hazards: Nitro-containing compounds may pose decomposition risks under extreme heat or in contact with strong reducing agents. Consult the SDS for specific flammability and reactivity data.

Procurement teams should verify current import/export classifications and any controlled-substance or hazardous-material transport requirements applicable in their jurisdiction prior to ordering.

Ordering Chloronitromethane from Aladdin Scientific

Aladdin Scientific supplies chloronitromethane under SKU C1066534. When placing an order, researchers and procurement professionals should note the following:

• Purity and grade: Confirm the specification and purity grade listed on the product page at the time of purchase to ensure suitability for your specific application. Specifications may be updated; always refer to the current certificate of analysis (CoA).
• Quantity and packaging: Select the appropriate pack size for your anticipated usage volume to minimize waste and storage risks associated with prolonged shelf life.
• Shipping: Chloronitromethane is subject to hazardous materials shipping regulations. Aladdin Scientific ships in compliance with applicable transport regulations; delivery timelines may vary based on destination and carrier requirements.
• Returns and questions: For product quality concerns, returns, or technical inquiries, contact Aladdin Scientific customer service through the official website.

Bulk quantity inquiries and custom packaging requests can be directed to the Aladdin Scientific sales team for pricing and availability discussion.

Frequently asked questions

What is chloronitromethane used for in organic chemistry?

Chloronitromethane is used as a bifunctional one-carbon building block in organic synthesis. Its simultaneous chloro and nitro groups enable nucleophilic substitution reactions, participation in Henry (nitroaldol) condensations, and access to heterocyclic scaffolds. It is particularly valuable in pharmaceutical and agrochemical intermediate synthesis.

What safety precautions are required when handling chloronitromethane?

Handlers should wear nitrile or butyl rubber gloves, safety goggles, and a lab coat, and work exclusively in a fume hood. Chloronitromethane should be stored away from strong bases, reducing agents, and ignition sources. Always consult the current Safety Data Sheet (SDS) for compound-specific hazard information before use.

How should chloronitromethane be stored to maintain stability?

Chloronitromethane should be stored in a tightly sealed container in a cool, dry, well-ventilated area, segregated from incompatible materials including strong oxidizers, bases, and reducing agents. Refer to the product's certificate of analysis and SDS for specific recommended storage temperature and shelf-life information.

What is the Aladdin Scientific SKU for chloronitromethane?

Chloronitromethane is available from Aladdin Scientific under SKU C1066534. Researchers can use this SKU to locate the product on the Aladdin website, confirm current specifications, and place orders directly.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for nucleophilic substitution and nitroalkane chemistry.
2. Semmelhack, M. F. et al. Comprehensive Organic Transformations. Wiley-VCH. Reference for haloalkane reactivity and synthetic applications.
3. Aladdin Scientific product page for Chloronitromethane, SKU C1066534. Aladdin Scientific (https://www.aladdin-e.com).

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