1-Bromo-2-chloro-4,5-difluorobenzene: Properties & Lab Use FAQ
1-Bromo-2-chloro-4,5-difluorobenzene: Properties & Lab Use FAQ
1-Bromo-2-chloro-4,5-difluorobenzene is a polyhalogenated aromatic building block widely used in medicinal chemistry, agrochemical research, and materials science as a versatile intermediate for cross-coupling and nucleophilic aromatic substitution reactions.
- Chemical Name
- 1-Bromo-2-chloro-4,5-difluorobenzene
- SKU
- B700705
- Molecular Formula
- C₆H₂BrClF₂
- Molecular Weight
- 227.43 g/mol
- Halogen Substituents
- Bromo, chloro, and two fluoro groups on a benzene ring
- Primary Applications
- Cross-coupling reactions, nucleophilic aromatic substitution, pharmaceutical and agrochemical intermediates
What Is 1-Bromo-2-chloro-4,5-difluorobenzene?
1-Bromo-2-chloro-4,5-difluorobenzene (SKU: B700705) is a polyfluorinated, polyhalogenated benzene derivative bearing four different or identical halogen substituents at defined ring positions. Its molecular formula is C₆H₂BrClF₂ with a molecular weight of approximately 227.43 g/mol. The compound belongs to the class of aryl halides and serves as a versatile electrophilic aromatic building block. The presence of electron-withdrawing fluorine atoms at the 4- and 5-positions activates the ring toward nucleophilic aromatic substitution (SNAr), while the C–Br bond provides a preferred site for transition-metal-catalysed cross-coupling reactions such as Suzuki–Miyaura, Negishi, and Buchwald–Hartwig couplings. The C–Cl bond offers an additional handle for orthogonal functionalisation under more forcing conditions or with appropriate catalysts.
Key Chemical Properties and Handling
As a liquid or low-melting solid aromatic halide, 1-Bromo-2-chloro-4,5-difluorobenzene should be stored in a tightly sealed container, away from strong bases and reducing agents, under cool and dry conditions. Standard laboratory personal protective equipment (PPE) — including chemical-resistant gloves, safety goggles, and a laboratory coat — should be worn when handling this material. Work should be conducted in a well-ventilated fume hood, as halogenated aromatic compounds may cause irritation upon inhalation or skin contact. Consult the Safety Data Sheet (SDS) supplied with Aladdin product B700705 for full hazard classifications, first-aid measures, and disposal guidance in accordance with local regulations.
The compound is relatively stable under ambient conditions but should be protected from prolonged exposure to moisture and light to prevent slow decomposition. Long-term storage is best maintained at 2–8 °C or as specified on the product label.
Synthetic Applications and Reaction Selectivity
The orthogonal reactivity of the C–Br, C–Cl, and C–F bonds in 1-Bromo-2-chloro-4,5-difluorobenzene makes it an exceptionally useful building block for multi-step synthesis. In general, reactivity toward palladium-catalysed cross-coupling follows the order C–Br > C–Cl >> C–F, allowing selective mono-functionalisation at the bromo position under standard Suzuki or Negishi conditions. Subsequent activation of the C–Cl bond can be achieved with more active catalyst systems or under higher temperatures.
The fluorine atoms at the 4- and 5-positions activate adjacent positions toward SNAr with nitrogen, oxygen, or sulfur nucleophiles, particularly when the reaction is assisted by additional electron-withdrawing substituents. This dual reactivity profile is exploited in the synthesis of pharmaceutically relevant heterocycles, fluorinated biaryl scaffolds, and advanced intermediates for agrochemical programmes.
Purity, Quality, and Ordering Information
Aladdin Scientific offers 1-Bromo-2-chloro-4,5-difluorobenzene under SKU B700705. Researchers should confirm the purity grade and specification on the current product page or request a Certificate of Analysis (CoA) prior to use, particularly for sensitive applications such as pharmaceutical intermediate synthesis where impurity profiles can affect downstream reactions. Aladdin's quality control processes include identity verification by NMR or GC-MS and purity assessment by GC. For bulk quantities or custom purity requirements, contact Aladdin's sales team directly.
Frequently asked questions
What cross-coupling reactions can 1-Bromo-2-chloro-4,5-difluorobenzene participate in?
The C–Br bond of 1-Bromo-2-chloro-4,5-difluorobenzene preferentially undergoes palladium-catalysed cross-coupling reactions, including Suzuki–Miyaura (with boronic acids), Negishi (with organozinc reagents), and Buchwald–Hartwig (C–N bond formation) couplings under standard conditions. The C–Cl bond can be engaged under more forcing conditions or with highly active catalyst systems, enabling sequential, orthogonal functionalisation.
How should I store 1-Bromo-2-chloro-4,5-difluorobenzene to maintain its stability?
Store 1-Bromo-2-chloro-4,5-difluorobenzene in a tightly sealed container in a cool, dry, well-ventilated area, away from moisture, direct light, strong bases, and reducing agents. Long-term storage at 2–8 °C is recommended, or follow the specific storage conditions stated on the Aladdin product label and Certificate of Analysis for SKU B700705.
Can the fluorine atoms in 1-Bromo-2-chloro-4,5-difluorobenzene be selectively displaced by nucleophiles?
Yes. The fluorine atoms at the 4- and 5-positions activate the ring toward nucleophilic aromatic substitution (SNAr) due to their strong electron-withdrawing inductive effect. Heteroatom nucleophiles such as amines, alkoxides, or thiolates can displace one or both fluorines under appropriate conditions, particularly when additional electron-withdrawing groups are present to further stabilise the Meisenheimer complex intermediate.
What safety precautions should I follow when using 1-Bromo-2-chloro-4,5-difluorobenzene in the lab?
Always handle 1-Bromo-2-chloro-4,5-difluorobenzene in a well-ventilated fume hood while wearing appropriate PPE, including chemical-resistant gloves, safety goggles, and a laboratory coat. Avoid inhalation and skin or eye contact. Refer to the Safety Data Sheet (SDS) for product B700705 available from Aladdin Scientific for full hazard information, first-aid procedures, and waste disposal guidelines compliant with local regulations.
How do I confirm the identity and purity of 1-Bromo-2-chloro-4,5-difluorobenzene upon receipt?
Request the Certificate of Analysis (CoA) for lot B700705 from Aladdin Scientific, which documents identity confirmation (typically by NMR or GC-MS) and purity data (typically by GC). For critical applications, in-house verification by ¹H NMR, ¹⁹F NMR, or GC analysis is recommended to confirm the compound meets your experimental requirements before use.
References
- Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; Wiley-VCH: New York, 1999. (General reference for aryl halide reactivity and cross-coupling reactions.)
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (Textbook-level discussion of nucleophilic aromatic substitution and SNAr mechanisms.)
- Aladdin Scientific. Product Page: 1-Bromo-2-chloro-4,5-difluorobenzene, SKU B700705. https://www.aladdin-e.com (accessed 2024).
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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