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4-Bromofluorobenzene (C₆H₄BrF, CAS 460-00-4) is a para-disubstituted benzene derivative with bromine and fluorine on opposite ring positions.
Key Points:
Reactivity:
Bromine serves as a leaving group in cross-coupling reactions (e.g., Suzuki, Stille).
Fluorine is activated for nucleophilic substitution (SNAr) due to the para-bromine's electron-withdrawing effect.
Uses: A versatile building block in synthesizing pharmaceuticals, agrochemicals, and liquid crystals.
Properties: Colorless/pale-yellow liquid (m.p. ≈ −16°C, b.p. ≈ 152°C); insoluble in water.
Safety: Toxic, irritant, and environmentally hazardous.
Distinction: Unlike its ortho isomer, the para position eliminates steric effects, enhancing SNAr reactivity.
In short: A key para-halogenated synthon for coupling and SNAr chemistry.
4-Bromofluorobenzene (C₆H₄BrF) is an aromatic compound where a benzene ring is substituted with bromine (Br) and fluorine (F) at para positions (opposite sides). Key details:
Formula: C₆H₄BrF
CAS No.: 460-00-4
Appearance: Colorless to pale-yellow liquid or low-melting solid (m.p. ~-16°C, b.p. ~152°C).
Structure:
F
│
◻─◻
│ │
◻─◻─Br
Electrophile: Bromine acts as a leaving group in cross-coupling reactions (e.g., Suzuki, Stille).
Nucleophilic Substitution (SNAr): Fluorine is highly activated for SNAr by the para-bromine (e.g., reacts with amines, alkoxides).
Building Block: Used to synthesize pharmaceuticals, agrochemicals, and liquid crystals.
Electronic Effects: Bromine (+R effect) and fluorine (-I effect) balance ring electronics.
Toxic if ingested/inhaled, irritant, and environmentally hazardous. Handle with PPE.
Key Distinction vs. Ortho-Isomer: The para position eliminates steric effects, enhancing SNAr reactivity at fluorine and simplifying coupling reactions at bromine.
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