Chemical Identity and Structure

1-(5-Bromo-2-nitrophenyl)pyrrolidine (SKU B178903) is an N-arylpyrrolidine in which the pyrrolidine nitrogen is bonded to a phenyl ring bearing a bromine substituent at the 5-position and a nitro group at the 2-position (ortho to nitrogen). The molecular formula is C₁₀H₁₁BrN₂O₂, giving a molecular weight of approximately 271.11 g/mol.

The ortho-nitro group exerts a strong electron-withdrawing inductive and resonance effect on the aromatic ring. Combined with the electron-donating pyrrolidine ring, this compound presents a push-pull electronic architecture that influences both its reactivity and its spectroscopic properties. The aryl bromide at the 5-position serves as a handle for further functionalization via palladium-catalyzed cross-coupling reactions or nucleophilic aromatic substitution (SNAr) when additional activation is present.

Key identifiers:

• SKU: B178903
• Molecular formula: C₁₀H₁₁BrN₂O₂
• Molecular weight: ~271.11 g/mol
• Functional groups: aryl bromide, nitro, tertiary cyclic amine

Synthetic Applications and Reactivity

1-(5-Bromo-2-nitrophenyl)pyrrolidine is employed primarily as a multifunctional building block in the synthesis of bioactive molecules. Its reactivity profile is governed by three distinct sites:

1. Aryl bromide (C–Br bond): Undergoes palladium-catalyzed cross-coupling reactions including Suzuki–Miyaura, Buchwald–Hartwig, and Sonogashira couplings, enabling introduction of aryl, heteroaryl, amino, or alkynyl groups at the 5-position.
2. Nitro group: Can be selectively reduced to the corresponding aniline using standard reducing agents (e.g., iron/acetic acid, hydrogen/Pd-C, or tin(II) chloride). The resulting aniline is a versatile handle for further elaboration, including amide bond formation, reductive amination, and cyclization.
3. Pyrrolidine ring: The tertiary amine nitrogen stabilizes the compound toward electrophilic aromatic attack at the ring and may influence biological activity when this scaffold is incorporated into drug candidates.

This compound is particularly useful in medicinal chemistry programs targeting kinase inhibitors, GPCR modulators, and other therapeutic areas where diarylamine and ortho-substituted aniline motifs are prevalent. Researchers should note that the combination of aryl bromide and nitro group within the same molecule allows sequential, orthogonal functionalization strategies.

Handling, Safety, and Storage Guidelines

As with all nitroaromatic and organobromine laboratory reagents, appropriate precautions must be observed when handling 1-(5-Bromo-2-nitrophenyl)pyrrolidine. The following guidelines reflect general best practice for compounds of this class; consult the product-specific Safety Data Sheet (SDS) for authoritative hazard data before use.

Personal Protective Equipment (PPE)

• Wear chemical-splash safety goggles or face shield.
• Use nitrile or neoprene gloves; inspect for integrity before each use.
• Don a laboratory coat or chemical-resistant apron.
• Work in a well-ventilated fume hood to minimize inhalation exposure to dust or vapors.

Storage

• Store in a tightly sealed container in a cool (below 25 °C), dry, well-ventilated location.
• Keep away from heat, open flames, and ignition sources.
• Segregate from strong oxidizing agents, strong acids, and strong bases.
• Label containers clearly with compound name, SKU (B178903), and date received.

Spill and Disposal

• Contain small spills with inert absorbent material (e.g., vermiculite, dry sand); avoid generating dust.
• Dispose of waste in accordance with local, national, and institutional regulations for halogenated aromatic waste streams.
• Do not pour down the drain or discharge to the environment.

Quality, Purity, and Analytical Characterization

Aladdin Scientific provides 1-(5-Bromo-2-nitrophenyl)pyrrolidine (SKU B178903) as a research-grade reagent. Researchers should verify suitability for their specific application by reviewing the Certificate of Analysis (CoA) available on the product page.

Typical Analytical Methods for Identity and Purity Confirmation

• HPLC or GC: Used to assess chromatographic purity. For sensitive synthetic applications, a purity of ≥95% is generally recommended.
• NMR Spectroscopy (¹H and ¹³C): Confirms regiochemistry and structural integrity. Characteristic signals include aromatic protons in the 7–8 ppm region, pyrrolidine methylene protons around 1.8–3.5 ppm, and absence of N–H signals consistent with a tertiary amine.
• Mass Spectrometry (MS): Confirms molecular ion at m/z ~271/273 (characteristic bromine isotope pattern, M and M+2 in ~1:1 ratio).
• Melting Point: Can be used as a physical identity check; consult the CoA for specification.

If the compound is to be used in biological assays, researchers should confirm the absence of cytotoxic impurities and verify solubility in the intended assay vehicle (e.g., DMSO, ethanol, or aqueous buffer). Stock solutions in anhydrous DMSO are commonly employed; prepare fresh dilutions to avoid hydrolysis or decomposition over extended storage.