3-Bromo-2-Fluorobenzonitrile: Properties, Uses & FAQs

3-Bromo-2-fluorobenzonitrile is a halogenated aromatic building block widely used in pharmaceutical synthesis and cross-coupling chemistry due to the complementary reactivity of its bromo, fluoro, and nitrile functional groups.

IUPAC Name

3-Bromo-2-fluorobenzonitrile

CAS Number

179107-45-0

Molecular Formula

C7H3BrFN

Molecular Weight

200.01 g/mol

Functional Groups

Nitrile (–CN), Bromo (–Br), Fluoro (–F) on a benzene ring

SKU

B186845

Primary Application

Synthetic building block for medicinal chemistry and agrochemical research

Chemical Identity and Structure

3-Bromo-2-fluorobenzonitrile (CAS 179107-45-0, SKU B186845) is an ortho/meta-disubstituted benzonitrile bearing a bromine atom at the 3-position and a fluorine atom at the 2-position relative to the nitrile group. Its molecular formula is C₇H₃BrFN with a molecular weight of approximately 200.01 g/mol. The combination of three distinct functional groups on a single aromatic ring makes this compound a versatile and differentiated synthetic intermediate.

The electron-withdrawing nitrile group and fluorine substituent jointly reduce the electron density of the ring, influencing both the regioselectivity of further electrophilic or nucleophilic substitution reactions and the reactivity of the carbon–halogen bonds. The aryl bromide bond is particularly amenable to metal-catalyzed cross-coupling reactions, while the aryl fluoride bond can participate in nucleophilic aromatic substitution (SNAr) under appropriate conditions.

Synthetic Applications

3-Bromo-2-fluorobenzonitrile serves as a key building block in several important synthetic transformations:

• Palladium-catalyzed cross-coupling: The C–Br bond undergoes Suzuki–Miyaura, Negishi, Stille, and Buchwald–Hartwig amination reactions, enabling the introduction of aryl, alkenyl, alkyl, or amino groups at the 3-position.
• Nucleophilic aromatic substitution (SNAr): The fluorine at the 2-position, activated by the adjacent electron-withdrawing nitrile group, can be displaced by amines, alkoxides, or thiolates to produce 2-substituted-3-bromobenzonitrile derivatives.
• Nitrile group transformations: The –CN group can be hydrolyzed to a carboxylic acid, reduced to an amine, or converted to a tetrazole ring, providing further diversification of the scaffold.
• Sequential functionalization: The distinct reactivity of the Br and F substituents allows chemoselective, stepwise functionalization of the same ring, making this compound highly valuable in library synthesis and lead optimization.

These properties make 3-Bromo-2-fluorobenzonitrile a frequently encountered intermediate in the synthesis of pharmaceuticals, agrochemicals, and functional materials.

Handling, Storage, and Safety

As with most halogenated aromatic nitriles, appropriate laboratory precautions should be observed when working with 3-Bromo-2-fluorobenzonitrile:

• Personal protective equipment (PPE): Wear chemically resistant gloves, safety goggles, and a laboratory coat. Work in a well-ventilated fume hood to minimize inhalation exposure.
• Storage: Store in a tightly sealed container in a cool, dry, and well-ventilated area, away from moisture, oxidizing agents, and strong bases. Refrigerated storage (2–8 °C) is recommended to maintain long-term stability.
• Disposal: Dispose of as halogenated organic waste in accordance with local institutional and governmental regulations.
• First aid: In case of skin or eye contact, flush immediately with copious water. Seek medical advice if irritation persists.

Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use. Specific hazard classifications and GHS pictograms are detailed in the SDS for SKU B186845.

Purity, Specification, and Quality Assurance

Aladdin Scientific supplies 3-Bromo-2-fluorobenzonitrile (SKU B186845) as a research-grade reagent. The compound is characterized and quality-controlled using standard analytical techniques including:

• NMR spectroscopy (¹H, ¹³C, ¹⁹F) to confirm structural identity and assess purity.
• GC or HPLC analysis to quantify chemical purity.
• Mass spectrometry to confirm the correct molecular ion consistent with C₇H₃BrFN (MW ≈ 200.01 g/mol).

Customers requiring a Certificate of Analysis (CoA) for a specific lot may request this document through Aladdin Scientific's customer service portal. Lot-specific purity data and analytical results are provided upon request. Please refer to the product page for current specification details.

Frequently asked questions

What is 3-Bromo-2-fluorobenzonitrile used for in organic synthesis?

3-Bromo-2-fluorobenzonitrile is primarily used as a multifunctional building block in medicinal chemistry, agrochemical research, and materials science. Its aryl bromide undergoes palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Buchwald–Hartwig), while the activated aryl fluoride participates in nucleophilic aromatic substitution (SNAr). The nitrile group can also be further transformed into carboxylic acids, amines, or heterocycles.

How should 3-Bromo-2-fluorobenzonitrile be stored to maintain stability?

This compound should be stored in a tightly sealed container under cool, dry, and well-ventilated conditions, away from moisture and incompatible reagents such as strong bases and oxidizing agents. Refrigerated storage at 2–8 °C is generally recommended to maximize long-term stability. Always check the Aladdin Scientific SDS for lot-specific storage guidance.

Can I selectively react the bromine without affecting the fluorine substituent in 3-Bromo-2-fluorobenzonitrile?

Yes. The C–Br bond is significantly more reactive than the C–F bond toward oxidative addition to palladium(0) catalysts, making it possible to perform chemoselective palladium-catalyzed cross-coupling reactions at the bromine position while leaving the aryl fluoride intact. This chemoselectivity is well-established in the cross-coupling literature and is one of the key synthetic advantages of this building block.

What analytical methods confirm the identity and purity of SKU B186845?

Identity and purity of 3-Bromo-2-fluorobenzonitrile (SKU B186845) are typically confirmed by a combination of 1H, 13C, and 19F NMR spectroscopy, GC or HPLC purity analysis, and mass spectrometry. A lot-specific Certificate of Analysis (CoA) can be requested from Aladdin Scientific customer service.

Is 3-Bromo-2-fluorobenzonitrile hazardous, and what precautions are needed?

As a halogenated aromatic nitrile, 3-Bromo-2-fluorobenzonitrile should be handled with appropriate caution. Use chemically resistant gloves, safety goggles, and a laboratory coat, and work in a fume hood. Consult the full Safety Data Sheet (SDS) for SKU B186845 available from Aladdin Scientific for complete hazard classifications, GHS pictograms, and first-aid measures.

References

1. Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize. Angew. Chem. Int. Ed. 2012, 51, 5062–5085. doi:10.1002/anie.201107017
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for SNAr and nitrile chemistry.)
3. Hartwig, J. F. Organotransition Metal Chemistry: From Bonding to Catalysis; University Science Books: Sausalito, CA, 2010. (Reference for chemoselectivity of C–Br vs C–F in cross-coupling.)

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.