4-Bromo-2-(trifluoromethoxy)benzonitrile: Properties & Uses

4-Bromo-2-(trifluoromethoxy)benzonitrile is a fluorinated aromatic building block bearing both a bromo and a trifluoromethoxy substituent on the benzonitrile core, making it a versatile intermediate for medicinal chemistry and cross-coupling synthesis.

CAS / SKU

Aladdin SKU B732658

Molecular Formula

C8H3BrF3NO

Molecular Weight

266.01 g/mol

Key Functional Groups

Bromo (C–Br), trifluoromethoxy (–OCF3), nitrile (–CN)

Primary Application

Synthetic intermediate in medicinal chemistry and agrochemical research

Recommended Storage

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

Chemical Identity and Structure

4-Bromo-2-(trifluoromethoxy)benzonitrile (Aladdin SKU B732658) is an aromatic compound with the molecular formula C₈H₃BrF₃NO and a molecular weight of approximately 266.01 g/mol. Its structure consists of a benzene ring substituted at the 1-position with a nitrile group (–CN), at the 2-position with a trifluoromethoxy group (–OCF₃), and at the 4-position with a bromine atom.

The combination of three electron-withdrawing groups—nitrile, trifluoromethoxy, and bromo—renders the aromatic ring strongly electron-deficient. The –OCF₃ group in particular confers high lipophilicity and metabolic stability, properties that are highly valued in drug discovery programs targeting improved bioavailability and pharmacokinetic profiles.

Synthetic Applications and Reactivity

The aryl bromide moiety in 4-Bromo-2-(trifluoromethoxy)benzonitrile is an excellent handle for transition-metal-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Buchwald–Hartwig, Negishi, and Sonogashira couplings. These transformations allow researchers to rapidly build structural complexity around the fluorinated aromatic core.

The nitrile group provides further elaboration possibilities: it can be hydrolyzed to a carboxylic acid, reduced to an amine, converted to a tetrazole (a common carboxylic acid bioisostere), or used in nucleophilic addition reactions. This multifunctionality makes the compound a highly efficient scaffold for library synthesis in medicinal and agrochemical research.

The strongly electron-withdrawing character of the ring also facilitates nucleophilic aromatic substitution (SNAr) at the position bearing the bromine, particularly under forcing conditions or with activated nucleophiles.

Handling, Safety, and Storage

As with all halogenated aromatic nitriles, appropriate personal protective equipment (PPE) including laboratory coat, chemical-resistant gloves, and safety glasses should be worn when handling 4-Bromo-2-(trifluoromethoxy)benzonitrile. Work should be conducted in a well-ventilated fume hood to minimize inhalation exposure to dust or vapors.

The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated area, away from moisture, heat sources, and incompatible materials such as strong oxidizers, strong bases, and reducing agents. Refer to the Safety Data Sheet (SDS) provided with the product for complete hazard information, first-aid measures, and disposal guidance before use.

In case of skin or eye contact, flush thoroughly with water and seek medical advice. Do not dispose of the compound via drains; follow local regulations for chemical waste disposal.

Purity, Specification, and Quality

Aladdin Scientific supplies 4-Bromo-2-(trifluoromethoxy)benzonitrile (SKU B732658) to research-grade specifications. Lot-specific purity data, including NMR, GC, or HPLC analysis results where applicable, are provided on the Certificate of Analysis (CoA) that accompanies each shipment.

Researchers requiring the CoA for a specific lot number can request it through Aladdin's customer service portal or by contacting the technical support team directly. It is recommended to verify purity prior to use in sensitive synthetic or biological assays to ensure reproducibility of results.

Ordering and Customer Support

4-Bromo-2-(trifluoromethoxy)benzonitrile is available from Aladdin Scientific under SKU B732658. To place an order, visit the Aladdin Scientific website, search by product name or SKU, and add the desired quantity to your cart. Bulk or custom quantities may be available; contact the sales team for pricing and lead-time information.

For technical questions regarding applications, compatibility, or analytical data, please reach out to Aladdin's technical support team. For queries related to shipping, returns, payments, or account management, the customer service team is available through the contact channels listed on the Aladdin Scientific website.

Frequently asked questions

What is 4-Bromo-2-(trifluoromethoxy)benzonitrile used for in research?

It is primarily used as a synthetic building block in medicinal chemistry and agrochemical research. The aryl bromide enables transition-metal-catalyzed cross-coupling reactions (e.g., Suzuki, Buchwald–Hartwig), while the nitrile group can be further transformed into amines, tetrazoles, or carboxylic acids. The trifluoromethoxy group adds lipophilicity and metabolic stability to target molecules.

How should I store 4-Bromo-2-(trifluoromethoxy)benzonitrile to maintain its integrity?

Store the compound in a tightly sealed container in a cool, dry, and well-ventilated area, away from moisture, strong oxidizers, strong bases, and ignition sources. Always consult the Safety Data Sheet (SDS) provided with the product for complete storage and handling guidance.

What Aladdin SKU corresponds to 4-Bromo-2-(trifluoromethoxy)benzonitrile?

4-Bromo-2-(trifluoromethoxy)benzonitrile is available from Aladdin Scientific under SKU B732658. You can search this SKU directly on the Aladdin Scientific website to view availability, pricing, and specification details.

Can I obtain a Certificate of Analysis (CoA) for a specific lot of B732658?

Yes. Lot-specific Certificates of Analysis are available for all Aladdin Scientific products including B732658. You can request a CoA through the Aladdin Scientific customer service portal or by contacting technical support with your lot number.

Is 4-Bromo-2-(trifluoromethoxy)benzonitrile compatible with nucleophilic aromatic substitution reactions?

Yes. The strongly electron-withdrawing nitrile and trifluoromethoxy groups render the aromatic ring electron-deficient, facilitating nucleophilic aromatic substitution (SNAr) at the position bearing the bromine atom, particularly with activated nucleophiles or under forcing conditions.

References

1. Aladdin Scientific product page for 4-Bromo-2-(trifluoromethoxy)benzonitrile, SKU B732658.
2. General reference: Fluorine in Medicinal Chemistry and Chemical Biology, ed. I. Ojima, Wiley-Blackwell, 2009. (Textbook-level source for OCF3 group properties in drug discovery.)

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