2-Bromo-6-fluorobenzotrifluoride: Properties, Handling & Lab Use
2-Bromo-6-fluorobenzotrifluoride: Properties, Handling & Lab Use
2-Bromo-6-fluorobenzotrifluoride is a halogenated, fluorine-rich aromatic building block widely employed in pharmaceutical and agrochemical research as a versatile electrophilic coupling partner and synthetic intermediate.
- Chemical Name
- 2-Bromo-6-fluorobenzotrifluoride
- CAS Number
- Not confirmed in source material — see review flag
- Molecular Formula
- C7H3BrF4
- Functional Groups
- Aryl bromide, aryl fluoride, trifluoromethyl group
- Key Application
- Electrophilic aromatic building block for cross-coupling and nucleophilic aromatic substitution reactions
- Storage Recommendation
- Store in a cool, dry, well-ventilated area away from moisture and ignition sources
Chemical Identity and Physical Properties
2-Bromo-6-fluorobenzotrifluoride is an aromatic organofluorine compound bearing three distinct halogen-derived substituents on a benzene ring: a bromine atom at the 2-position, a fluorine atom at the 6-position, and a trifluoromethyl (–CF3) group. Its molecular formula is C7H3BrF4, combining the strong electron-withdrawing character of both the fluorine substituent and the trifluoromethyl group with the synthetic versatility of the aryl bromide handle.
The trifluoromethyl group imparts significant lipophilicity and metabolic stability to molecules in which this scaffold is incorporated, properties that are particularly valued in medicinal chemistry and agrochemical design. The coexistence of an aryl bromide and an aryl fluoride on the same ring provides orthogonal sites for selective functionalization, making this reagent a multifunctional intermediate for sequential synthetic transformations.
Specific physical constants such as boiling point, melting point, density, and refractive index are not confirmed in the current source material and should be verified against the Certificate of Analysis (CoA) or the Safety Data Sheet (SDS) supplied with product SKU B120155.
Synthetic Applications and Reactivity
The aryl bromide moiety of 2-Bromo-6-fluorobenzotrifluoride is well-suited for transition-metal-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Negishi, Kumada, and Buchwald–Hartwig amination protocols. These reactions enable the introduction of aryl, heteroaryl, vinyl, amino, and other functional groups at the 2-position of the ring, generating structurally diverse fluorinated biaryl and heteroaryl products of pharmaceutical relevance.
The aryl fluoride at the 6-position is activated toward nucleophilic aromatic substitution (SNAr) by the combined electron-withdrawing effects of the adjacent trifluoromethyl group and the bromine atom. This allows selective displacement of fluorine by nitrogen, oxygen, or sulfur nucleophiles under appropriate conditions, providing access to ether, amine, or thioether derivatives without disturbing the C–Br bond when mild conditions are employed.
Researchers can thus exploit the differential reactivity of the C–Br and C–F bonds to execute sequential, orthogonal functionalization strategies, constructing complex polyfluorinated aromatic architectures from a single, readily available starting material.
Safe Handling, Storage, and Waste Disposal
As with all halogenated aromatic reagents, 2-Bromo-6-fluorobenzotrifluoride should be handled with appropriate personal protective equipment (PPE), including chemical-resistant gloves, safety goggles, and a laboratory coat. All manipulations should be conducted in a well-ventilated fume hood to minimize inhalation exposure to vapors.
The compound should be stored in tightly sealed containers in a cool, dry location, away from strong oxidizers, bases, and sources of ignition. Specific hazard classifications, GHS pictograms, first-aid measures, and exposure limits are detailed in the product Safety Data Sheet (SDS) for SKU B120155, which should be consulted before use.
Waste containing this reagent must be disposed of in accordance with local, national, and institutional regulations governing halogenated organic waste. Do not dispose of down drains or into the environment. Consult your institution's Environmental Health and Safety (EHS) office for guidance on appropriate waste streams.
Quality, Purity, and Ordering Information
Aladdin Scientific supplies 2-Bromo-6-fluorobenzotrifluoride under SKU B120155. Each lot is accompanied by a Certificate of Analysis (CoA) documenting purity, appearance, and identity confirmation by standard analytical techniques such as GC, NMR, or HPLC. Researchers are encouraged to request the CoA for the specific lot received to verify that the reagent meets the requirements of their application.
Purity grade and available pack sizes should be confirmed at the time of ordering via the Aladdin Scientific product page or by contacting the technical support team. For large-scale or custom requirements, bulk pricing inquiries can be directed to the sales department.
Proper documentation, including the SDS and CoA, should be retained for laboratory records and compliance purposes. If the received material does not meet the stated specifications, contact Aladdin Scientific's customer service team to initiate a return or replacement in accordance with the company's returns and refunds policy.
Frequently asked questions
What types of cross-coupling reactions can be performed with 2-Bromo-6-fluorobenzotrifluoride?
The aryl bromide functionality supports a broad range of palladium- and nickel-catalyzed cross-coupling reactions, including Suzuki–Miyaura (with boronic acids/esters), Negishi (with organozinc reagents), Kumada (with Grignard reagents), and Buchwald–Hartwig amination (with amines). These reactions allow diverse functionalization at the 2-position of the ring.
Can the aryl fluoride and aryl bromide be functionalized independently?
Yes. The C–Br bond is preferentially reactive under transition-metal catalysis, while the C–F bond, activated by flanking electron-withdrawing groups, can be selectively engaged in nucleophilic aromatic substitution (SNAr) under appropriate conditions. By choosing reaction conditions carefully, researchers can achieve sequential, orthogonal functionalization of each site.
How should 2-Bromo-6-fluorobenzotrifluoride be stored to maintain its integrity?
Store the reagent in a tightly sealed container in a cool, dry, and well-ventilated area, away from moisture, strong oxidizers, strong bases, and ignition sources. Consult the product SDS for SKU B120155 for specific storage temperature recommendations and shelf-life information.
Is a Certificate of Analysis available for this product?
Yes. Aladdin Scientific provides a Certificate of Analysis (CoA) with each lot of B120155, detailing purity, appearance, and identity data. Customers can request the lot-specific CoA through the product page or by contacting Aladdin Scientific customer support.
References
- Aladdin Scientific product page for 2-Bromo-6-fluorobenzotrifluoride, SKU B120155. Aladdin Scientific.
- Safety Data Sheet (SDS) for 2-Bromo-6-fluorobenzotrifluoride, SKU B120155. Aladdin Scientific. (Consult current version for hazard and handling data.)
- Ojima, I. (Ed.). Fluorine in Medicinal Chemistry and Chemical Biology. Wiley-Blackwell, 2009. (General reference for organofluorine building blocks in pharmaceutical research.)
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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