For chemical engineers, researchers, and product developers, a deep understanding of the chemical properties and synthesis of key intermediates is crucial. Biphenyldicarbonyl Chloride (CAS 2351-37-3) is a compound of significant interest due to its versatile reactivity and application in synthesizing advanced materials. This article delves into its core chemical characteristics, various synthesis methodologies, and essential handling information, providing a comprehensive overview for those looking to buy Biphenyldicarbonyl Chloride.

Chemical Profile of Biphenyldicarbonyl Chloride

Chemical Name: Biphenyldicarbonyl Chloride (also known as 4,4'-Biphenyldicarbonyl dichloride, 4,4'-Dibenzoyl chloride)

CAS Number: 2351-37-3

Molecular Formula: C14H8Cl2O2

Molecular Weight: 279.12 g/mol

Appearance: Typically a white to off-white or pale yellow powder or crystalline solid.

Key Chemical Properties:

  • Reactivity: The compound possesses two highly reactive acyl chloride (-COCl) groups. These groups are electrophilic and readily undergo nucleophilic substitution reactions with alcohols, amines, and other nucleophiles.
  • Hydrolytic Sensitivity: Biphenyldicarbonyl Chloride is sensitive to moisture. In the presence of water, it hydrolyzes to form the corresponding biphenyl-4,4'-dicarboxylic acid and hydrochloric acid. This necessitates storage and handling under anhydrous conditions.
  • Solubility: It is generally soluble in common organic solvents such as dichloromethane, chloroform, and toluene, but insoluble in water.
  • Thermal Stability: While relatively stable under dry conditions, prolonged exposure to high temperatures can lead to decomposition.

Synthesis Methodologies

The preparation of Biphenyldicarbonyl Chloride typically involves the conversion of biphenyl-4,4'-dicarboxylic acid into its corresponding diacid chloride. Several methods are employed:

  • Using Thionyl Chloride (SOCl2): This is a common and effective method where biphenyl-4,4'-dicarboxylic acid is reacted with thionyl chloride, often in the presence of a catalyst like dimethylformamide (DMF), or in an inert solvent such as toluene or dichloroethane. The byproducts (SO2 and HCl) are gaseous and easily removed.
  • Using Oxalyl Chloride ((COCl)2): Oxalyl chloride, also in combination with DMF as a catalyst, can be used for the chlorination of the dicarboxylic acid. This method is often preferred for its milder reaction conditions and the generation of gaseous byproducts (CO, CO2, HCl).
  • Using Phosphorus Oxychloride (POCl3) or Phosphorus Pentachloride (PCl5): These reagents can also be employed for the conversion of carboxylic acids to acid chlorides, though they are generally considered more aggressive and may require stricter handling precautions.

Safety and Handling Precautions

Given its reactive nature, Biphenyldicarbonyl Chloride requires careful handling:

  • Corrosive: It can cause severe skin burns and eye damage due to its reactivity and the release of HCl upon contact with moisture.
  • Irritant: Inhalation of vapors or dust can irritate the respiratory tract.
  • Handling Procedures: Always work in a well-ventilated area or fume hood. Wear appropriate personal protective equipment (PPE), including chemical-resistant gloves, safety goggles, and protective clothing. Avoid contact with skin, eyes, and clothing. Keep away from moisture and incompatible materials.

Procurement Guidance

When seeking to purchase Biphenyldicarbonyl Chloride, it is crucial to source from reputable suppliers or manufacturers in China who provide high-purity material (e.g., CAS 2351-37-3 with ≥97% purity) along with comprehensive safety data sheets (SDS) and certificates of analysis (CoA). Understanding the synthesis methods used by a supplier can also offer insights into product quality and consistency.

Conclusion

Biphenyldicarbonyl Chloride is a valuable chemical intermediate with significant utility in organic synthesis and polymer science. Its reactive nature demands careful handling, while its synthesis relies on well-established chlorination techniques. By understanding its properties and sourcing from reliable suppliers, researchers and manufacturers can effectively integrate this compound into their processes, driving innovation in chemical and material development.