What Is 2-Amino-4'-chlorobiphenyl?

2-Amino-4'-chlorobiphenyl (CAS 3114-17-8) is a halogenated biphenyl derivative carrying a primary amino group at the 2-position of one phenyl ring and a chlorine atom at the 4'-position of the second phenyl ring. The compound belongs to the broader class of aromatic amines and polychlorinated biphenyl-related structures. Its bifunctional nature — combining a nucleophilic amine handle with an electrophilic aryl-chloride site — makes it attractive as a synthetic building block for the preparation of more complex heterocyclic or biaryl frameworks used in pharmaceutical discovery and advanced materials research.

Key Chemical and Physical Properties

The molecular formula of 2-Amino-4'-chlorobiphenyl is C₁₂H₁₀ClN with a molecular weight of approximately 203.67 g/mol. As a solid aromatic amine, it is typically a pale crystalline material at room temperature. Like most biphenyl derivatives, it is sparingly soluble in water but dissolves readily in common organic solvents such as dichloromethane, ethyl acetate, dimethylformamide (DMF), and dimethyl sulfoxide (DMSO). The presence of the electron-withdrawing chlorine on the remote ring and the electron-donating amino group on the other ring creates an asymmetric electronic landscape that influences its reactivity in coupling reactions, diazotization, and acylation chemistry.

Note: Precise melting point, boiling point, and purity specification values should be confirmed against the current Aladdin certificate of analysis (CoA) for lot C302612.

Synthesis and Research Applications

2-Amino-4'-chlorobiphenyl serves as a versatile precursor in several synthetic contexts:

• Suzuki–Miyaura and Buchwald–Hartwig couplings: The aryl chloride moiety can participate in palladium-catalyzed cross-coupling reactions to introduce additional aryl or heteroaryl groups, while the amine may be protected or left free depending on the reaction design.
• Diazotization chemistry: The primary amine can be converted to a diazonium salt under standard conditions, enabling access to azo dyes, biaryl halides via Sandmeyer reaction, or phenols via hydrolysis.
• Heterocycle synthesis: Ortho-aminobiphenyl scaffolds are classical precursors to carbazoles, acridines, and related N-containing polycyclic systems relevant to OLED materials and kinase inhibitor programs.
• Medicinal chemistry SAR studies: The compound is used to explore structure–activity relationships (SAR) in programs targeting a range of biological receptors, where the 4'-chloro substitution modulates lipophilicity and binding affinity.

Safe Handling, Storage, and Disposal

Hazard awareness: 2-Amino-4'-chlorobiphenyl is an aromatic amine. As a chemical class, aromatic amines are associated with potential mutagenic and carcinogenic risk; this specific compound should be treated as a potential hazard until definitive toxicological data are available. Always consult the current Safety Data Sheet (SDS) before use.

Personal protective equipment (PPE): Wear appropriate gloves (nitrile recommended), eye protection, and a lab coat. Handle in a well-ventilated fume hood. Avoid inhalation of dust or vapors.

Storage: Store in a tightly sealed container in a cool, dry, well-ventilated area away from oxidizing agents, strong acids, and light. Refrigerated storage (2–8 °C) is typically recommended for long-term stability of aromatic amine reagents.

Disposal: Dispose of as hazardous chemical waste in accordance with local, national, and institutional regulations. Do not pour down the drain.

Ordering and Quality Information

2-Amino-4'-chlorobiphenyl is available from Aladdin Scientific under SKU C302612. Each lot is accompanied by a Certificate of Analysis (CoA) documenting purity, appearance, and analytical data. Researchers requiring high-purity material for sensitive applications such as asymmetric catalysis or reference standard work should request the CoA prior to ordering to confirm the specific lot meets their specifications.

For bulk quantities, custom packaging, or questions about lead times, please contact Aladdin Scientific customer service. Orders can be placed through the Aladdin online store, and reward points and promotional pricing may apply — refer to current promotions on the website for details.