5-Bromo-2-nitrobenzotrifluoride: Handling & Application Guide

5-Bromo-2-nitrobenzotrifluoride is a versatile aromatic building block bearing both a reactive bromo leaving group and an electron-withdrawing trifluoromethyl/nitro motif, making it valuable for nucleophilic aromatic substitution, cross-coupling reactions, and the synthesis of fluorinated pharmaceutical and agrochemical intermediates.

CAS Number

367-67-9

Molecular Formula

C7H3BrF3NO2

Molecular Weight

270.00 g/mol

Appearance

Pale yellow to yellow liquid or low-melting solid

SKU

B120168

Primary Functional Groups

Aryl bromide, nitro group, trifluoromethyl group

Storage Recommendation

Store in a cool, dry, well-ventilated area away from light and moisture

Chemical Identity and Properties

5-Bromo-2-nitrobenzotrifluoride (CAS 367-67-9; SKU B120168) is also known as 2-nitro-4-bromobenzotrifluoride or 4-bromo-3-nitrobenzotrifluoride depending on numbering convention. Its molecular formula is C₇H₃BrF₃NO₂ with a molecular weight of approximately 270.00 g/mol.

The molecule features three electron-withdrawing substituents on the benzene ring: a trifluoromethyl (–CF₃) group, a nitro (–NO₂) group, and a bromo (–Br) substituent. The combined inductive and resonance effects of the –CF₃ and –NO₂ groups strongly activate the ring toward nucleophilic aromatic substitution (S_NAr) at positions bearing the halide. The compound is typically a pale yellow to light yellow liquid or low-melting solid at ambient temperature.

Key physicochemical parameters should be confirmed against the Certificate of Analysis (CoA) supplied with each lot. Purity is typically verified by GC or HPLC; researchers should request the CoA from Aladdin Scientific for lot-specific data.

Synthetic Applications and Reaction Protocols

Nucleophilic Aromatic Substitution (S_NAr): The electron-deficient aromatic ring, activated by both ortho/para –NO₂ and –CF₃ groups, undergoes efficient displacement of the bromide by nitrogen-, oxygen-, and sulfur-centered nucleophiles. Typical conditions employ a polar aprotic solvent (DMF, DMSO, or NMP) with an inorganic base (K₂CO₃, Cs₂CO₃) at 60–120 °C. Reaction progress should be monitored by TLC or HPLC.

Palladium-Catalyzed Cross-Coupling: The C–Br bond participates in standard Suzuki–Miyaura, Buchwald–Hartwig, and Negishi coupling reactions. Typical Suzuki conditions use Pd(PPh₃)₄ or Pd(dppf)Cl₂ as catalyst (1–5 mol%), arylboronic acid partner, K₂CO₃ or Na₂CO₃ base, and a toluene/ethanol/water solvent mixture at 80–100 °C under inert atmosphere.

Nitro Group Reduction: The –NO₂ group can be selectively reduced to an aniline using Fe/AcOH, Zn/NH₄Cl, or catalytic hydrogenation (H₂/Pd-C), providing access to 5-bromo-2-aminobenzotrifluoride derivatives for further elaboration.

General Protocol Tips: Ensure all glassware is oven-dried and reactions are performed under inert atmosphere (N₂ or Ar) when using sensitive metal catalysts. Record the exact mass of reagent dispensed; the compound may absorb trace moisture on prolonged storage after opening.

Safety, Handling, and Storage Guidelines

Hazard Classification: 5-Bromo-2-nitrobenzotrifluoride is an irritant and should be treated as a potentially harmful compound. It may cause skin, eye, and respiratory tract irritation. Researchers must consult the Safety Data Sheet (SDS) supplied by Aladdin Scientific before use.

Personal Protective Equipment (PPE): Wear chemical-resistant gloves (nitrile or neoprene), safety goggles, and a laboratory coat. Handle in a fume hood to avoid inhalation of vapors or dust. A half-face respirator with organic vapor cartridge is recommended if ventilation is inadequate.

First Aid: In case of skin contact, wash immediately with soap and water for at least 15 minutes. For eye contact, rinse with copious water for at least 15 minutes and seek medical attention. If inhaled, move to fresh air and seek medical advice.

Storage: Store in a tightly sealed container in a cool (2–25 °C), dry, well-ventilated area, away from direct light, heat sources, and incompatible materials (strong oxidizers, strong bases). Segregate from food and feed. Shelf life and specific storage temperature should be confirmed on the product label and CoA.

Waste Disposal: Dispose of waste in accordance with local, national, and institutional regulations for halogenated organic waste. Do not pour down the drain.

Quality, Purity, and Ordering Information

Product SKU: B120168 (5-Bromo-2-nitrobenzotrifluoride) is available from Aladdin Scientific. Contact your regional Aladdin representative or visit the Aladdin Scientific website for current pack sizes, pricing, and availability.

Purity Specification: Lot-specific purity data are provided in the Certificate of Analysis (CoA). Researchers requiring high-purity material for sensitive assays should confirm the purity grade (typically ≥97% or ≥98% GC) prior to ordering. Request CoA documentation at the time of purchase.

Packaging: Available in various pack sizes suitable for discovery-scale synthesis through multi-gram preparative work. Packaging is designed to minimize moisture ingress and protect against light degradation during transit and storage.

Regulatory and Export: No special export license is typically required for this compound, but researchers should verify applicable local regulations. This product is intended for research and development use only and is not for human, veterinary, or food use.

Frequently asked questions

What reactions is 5-Bromo-2-nitrobenzotrifluoride most commonly used for?

It is most frequently employed in nucleophilic aromatic substitution (SNAr) reactions due to the strong electron-withdrawing activation provided by the ortho-nitro and trifluoromethyl groups. It also serves as an aryl bromide partner in palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura and Buchwald–Hartwig couplings, and as a precursor for fluorinated aniline intermediates via nitro group reduction.

How should 5-Bromo-2-nitrobenzotrifluoride be stored to maintain stability?

The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated area, away from direct light and heat sources. Temperatures between 2 and 25 °C are generally appropriate, but researchers should confirm recommended conditions on the product label and Certificate of Analysis. Once opened, minimize exposure to atmospheric moisture.

Is 5-Bromo-2-nitrobenzotrifluoride available in different purity grades or pack sizes?

Aladdin Scientific offers this compound (SKU B120168) in various pack sizes to accommodate different research needs, from small-scale exploratory synthesis to larger preparative quantities. Lot-specific purity data are documented in the Certificate of Analysis. Contact Aladdin Scientific or visit the website for current specifications and availability.

What personal protective equipment is required when handling this compound?

Researchers should wear chemical-resistant gloves (nitrile or neoprene), safety goggles, and a laboratory coat. All handling should be performed in a fume hood. If adequate ventilation cannot be ensured, a half-face respirator with an organic vapor cartridge is recommended. Always consult the SDS for complete safety guidance.

References

1. Aladdin Scientific Product Page and Certificate of Analysis for 5-Bromo-2-nitrobenzotrifluoride, SKU B120168.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 4th ed. Wiley-Interscience, 1992. (General reference for SNAr and cross-coupling reaction conditions.)
3. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chemical Reviews, 1995, 95(7), 2457–2483. doi:10.1021/cr00039a007

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