4-Bromo-3-Chlorobenzonitrile: Properties, Uses & FAQs

4-Bromo-3-chlorobenzonitrile is a dihalogenated aromatic nitrile building block widely used in pharmaceutical synthesis, agrochemical research, and transition-metal-catalyzed cross-coupling reactions.

CAS Number

41778-73-8

Molecular Formula

C₇H₃BrClN

Molecular Weight

216.46 g/mol

Aladdin SKU

B185310

Functional Groups

Nitrile (–CN), bromo (–Br), chloro (–Cl)

Recommended Storage

Cool, dry, well-ventilated area; away from moisture and light

What Is 4-Bromo-3-Chlorobenzonitrile?

4-Bromo-3-chlorobenzonitrile (CAS 41778-73-8, SKU B185310) is a benzonitrile bearing two halogen substituents: a bromine atom at the 4-position and a chlorine atom at the 3-position of the aromatic ring. The electron-withdrawing nitrile group activates the ring toward nucleophilic aromatic substitution, while the distinct reactivity of the C–Br and C–Cl bonds enables selective, sequential functionalization in synthetic sequences.

The compound appears as a white to off-white crystalline solid at room temperature. Its combination of a versatile nitrile handle, a highly reactive C–Br bond (preferred in oxidative addition to palladium and nickel catalysts), and a moderately reactive C–Cl bond makes it a valuable multi-functional scaffold in medicinal chemistry and materials science.

Key Applications in Research

Pharmaceutical and agrochemical synthesis: The compound serves as a versatile intermediate for constructing heterocyclic frameworks. The nitrile group can be converted to primary amines, tetrazoles, amidines, or carboxylic acids, while the halogens participate in metal-catalyzed coupling reactions to introduce aryl, vinyl, or alkyl substituents.

Cross-coupling chemistry: The C–Br bond undergoes efficient Suzuki–Miyaura, Negishi, Buchwald–Hartwig, and Sonogashira couplings under standard palladium or nickel catalysis. The C–Cl bond can be engaged selectively under more forcing conditions or with specialized ligand systems, enabling orthogonal functionalization of both positions.

Nucleophilic aromatic substitution (SNAr): Activation by the para-cyano group facilitates displacement of the halides by oxygen, nitrogen, or sulfur nucleophiles under appropriate conditions, providing access to ether, amine, and thioether derivatives.

Materials science: Cyano-substituted aromatics are employed as electron-acceptor units in organic electronic materials, dyes, and liquid crystals.

Handling, Storage, and Safety

Personal protective equipment (PPE): Always wear appropriate PPE when handling 4-Bromo-3-chlorobenzonitrile, including nitrile gloves, a laboratory coat, and safety goggles. Work in a well-ventilated fume hood to avoid inhalation of dust or vapors.

Storage: Store the compound in a tightly sealed container in a cool, dry, and well-ventilated area, away from moisture, heat sources, and direct light. Keep away from incompatible materials such as strong oxidizing agents and strong bases.

Disposal: Dispose of waste material in accordance with all applicable local, regional, and national regulations. Do not pour down the drain. Consult the Safety Data Sheet (SDS) for complete hazard and first-aid information before use.

Note: Specific GHS hazard classifications and first-aid measures are detailed in the product SDS. Always consult the SDS prior to handling.

Purity, Grade, and Specifications

Aladdin Scientific offers 4-Bromo-3-chlorobenzonitrile (SKU B185310) for research use. Researchers should confirm the current purity specification and available pack sizes on the product page or by contacting Aladdin's technical support team, as specifications may be updated periodically.

For sensitive synthetic applications, characterization techniques such as GC, HPLC, NMR, and elemental analysis are commonly used to verify reagent purity prior to use. If a certificate of analysis (CoA) is required for your records or regulatory compliance, please request it from Aladdin's customer service team at the time of ordering.

Ordering and Customer Support

How to order: 4-Bromo-3-chlorobenzonitrile is available directly from the Aladdin Scientific website using SKU B185310. You can add the product to your cart, request a bulk quote, or contact the sales team for institutional or volume pricing.

Shipping: Aladdin ships reagents according to applicable transport regulations. Delivery timelines vary by region. Please check the product page for stock availability and estimated lead times before placing your order.

Returns and technical questions: If you have questions about suitability for a specific application, require a CoA, or need to initiate a return, please contact Aladdin's customer service team via the website's support portal. All return and refund requests are processed in accordance with Aladdin's standard returns policy.

Frequently asked questions

What is the CAS number for 4-Bromo-3-chlorobenzonitrile?

The CAS registry number for 4-Bromo-3-chlorobenzonitrile is 41778-73-8. Aladdin Scientific lists this compound under SKU B185310. Always verify the CAS number against the product label and certificate of analysis before use.

Which cross-coupling reactions is 4-Bromo-3-chlorobenzonitrile suitable for?

The C–Br bond of 4-Bromo-3-chlorobenzonitrile readily participates in palladium- and nickel-catalyzed cross-coupling reactions including Suzuki–Miyaura (boronic acids), Negishi (organozinc), Sonogashira (terminal alkynes), and Buchwald–Hartwig (amination) couplings. The less reactive C–Cl bond can be engaged selectively under more forcing conditions or with specialized phosphine or N-heterocyclic carbene (NHC) ligand systems, allowing orthogonal functionalization of both halogen sites.

How should 4-Bromo-3-chlorobenzonitrile be stored to maintain stability?

Store 4-Bromo-3-chlorobenzonitrile in a tightly sealed container in a cool, dry, and well-ventilated location, away from moisture, direct light, and heat. Keep it separated from strong oxidizing agents and strong bases. Under these recommended conditions, the compound is expected to remain stable for an extended period. Always check the product's SDS and CoA for any specific stability data.

Can the nitrile group in 4-Bromo-3-chlorobenzonitrile be further functionalized?

Yes. The nitrile (–CN) group is a versatile synthetic handle that can be transformed into a variety of functional groups under standard conditions. Common transformations include reduction to a primary amine (–CH₂NH₂), hydrolysis to a carboxylic acid (–COOH) or amide (–CONH₂), cycloaddition with azides to form tetrazoles, and conversion to amidines. This versatility makes the compound a useful multi-functional building block in medicinal chemistry.

How do I request a Certificate of Analysis (CoA) for B185310?

To obtain a Certificate of Analysis for 4-Bromo-3-chlorobenzonitrile (SKU B185310), please contact Aladdin Scientific's customer service team through the support portal on the website. Have your lot number ready, as CoAs are issued on a per-lot basis. You may also request the CoA at the time of placing your order.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for cross-coupling and nucleophilic aromatic substitution reactions.
2. 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. General reference for palladium-catalyzed cross-coupling reactions applicable to aryl bromides and chlorides. doi:10.1002/anie.201107017

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