3-Bromodiphenylamine: Properties, Handling & Lab Use Guide

3-Bromodiphenylamine is a brominated diarylamine building block widely employed in organic synthesis, materials science, and pharmaceutical research as a versatile intermediate for cross-coupling reactions and functional molecule construction.

Chemical Name

3-Bromodiphenylamine

Molecular Formula

C₁₂H₁₀BrN

Molecular Weight

248.12 g/mol

Functional Class

Halogenated secondary amine / aryl bromide

Primary Use

Synthetic intermediate for cross-coupling, C–N bond formation, and OLED-related materials

Aladdin SKU

B728166

Recommended Storage

Cool, dry, well-ventilated area; protect from light and moisture

Chemical Identity and Physicochemical Properties

3-Bromodiphenylamine is a secondary aromatic amine bearing a bromine substituent at the meta position of one of the two phenyl rings. Its molecular formula is C₁₂H₁₀BrN with a molecular weight of approximately 248.12 g/mol. The compound belongs to the diarylamine structural class, sharing the characteristic N–H functionality that enables further functionalization.

Key physicochemical features include moderate lipophilicity due to the two aryl rings, and the presence of both an aryl bromide (electrophilic handle) and a secondary amine (nucleophilic handle), making it a bifunctional intermediate. The compound is typically a solid at room temperature. It is sparingly soluble in water but dissolves readily in common organic solvents such as dichloromethane, tetrahydrofuran, dimethylformamide, and toluene.

Note: Precise melting point, boiling point, and density values should be confirmed from the supplier's certificate of analysis (CoA) or authoritative chemical databases such as Reaxys or SciFinder, as specific numerical data were not provided in the source material.

Laboratory Applications and Synthetic Utility

3-Bromodiphenylamine serves as a versatile bifunctional building block in synthetic organic chemistry. Its dual reactivity—an aryl bromide susceptible to oxidative addition and a secondary amine capable of nucleophilic coupling—makes it particularly valuable in the following contexts:

• Palladium-catalyzed cross-coupling reactions: The C–Br bond participates readily in Suzuki–Miyaura, Buchwald–Hartwig, and Ullmann-type coupling reactions, enabling the introduction of diverse aryl, vinyl, or heteroaryl groups at the 3-position.
• C–N bond formation: As an amine nucleophile, the N–H group can be engaged in metal-catalyzed amination reactions with aryl halides to construct triarylamine motifs, which are prominent in organic electronic materials.
• OLED and organic semiconductor materials: Triarylamines derived from diphenylamine scaffolds are well-established hole-transport materials. 3-Bromodiphenylamine provides a synthetic entry point for constructing asymmetric triarylamine derivatives useful in organic light-emitting diodes (OLEDs) and organic photovoltaics.
• Pharmaceutical and agrochemical intermediates: The diarylamine core appears in bioactive molecules; the bromo handle allows late-stage diversification via cross-coupling to explore structure–activity relationships.

Researchers are advised to optimize reaction conditions (catalyst loading, ligand, base, solvent, and temperature) based on the specific transformation targeted.

Safe Handling, Storage, and Waste Disposal

As a halogenated aromatic amine, 3-Bromodiphenylamine should be handled with appropriate caution. While a full safety data sheet (SDS) must be consulted before use, the following general guidelines apply to this class of compound:

Personal Protective Equipment (PPE): Wear nitrile or chemical-resistant gloves, a laboratory coat, and safety glasses at minimum. Use a fume hood when weighing or handling the compound to minimize inhalation of dust or vapors.

Storage: Store in a tightly sealed container in a cool, dry, and well-ventilated area, away from direct light, heat sources, strong oxidizers, and strong acids. Recommended storage temperature is typically ambient to slightly below ambient (consult CoA for specifics).

Exposure precautions: Aromatic amines as a class may present irritation risks to skin, eyes, and the respiratory tract. Avoid prolonged or repeated skin contact. In the event of skin contact, wash thoroughly with soap and water; for eye contact, rinse immediately with copious water and seek medical attention.

Waste disposal: Do not dispose of this compound via the municipal sewer system. Collect all waste—including contaminated solvents and reaction residues—in appropriately labeled containers and dispose in accordance with local, institutional, and national hazardous-waste regulations.

Important: Always refer to the current SDS supplied by Aladdin Scientific (SKU B728166) for compound-specific hazard classifications, GHS pictograms, first-aid measures, and regulatory information.

Quality, Purity, and Analytical Verification

For synthetic applications, the purity of 3-Bromodiphenylamine is critical to reaction reproducibility and yield. Researchers should consider the following quality checks upon receipt:

• Certificate of Analysis (CoA): Verify lot-specific purity, appearance, and analytical data (typically assessed by GC or HPLC) against the CoA provided by Aladdin Scientific.
• NMR Characterization: ¹H NMR in CDCl₃ or DMSO-d₆ should show the characteristic N–H proton (broad singlet), aromatic proton signals consistent with a meta-bromo substitution pattern on one ring, and the unsubstituted phenyl ring signals. ¹³C NMR and/or mass spectrometry can confirm molecular identity.
• Regiochemical confirmation: The meta (3-) regiochemistry distinguishes this compound from its 2- and 4-bromo isomers. Confirm regiochemistry via NMR coupling constants or comparison to reference spectra.
• Moisture sensitivity: Although not classified as highly moisture-sensitive, prolonged exposure to atmospheric humidity may promote gradual degradation. Verify appearance and color before use; discoloration may indicate decomposition.

Contact Aladdin Scientific technical support for lot-specific CoA documents or custom purity requirements.

Frequently asked questions

What is 3-Bromodiphenylamine primarily used for in the laboratory?

3-Bromodiphenylamine is primarily used as a bifunctional synthetic intermediate. The aryl bromide moiety participates in palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Buchwald–Hartwig), while the secondary amine can act as a nucleophile in C–N bond-forming reactions. It is especially valuable for constructing triarylamine derivatives used in OLED materials and pharmaceutical research.

How should 3-Bromodiphenylamine be stored to maintain its stability?

Store 3-Bromodiphenylamine in a tightly sealed container in a cool, dry, and well-ventilated area, away from light, heat, strong oxidizers, and strong acids. Always consult the Aladdin Scientific Certificate of Analysis (CoA) and Safety Data Sheet (SDS) for lot-specific storage temperature recommendations.

How can I confirm the regiochemistry of 3-Bromodiphenylamine versus its isomers?

The meta (3-) substitution pattern can be confirmed by ¹H NMR spectroscopy: the coupling constants and multiplicity pattern of the aromatic protons on the brominated ring (typically one doublet-like broad singlet at the 2-position relative to Br, one triplet, and one doublet) are characteristic of meta substitution. Mass spectrometry and comparison with reference spectra or the supplier's CoA provide additional confirmation.

Is 3-Bromodiphenylamine compatible with Suzuki–Miyaura coupling conditions?

Yes, the aryl C–Br bond in 3-Bromodiphenylamine is generally reactive under standard Suzuki–Miyaura coupling conditions using palladium catalysts, a boronic acid coupling partner, base, and an appropriate solvent system. However, the free N–H group may require protection or careful selection of reaction conditions to avoid side reactions or catalyst poisoning; researchers should optimize conditions empirically.

Where can I find the Safety Data Sheet (SDS) for Aladdin's 3-Bromodiphenylamine?

The SDS for 3-Bromodiphenylamine (SKU B728166) is available on the Aladdin Scientific website on the product page, or by contacting Aladdin Scientific customer service directly. Always use the current version of the SDS before handling any chemical.

References

1. Aladdin Scientific. Product Information: 3-Bromodiphenylamine, SKU B728166. Aladdin Scientific Corp.
2. Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize. Angew. Chem. Int. Ed. 2012, 51, 5062–5085. doi:10.1002/anie.201107017
3. Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C–N and C–O Bond Formation. Top. Curr. Chem. 2002, 219, 131–209. doi:10.1007/3-540-45313-X_5
4. Shirota, Y.; Kageyama, H. Charge Carrier Transporting Molecular Materials and Their Applications in Devices. Chem. Rev. 2007, 107, 953–1010. doi:10.1021/cr050143+

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