Introduction and Chemical Overview

5-Bromofuran-2-carbonitrile (CAS number needs confirmation; SKU B698780) is a difunctionalized aromatic heterocycle featuring both an aryl bromide and a nitrile group on a furan ring. The electron-withdrawing nitrile at the 2-position activates the ring toward nucleophilic processes and directs regioselectivity, while the bromine at the 5-position serves as a versatile handle for transition-metal-catalyzed cross-coupling reactions (e.g., Suzuki–Miyaura, Negishi, Buchwald–Hartwig) and halogen–metal exchange reactions. This combination of orthogonal reactive sites makes 5-Bromofuran-2-carbonitrile a valuable building block in medicinal chemistry, agrochemical research, and materials science.

The nitrile group can be further elaborated to amidines, tetrazoles, amines, or carboxylic acids, providing rich downstream synthetic diversity from a single starting material.

Safety and Handling Precautions

Before working with 5-Bromofuran-2-carbonitrile, consult the Safety Data Sheet (SDS) supplied with product SKU B698780. The following general precautions apply:

• Personal Protective Equipment (PPE): Wear nitrile gloves, a lab coat, and safety goggles at all times. Use additional face protection if working with larger quantities.
• Ventilation: Handle exclusively inside a certified chemical fume hood. Nitrile-bearing compounds may release hydrogen cyanide (HCN) upon decomposition; adequate ventilation is critical.
• Skin and Eye Contact: Avoid all contact. In case of skin contact, wash thoroughly with soap and water for at least 15 minutes. For eye contact, irrigate immediately with copious water and seek medical attention.
• Inhalation: Do not inhale dust or vapors. If inhalation occurs, move to fresh air immediately and seek medical advice.
• Ingestion: Do not eat, drink, or smoke when handling this compound. Seek immediate medical assistance if ingested.
• Waste Disposal: Dispose of all waste in accordance with local, regional, and national regulations for halogenated and nitrile-containing organic waste.

Note: Specific GHS hazard classifications should be verified from the official SDS for B698780 before use.

Storage Protocol

Proper storage preserves the chemical integrity of 5-Bromofuran-2-carbonitrile and ensures reproducible results in downstream applications.

1. Temperature: Store at room temperature (15–25 °C) in a cool, dry location, or as specified on the product label. Avoid exposure to heat sources.
2. Light: Protect from direct light; store in amber vials or in a darkened cabinet to prevent photodegradation.
3. Moisture: Keep the container tightly sealed. Use desiccant (silica gel or molecular sieves) in the storage area if ambient humidity is high, as moisture can hydrolyze the nitrile group over extended periods.
4. Atmosphere: For long-term storage or after partial use, consider back-filling the headspace with dry nitrogen or argon before resealing to minimize oxidative degradation.
5. Segregation: Store away from strong oxidizers, strong bases, and reducing agents. Keep away from incompatible materials as specified in the SDS.
6. Labeling: Ensure all containers remain clearly labeled with the compound name, CAS number, lot number, date received, and date opened.

Under recommended conditions, shelf life is expected to be at least 12 months, but this should be confirmed against the certificate of analysis (CoA) for each specific lot (B698780).

Suggested Laboratory Applications and Reaction Protocols

5-Bromofuran-2-carbonitrile participates in a range of synthetic transformations. The following outlines general protocol considerations for its most common applications.

1. Suzuki–Miyaura Cross-Coupling

The C–Br bond undergoes palladium-catalyzed coupling with aryl or heteroaryl boronic acids. Typical conditions include a Pd(0) or Pd(II) precatalyst (e.g., Pd(PPh₃)₄, Pd(dppf)Cl₂), an inorganic base (K₂CO₃ or Cs₂CO₃), and an aqueous/organic co-solvent system (e.g., DMF/H₂O or dioxane/H₂O) at 80–100 °C under nitrogen or argon atmosphere.

2. Halogen–Lithium Exchange

Treatment with n-BuLi (2.5 M in hexanes) at –78 °C in anhydrous THF affords the 5-lithiofuran-2-carbonitrile intermediate, which can be quenched with electrophiles (aldehydes, ketones, trimethylsilyl chloride, etc.) to introduce diverse substituents at C-5.

3. Nitrile Group Transformations

• Hydrolysis: Reflux in aqueous acid or base yields the corresponding furan-2-carboxylic acid derivative.
• Reduction: LiAlH₄ in anhydrous THF or catalytic hydrogenation affords the aminomethyl (–CH₂NH₂) product.
• Cycloaddition to Tetrazole: Reaction with sodium azide (NaN₃) and ammonium chloride in DMF at elevated temperature provides 5-(2H-tetrazol-5-yl)furan derivatives.

General Caution: All reactions involving aryllithium species or strong reducing agents must be conducted under strict anhydrous, inert-atmosphere conditions with appropriate cryogenic equipment.

Quality Control and Verification

Before use in sensitive synthetic campaigns, confirm the identity and purity of 5-Bromofuran-2-carbonitrile (B698780) using standard analytical techniques:

• ¹H NMR: Characteristic aromatic protons of the furan ring are expected near δ 7.0–7.5 ppm. Absence of unexpected peaks confirms purity.
• ¹³C NMR / IR: The nitrile stretch appears at approximately 2220–2230 cm⁻¹ in the IR spectrum; the carbonyl-like CN carbon appears near δ 115 ppm in ¹³C NMR.
• GC or HPLC: Run against the lot-specific certificate of analysis (CoA) to verify stated purity (typically ≥97% or as declared).
• Mass Spectrometry: ESI-MS or EI-MS should show the expected molecular ion cluster with characteristic bromine isotope pattern (M and M+2 in approximately 1:1 ratio).
• Melting Point: Verify against the stated value on the CoA; deviations may indicate decomposition or impurity.

Contact Aladdin Scientific customer support if analytical results deviate significantly from CoA specifications for lot B698780.