Chemical Identity and Properties

1-(Benzyloxy)-4-bromo-2-(trifluoromethyl)benzene (SKU B181997) is a trisubstituted benzene derivative bearing three distinct functional handles: an aryl bromide at the 4-position, a benzyloxy (OBn) protecting group at the 1-position, and an electron-withdrawing trifluoromethyl (CF3) group at the 2-position. Its molecular formula is C14H10BrF3O with a molecular weight of approximately 331.13 g/mol.

The CF3 group confers strong electron-withdrawing character on the aromatic ring, activating the ring toward nucleophilic aromatic substitution (SNAr) at appropriate positions while simultaneously influencing the reactivity of the aryl bromide in metal-catalyzed transformations. The benzyloxy moiety serves as a masked phenol, readily removable by hydrogenolysis under mild palladium-on-carbon/H2 conditions. These combined features make this compound an exceptionally versatile intermediate for multi-step synthetic sequences.

The compound is expected to be a colorless to pale yellow liquid or low-melting solid at ambient temperature. It should be stored in a tightly sealed container, protected from light and moisture, at 2–8 °C or as specified on the product label.

Handling, Safety, and Storage Guidelines

Personal Protective Equipment (PPE): Always wear appropriate PPE when handling this compound, including nitrile gloves, a laboratory coat, and safety glasses or a face shield. Work in a well-ventilated fume hood to minimize inhalation of vapors or aerosols.

Skin and Eye Contact: Avoid direct skin and eye contact. In case of contact, flush immediately with copious amounts of water for at least 15 minutes and seek medical attention if irritation persists. The aryl bromide and CF3-containing compound may be irritating to skin, eyes, and mucous membranes.

Storage: Store in a cool, dry, well-ventilated area away from direct sunlight and incompatible materials (strong oxidizing agents, strong bases). Keep container tightly closed between uses. Recommended storage temperature is 2–8 °C for long-term stability.

Disposal: Dispose of waste material in accordance with applicable local, regional, and national regulations for halogenated organic waste. Do not pour down drains or into the environment.

Spill Response: In case of a spill, contain the material using inert absorbent (e.g., vermiculite or dry sand), collect in a sealed waste container, and decontaminate the affected area with appropriate solvent followed by soap and water.

Note: Always consult the Safety Data Sheet (SDS) for this product before use. The SDS contains detailed hazard information, first-aid measures, and regulatory data specific to this compound.

Synthetic Applications and Reaction Protocols

1-(Benzyloxy)-4-bromo-2-(trifluoromethyl)benzene serves as a multifunctional building block exploitable through three principal reaction strategies:

1. Palladium-Catalyzed Cross-Coupling Reactions: The aryl bromide at the 4-position is well-suited for a range of Pd(0)/Pd(II)-catalyzed transformations including Suzuki–Miyaura cross-coupling (with aryl- or alkenylboronic acids/esters), Buchwald–Hartwig amination (with primary or secondary amines), Negishi coupling (with organozinc reagents), and Heck reactions. Standard Suzuki conditions (e.g., Pd(PPh3)4 or Pd(dppf)Cl2, K2CO3, toluene/ethanol/water, 80–90 °C) are expected to be applicable. The electron-withdrawing CF3 group generally facilitates oxidative addition of Pd(0) into the C–Br bond.

2. Nucleophilic Aromatic Substitution (SNAr): The combination of the ortho-CF3 group and the para-bromo substituent creates a sufficiently electron-deficient ring to potentially participate in SNAr reactions with suitable nucleophiles such as amines, alkoxides, or thiols, depending on the specific substitution pattern and reaction conditions.

3. Benzyloxy Deprotection to Reveal the Phenol: The benzyloxy group can be cleanly removed by catalytic hydrogenolysis (Pd/C, H2, EtOH or MeOH, room temperature) or by transfer hydrogenation (Pd/C, ammonium formate), unmasking the corresponding 4-bromo-2-(trifluoromethyl)phenol for further functionalization.

Recommended practice: Conduct all metal-catalyzed reactions under an inert atmosphere (N2 or Ar) using degassed solvents. Purify products by column chromatography on silica gel using appropriate hexane/ethyl acetate gradients.

Quality, Purity, and Analytical Characterization

Aladdin Scientific supplies 1-(Benzyloxy)-4-bromo-2-(trifluoromethyl)benzene (SKU B181997) to research-grade purity standards. Users requiring specific purity data should consult the Certificate of Analysis (CoA) provided with each lot.

Recommended Analytical Methods:

• 1H NMR and 19F NMR: NMR spectroscopy is the primary tool for structural confirmation and purity assessment. The 19F NMR spectrum should display a characteristic singlet for the CF3 group (typically around −60 to −63 ppm relative to CFCl3). The 1H NMR spectrum should show signals consistent with the benzyloxy CH2 protons (~5.2 ppm, s, 2H), phenyl protons of the benzyl group (~7.3–7.5 ppm), and aromatic protons of the substituted ring.
• GC or HPLC Purity: Gas chromatography (GC) with FID detection or reversed-phase HPLC (C18 column, acetonitrile/water gradient) can be used to quantify chemical purity and detect trace impurities.
• Mass Spectrometry: EI-MS or ESI-MS should confirm the molecular ion consistent with C14H10BrF3O (M+ ~330/332, characteristic bromine isotope pattern).
• Melting Point / Boiling Point: Physical property measurements serve as additional identity checks; refer to the CoA for lot-specific values.

If the compound appears discolored or has changed physical form upon receipt, contact Aladdin Scientific customer service and retain the original packaging for quality review.

Ordering, Storage Conditions, and Customer Support

How to Order: 1-(Benzyloxy)-4-bromo-2-(trifluoromethyl)benzene is available from Aladdin Scientific under SKU B181997. Place orders through the Aladdin Scientific website, by contacting your regional sales representative, or via your institutional procurement system. Bulk quantities may be available upon request; please contact customer service for pricing and lead times.

Shipping and Storage Upon Receipt: The compound is typically shipped at ambient temperature. Upon receipt, transfer to cold storage (2–8 °C) in a sealed, clearly labeled container away from light. Check the lot-specific CoA to confirm purity and identity before committing the material to a synthesis campaign.

Returns and Quality Issues: If you receive material that does not meet specification, contact Aladdin Scientific customer service within the timeframe specified in the returns policy. Provide the order number, lot number, and a description of the quality concern. Aladdin Scientific will initiate a replacement or refund process in accordance with its standard returns and refunds policy.

Technical Support: For questions about the suitability of this compound for a specific application, reaction optimization, or reagent compatibility, reach out to the Aladdin Scientific technical team via the website or customer service channels.