2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile FAQs
2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile FAQs
2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile is a trihalogenated arylacetonitrile building block widely used in pharmaceutical and agrochemical synthesis as a versatile intermediate for further functionalization via the reactive methylene nitrile group.
- CAS-style common name
- 2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile
- Aladdin SKU
- A734994
- Molecular formula
- C8H4BrClFN
- Functional groups
- Aryl bromide, aryl chloride, aryl fluoride, nitrile (–CH2CN)
- Typical applications
- Pharmaceutical intermediates, agrochemical synthesis, heterocycle construction
- Storage recommendation
- Cool, dry, well-ventilated area; away from heat sources and incompatible materials
Chemical Identity and Structure
2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile (Aladdin 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 provides an acidic methylene group whose protons are activated by the adjacent nitrile, making it susceptible to deprotonation and subsequent nucleophilic addition or condensation reactions.
The molecular formula is C8H4BrClFN, and the compound belongs to the broader class of halogenated benzyl nitriles frequently employed as versatile synthetic building blocks. The three halogen substituents offer orthogonal handles for selective cross-coupling reactions (e.g., Suzuki, Negishi, Buchwald–Hartwig) at the C–Br or C–Cl bonds, while the C–F bond can be exploited for nucleophilic aromatic substitution under appropriate conditions.
Handling, Safety, and Storage
As with most arylacetonitrile compounds bearing multiple halogens, appropriate personal protective equipment (PPE) should be worn when handling 2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile. This includes chemical-resistant gloves, safety goggles, and a laboratory coat. Work in a well-ventilated fume hood to minimise inhalation exposure to vapours or dust.
The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated area, away from heat sources, open flames, and incompatible materials such as strong bases, strong oxidisers, and strong reducing agents. Users should consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific prior to use for authoritative hazard classification, first-aid measures, and disposal information.
Waste containing this material must be disposed of in accordance with all applicable local, regional, and national regulations governing halogenated organic waste.
Synthetic Applications and Reactivity
2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile serves as a multifunctional intermediate in medicinal chemistry, agrochemical research, and fine-chemical synthesis. The activated methylene group participates in Knoevenagel condensations, alkylations, and cyclisation reactions to afford heterocyclic scaffolds. The nitrile group itself can be hydrolysed to a carboxylic acid, reduced to an amine, or converted to tetrazoles and amidines, expanding the accessible chemical space from a single starting material.
The aryl bromide is typically the most reactive halogen toward palladium-catalysed cross-coupling under standard conditions, enabling selective introduction of aryl, vinyl, or alkyl groups while leaving the C–Cl and C–F bonds intact for further derivatisation. This orthogonal reactivity makes the compound particularly attractive for multi-step synthesis of complex pharmaceutical and agrochemical targets.
Purity, Specification, and Quality
Aladdin Scientific supplies 2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile under SKU A734994. Researchers and procurement professionals should refer to the current product page or Certificate of Analysis (CoA) for the most up-to-date purity specification, as these values are subject to lot-to-lot verification and may be updated.
When evaluating the suitability of this reagent for a specific application, consider the analytical methods used for purity determination (e.g., GC, HPLC, or NMR). For sensitive catalytic reactions or biological assays, a higher-purity grade may be required. Contact Aladdin Scientific technical support if custom purity or packaging requirements are needed.
Ordering, Availability, and Support
2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile is available from Aladdin Scientific under SKU A734994. To place an order, navigate to the product page on the Aladdin Scientific website, select the desired quantity, and proceed to checkout. Bulk or custom quantities may be available upon request — contact your regional Aladdin Scientific representative or customer service for pricing and lead-time information.
For technical enquiries regarding applications, compatibility, or analytical data, Aladdin Scientific's technical support team can be reached through the contact channels listed on the company website. Certificate of Analysis documents for specific lots can typically be retrieved by entering the lot number on the product page.
Frequently asked questions
What is the molecular formula and molecular weight of 2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile?
The molecular formula of 2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile is C8H4BrClFN. The exact molecular weight should be confirmed from the current Certificate of Analysis or product page, as Aladdin Scientific verifies these values on a per-lot basis.
How should 2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile be stored to maintain stability?
The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated location, away from heat, light, and incompatible materials such as strong bases and oxidisers. Always consult the current SDS for specific storage temperature recommendations and stability data.
Which cross-coupling reactions are most suitable for the aryl halide groups in this compound?
The aryl bromide at the 5-position is typically the most reactive under standard palladium-catalysed conditions (e.g., Suzuki–Miyaura, Negishi, or Buchwald–Hartwig reactions), allowing selective functionalisation while leaving the C–Cl and C–F bonds available for subsequent steps. The C–Cl bond can also be engaged under more forcing palladium or nickel catalysis, and the C–F bond may undergo nucleophilic aromatic substitution with appropriate nucleophiles.
Can the nitrile group in 2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile be further transformed?
Yes. The nitrile group is a versatile functional handle that can be hydrolysed to a carboxylic acid under acidic or basic aqueous conditions, reduced to a primary amine using LiAlH4 or catalytic hydrogenation, or converted to amidines and tetrazoles using appropriate reagents. These transformations significantly broaden the synthetic utility of this compound.
What purity grade is available for SKU A734994, and how can I obtain a Certificate of Analysis?
Purity specifications for A734994 are confirmed on a per-lot basis. Visit the Aladdin Scientific product page for A734994, enter your lot number, and download the corresponding Certificate of Analysis. For specific purity requirements or custom grades, contact Aladdin Scientific customer service directly.
Is 2-(5-Bromo-2-chloro-4-fluorophenyl)acetonitrile available in bulk quantities?
Bulk and custom quantities may be available upon request. Contact your regional Aladdin Scientific sales representative or customer service team with your specific quantity and timeline requirements to obtain a quotation and estimated lead time.
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, 4th ed.; Wiley-Interscience: New York, 1992. (General reference for nitrile and aryl halide reactivity.)
- Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457–2483. (General reference for Suzuki coupling relevant to aryl bromide reactivity.) doi:10.1021/cr00039a007
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