Chemical Identity and Physical Properties

5-Nitro-2-furaldoxime is an organic compound belonging to the nitrofuran family. It is formed by the condensation of 5-nitro-2-furaldehyde with hydroxylamine, introducing an oxime functional group (–CH=N–OH) in place of the aldehyde carbonyl. The molecule retains the electron-deficient furan ring bearing a nitro substituent at the 5-position, which confers significant electrophilic character and underpins its biological and chemical reactivity.

The compound is typically obtained as a solid (often pale yellow to yellow crystals), consistent with other nitrofuran derivatives. The nitro group and the conjugated oxime moiety together contribute to its UV-absorbing characteristics, making it amenable to spectrophotometric detection. Researchers should consult the product specification sheet (Certificate of Analysis) provided with each lot of Aladdin SKU N356796 for confirmed physical constants such as melting point and purity.

Research Applications

Antimicrobial and Biological Research: Nitrofuran derivatives have a well-documented history as antimicrobial agents. The nitro group is considered central to their bioactivity, as it undergoes reductive activation within microbial cells to generate reactive intermediates that damage DNA and other macromolecules. 5-Nitro-2-furaldoxime has been investigated in the context of structure–activity relationship (SAR) studies aimed at understanding how structural modifications to the nitrofuran scaffold affect antimicrobial potency and selectivity.

Organic Synthesis: As an aldoxime, 5-Nitro-2-furaldoxime can serve as a precursor or building block in the preparation of more complex nitrogen-containing heterocycles, nitriles (via dehydration), and other functionalized compounds. Its electrophilic aromatic ring makes it a useful scaffold for further derivatization.

Analytical and Coordination Chemistry: Oxime-containing compounds are classical ligands for transition-metal complexation. 5-Nitro-2-furaldoxime may be employed in coordination chemistry studies to form metal complexes, with potential characterization by UV-Vis spectrophotometry, IR spectroscopy, and X-ray crystallography. Additionally, its UV absorption profile can be exploited in colorimetric or spectrophotometric assay development.

Safe Handling, Storage, and Disposal

Personal Protective Equipment (PPE): Always wear appropriate PPE when handling 5-Nitro-2-furaldoxime, including chemical-resistant gloves, a laboratory coat, and safety spectacles or goggles. If dust or aerosol generation is possible, use a certified fume hood and consider respiratory protection.

Storage: Store the compound in a tightly sealed container in a cool, dry, and well-ventilated area, protected from direct light. Keep away from strong oxidising agents, strong acids, and strong bases. Follow your institution's chemical inventory management protocols.

Spill and Waste Disposal: In the event of a spill, avoid generating dust, sweep up carefully, and dispose of in accordance with local, regional, and national regulations governing nitro-aromatic compounds. Do not dispose of via drain or general waste. Consult the Safety Data Sheet (SDS) for lot-specific hazard classifications and first-aid measures before beginning any experimental work. The SDS for Aladdin SKU N356796 is available from Aladdin Scientific upon request.

Laboratory Protocol: Preparing Stock Solutions

The following represents general best-practice guidance. Always verify solubility and compatibility with your specific experimental system before use.

1. Solvent Selection: 5-Nitro-2-furaldoxime, like many nitrofuran derivatives, may show limited aqueous solubility. Dimethyl sulfoxide (DMSO) or dimethylformamide (DMF) are commonly employed as co-solvents for nitrofuran compounds. Confirm solubility empirically at the concentration required for your assay.
2. Weighing: Tare a clean, dry microcentrifuge tube or glass vial. Weigh the required amount of 5-Nitro-2-furaldoxime using a calibrated analytical balance inside a fume hood to minimise dust exposure.
3. Dissolution: Add the appropriate volume of solvent gradually with vortexing or gentle sonication until complete dissolution is achieved. For aqueous buffers, add the organic solvent stock dropwise to aqueous media while mixing to avoid precipitation.
4. Concentration Verification: Where critical, verify stock concentration by UV-Vis spectrophotometry using the compound's known absorption maximum. Record the actual concentration on the stock tube label.
5. Storage of Stock: Aliquot to minimise freeze-thaw cycles. Store aliquots at –20 °C protected from light unless otherwise validated. Record preparation date and expiry on each aliquot.