2-(2-Bromo-5-fluorophenyl)acetonitrile: Properties & Lab Use

2-(2-Bromo-5-fluorophenyl)acetonitrile is a halogenated arylacetonitrile building block widely used in organic synthesis as a versatile intermediate for the preparation of pharmaceuticals, agrochemicals, and fine chemicals.

Chemical Name

2-(2-Bromo-5-fluorophenyl)acetonitrile

CAS Number

Need verification — see review flags

Molecular Formula

C8H5BrFN

Molecular Weight

214.04 g/mol (needs verification)

Functional Groups

Nitrile (–CN), aryl bromide (C–Br), aryl fluoride (C–F)

SKU

B590558

Key Application

Pharmaceutical and agrochemical intermediate; cross-coupling substrate

What Is 2-(2-Bromo-5-fluorophenyl)acetonitrile?

2-(2-Bromo-5-fluorophenyl)acetonitrile (SKU B590558) is an arylacetonitrile derivative bearing two halogen substituents on the phenyl ring: a bromine atom at the ortho position (C-2) and a fluorine atom at the meta position relative to the acetonitrile group (C-5). The combination of an activated methylene nitrile group and two distinct halogens makes this compound a highly versatile bifunctional building block in synthetic chemistry.

The nitrile group contributes significant electron-withdrawing character, rendering the benzylic methylene protons relatively acidic and amenable to deprotonation and subsequent alkylation or condensation reactions. Meanwhile, the aryl bromide serves as a handle for transition-metal-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Negishi, Buchwald–Hartwig amination, and palladium-catalyzed carbonylation. The aryl fluoride can participate in nucleophilic aromatic substitution (SNAr) under appropriate conditions.

Handling, Storage, and Safety

As with all aryl nitrile and organobromine compounds, appropriate laboratory safety precautions must be observed when working with 2-(2-Bromo-5-fluorophenyl)acetonitrile. Researchers should consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific before use. General precautions include working in a well-ventilated fume hood, wearing appropriate personal protective equipment (PPE) including chemically resistant gloves, lab coat, and safety goggles.

The compound should be stored in a tightly sealed container away from moisture, heat, and incompatible materials such as strong oxidizers and strong bases. Cool, dry storage conditions (typically 2–8 °C or as specified on the product label) are recommended to maintain long-term stability and reagent quality. Always verify specific storage requirements on the current product label and SDS, as conditions may be updated.

Note: Nitrile-containing compounds may release toxic hydrogen cyanide (HCN) upon thermal decomposition or contact with strong acid. Ensure appropriate waste disposal procedures are followed in accordance with local regulations.

Synthetic Applications and Use Cases

The bifunctional nature of 2-(2-Bromo-5-fluorophenyl)acetonitrile makes it a valuable intermediate across multiple synthetic strategies:

• Cross-coupling reactions: The aryl C–Br bond undergoes efficient palladium- or nickel-catalyzed cross-coupling (e.g., Suzuki–Miyaura with boronic acids, Negishi with organozinc reagents) to introduce aryl, vinyl, or alkyl groups at the 2-position of the phenyl ring.
• Knoevenagel condensation: The acidic benzylic methylene can condense with aldehydes in the presence of a base to yield α,β-unsaturated nitrile derivatives useful in further transformations.
• Cyclization reactions: The combined reactivity of the nitrile, the benzylic CH2, and the aryl halide enables intramolecular cyclization strategies to construct heterocyclic scaffolds relevant to medicinal chemistry.
• SNAr reactions: The electron-deficient aryl fluoride (activated by the ortho-bromo and the nitrile-bearing side chain) can undergo nucleophilic aromatic substitution with amines, alkoxides, or thiolates under suitable conditions.

These applications make the compound particularly relevant in the preparation of drug candidates, crop-protection molecules, and advanced material precursors.

Purity, Quality, and Ordering Information

Aladdin Scientific offers 2-(2-Bromo-5-fluorophenyl)acetonitrile under SKU B590558. Researchers and procurement teams should refer to the current product page for up-to-date specifications including purity grade, available pack sizes, lot-specific certificates of analysis (CoA), and pricing. Lot-specific CoA documents confirm analytical data such as purity by GC or HPLC, NMR characterization, and appearance.

For bulk inquiries, custom synthesis, or questions about specification requirements for GMP or regulated workflows, please contact Aladdin Scientific's technical support or sales team directly. Aladdin Scientific's quality management processes are designed to support reproducible research outcomes.

Frequently Asked Questions at a Glance

The FAQ section below addresses the most common questions received from researchers and lab managers regarding the properties, handling, and synthetic use of 2-(2-Bromo-5-fluorophenyl)acetonitrile. If your question is not covered, please contact Aladdin Scientific technical support for personalised assistance.

Frequently asked questions

What are the primary synthetic uses of 2-(2-Bromo-5-fluorophenyl)acetonitrile?

This compound serves as a bifunctional building block in pharmaceutical and agrochemical synthesis. The aryl bromide is commonly employed in palladium-catalyzed cross-coupling reactions (e.g., Suzuki–Miyaura, Buchwald–Hartwig amination), while the activated benzylic nitrile participates in Knoevenagel condensations, alkylations, and cyclization reactions. The aryl fluoride may also undergo SNAr reactions with suitable nucleophiles.

How should 2-(2-Bromo-5-fluorophenyl)acetonitrile be stored to maintain stability?

The compound should be stored in a tightly sealed container under cool, dry conditions, away from moisture, light, strong oxidizers, and strong bases. Refrigerated storage (2–8 °C) is generally recommended for arylacetonitrile reagents, but researchers should always verify the exact conditions specified on the current Aladdin Scientific product label and SDS for lot-specific guidance.

What safety precautions should I follow when handling this compound?

Always handle 2-(2-Bromo-5-fluorophenyl)acetonitrile in a well-ventilated fume hood, wearing chemically resistant gloves, a lab coat, and safety goggles. Consult the current SDS before use, as nitrile-containing compounds can release toxic HCN upon thermal decomposition or exposure to strong acids. Dispose of waste in accordance with local environmental and safety regulations.

Can the aryl fluoride in this molecule be selectively functionalized independently of the aryl bromide?

Yes, in principle: the aryl bromide and aryl fluoride exhibit different reactivity profiles. The C–Br bond is preferentially reactive in oxidative addition steps of palladium-catalyzed cross-couplings, while the aryl fluoride is better suited for SNAr reactions with hard nucleophiles such as amines or alkoxides, particularly when further activated by electron-withdrawing groups. Careful choice of reaction conditions allows sequential or selective functionalization of each halogen. Researchers should consult primary literature for specific reaction optimization.

How do I request a Certificate of Analysis (CoA) or technical specifications for SKU B590558?

Certificates of Analysis and detailed technical specifications for B590558 can be requested through the Aladdin Scientific website product page or by contacting customer service directly with your lot number. The CoA typically includes purity data (GC or HPLC), NMR confirmation, molecular weight, and appearance details specific to the manufactured batch.

Is 2-(2-Bromo-5-fluorophenyl)acetonitrile available in bulk or custom quantities?

For bulk quantities or custom packaging requirements beyond standard catalog offerings, researchers and procurement teams should contact Aladdin Scientific's sales team directly to discuss availability, lead times, and pricing. Custom synthesis or tailored specifications for regulated (e.g., GMP) applications may also be arranged upon inquiry.

References

1. Aladdin Scientific product page: 2-(2-Bromo-5-fluorophenyl)acetonitrile, SKU B590558. Aladdin Scientific.
2. Safety Data Sheet: 2-(2-Bromo-5-fluorophenyl)acetonitrile. Aladdin Scientific. (Current edition — consult supplier for latest version.)
3. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. (Standard reference for nitrile and aryl halide reactivity — edition and page numbers not specified.)

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