2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile: FAQs & Guide
2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile: FAQs & Guide
2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile is a multi-halogenated arylacetonitrile building block widely employed in medicinal chemistry and fine-chemical synthesis as a versatile electrophilic and nucleophilic intermediate.
- Product Name
- 2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile
- SKU
- A734994
- Molecular Formula
- C8H4BrClFN
- Functional Groups
- Nitrile (–CN), aryl bromide, aryl chloride, aryl fluoride
- Typical Applications
- Pharmaceutical intermediate, cross-coupling substrate, nucleophilic alkylation agent
- Supplier
- Aladdin Scientific
Chemical Identity and Structure
2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile (SKU A734994) is an arylacetonitrile bearing three distinct halogen substituents on the phenyl ring: a bromine at the 5-position, a chlorine at the 2-position, and a fluorine at the 4-position. The acetonitrile (–CH2CN) side chain extends from the 1-position of the ring. This substitution pattern imparts a unique electronic environment to the molecule, making the methylene protons moderately acidic and the nitrile carbon electrophilic toward nucleophiles. The molecular formula is C8H4BrClFN, reflecting the combined molecular weight contributions of the trihalogenated aromatic core and the –CH2CN moiety. The presence of three different halogens provides distinct handles for selective chemoselective transformations in multi-step synthesis.
Physical Properties and Storage
2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile is typically encountered as a solid or low-melting crystalline material at room temperature, consistent with arylacetonitrile compounds of comparable molecular weight. It should be stored in a cool, dry, well-ventilated location, away from heat sources, strong oxidizers, and bases, which could promote hydrolysis of the nitrile group or deprotonation of the acidic methylene. The compound should be kept in a tightly sealed container to prevent moisture uptake and degradation. Long-term storage under inert atmosphere (nitrogen or argon) at 2–8 °C or as recommended on the product label is advised to maintain purity. Specific melting point, boiling point, and density values should be confirmed from the certificate of analysis supplied with SKU A734994.
Synthetic Applications and Reactivity
The compound serves as a multifunctional building block in organic and medicinal chemistry. The –CH2CN group can participate in base-mediated alkylations, Knoevenagel condensations, and cycloaddition reactions, while the nitrile itself can be hydrolyzed to a carboxylic acid, reduced to an amine, or converted to heterocyclic systems such as imidazoles and tetrazoles. The aryl bromide at the 5-position is the most reactive halogen toward palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Negishi, Sonogashira), enabling selective functionalization while the aryl chloride and fluoride remain intact for subsequent transformations or serve as pharmacophoric elements. The aryl fluoride can participate in nucleophilic aromatic substitution (SNAr) under appropriate conditions. This combination of reactivity makes 2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile particularly valuable in the construction of complex pharmaceutical scaffolds.
Safety and Handling
As a halogenated organic nitrile, 2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile should be handled with appropriate personal protective equipment (PPE), including nitrile gloves, safety glasses, and a laboratory coat. Work should be performed in a well-ventilated fume hood to minimize inhalation of dust or vapors. Nitrile-containing compounds may release hydrogen cyanide under strongly acidic or high-temperature conditions; however, arylacetonitriles are generally of lower volatility and acute toxicity than simple alkyl nitriles. Disposal must comply with local and institutional regulations for halogenated organic waste. Refer to the Safety Data Sheet (SDS) provided by Aladdin Scientific for SKU A734994 for complete hazard classification, first-aid measures, and regulatory information before use.
Ordering and Quality Information
2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile is available from Aladdin Scientific under SKU A734994. Each lot is supplied with a certificate of analysis (CoA) confirming identity (typically by NMR or HPLC), purity, and appearance. Researchers requiring custom quantities or higher-purity grades are encouraged to contact Aladdin Scientific's technical sales team. For procurement teams, the SKU can be used for direct ordering through the Aladdin Scientific online platform or via purchase order. Ensure that the correct SKU (A734994) is referenced in all orders to avoid confusion with structurally similar arylacetonitrile analogues. Bulk pricing and availability can be confirmed through the Aladdin Scientific website or customer service.
Frequently asked questions
What is 2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile used for in synthesis?
It is primarily used as a multi-functional building block in medicinal chemistry and fine-chemical synthesis. The aryl bromide enables palladium-catalyzed cross-coupling reactions, the nitrile group can be transformed into acids, amines, or heterocycles, and the active methylene participates in condensation and alkylation reactions, making it valuable for constructing complex pharmaceutical scaffolds.
How should 2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile be stored to maintain its purity?
The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated area, away from heat, moisture, strong oxidizers, and bases. Long-term storage under an inert atmosphere (nitrogen or argon) at 2–8 °C is recommended. Always consult the certificate of analysis and SDS supplied with SKU A734994 for lot-specific storage guidance.
Which halogen on the aryl ring is most reactive toward cross-coupling reactions?
The aryl bromide at the 5-position is the most reactive toward palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura, Negishi, and Sonogashira couplings. The aryl chloride and aryl fluoride are less reactive under standard coupling conditions and can be retained for orthogonal subsequent transformations or serve as pharmacophoric substituents.
What safety precautions should be taken when handling this compound?
Use appropriate PPE including nitrile gloves, safety glasses, and a laboratory coat, and work in a well-ventilated fume hood. As a halogenated nitrile, it should be treated with care; refer to the SDS for SKU A734994 for full hazard information, first-aid procedures, and disposal regulations before use.
How can I confirm the identity and purity of the product upon receipt?
Each lot of SKU A734994 from Aladdin Scientific is accompanied by a certificate of analysis (CoA) that provides identity confirmation (typically by NMR spectroscopy or HPLC) and purity data. Customers can also request the CoA through the Aladdin Scientific website or contact customer service for lot-specific documentation.
References
- Aladdin Scientific product page for 2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile, SKU A734994.
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley, 4th ed. General reactivity of arylacetonitriles and haloarenes in cross-coupling and substitution reactions.
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry. Oxford University Press, 2nd ed. Nitrile chemistry: hydrolysis, reduction, and heterocycle formation.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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