4,4'-Oxybisbenzoyl chloride
[CAS# 7158-32-9]

Identification

• Classification: Organic raw materials >> Aryl compounds
• Name: 4,4'-Oxybisbenzoyl chloride
• Synonyms: 4,4'-Oxydibenzoyl chloride; 4-(Chlorocarbonyl)phenyl ether; Diphenyl ether 4,4'-dicarbonyl dichloride; Diphenyl oxide 4,4'-dicarbonyl chloride
• Molecular Formula: C₁₄H₈Cl₂O₃
• Molecular Weight: 295.12
• CAS Registry Number: 7158-32-9
• EC Number: 808-159-5
• SMILES: C1=CC(=CC=C1C(=O)Cl)OC2=CC=C(C=C2)C(=O)Cl

Properties

• Density: 1.386
• Melting point: 22-23 °C
• Boiling point: 404 °C
• Flash point: 164 °C

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H314-H318
• Safety Statements: P260-P264-P264+P265-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1A	H314
Skin corrosion	Skin Corr.	1B	H314
Substances or mixtures corrosive to metals	Met. Corr.	1	H290

• Transport Information: UN 3261

Discovery and Applications

4,4'-Oxybisbenzoyl chloride, with the chemical formula C₁₄H₈Cl₂O₃, is a versatile compound known for its use in organic synthesis. It belongs to the class of acyl chlorides characterized by two benzoyl chloride groups connected by an ether bridge. The discovery of 4,4'-Oxybisbenzoyl chloride stems from the need for compounds that can act as efficient acylating agents in organic chemistry. Researchers have focused on developing molecules with stable acyl chloride functional groups connected by a rigid ether bridge. The discovery of this compound involves synthetic methods that achieve high purity and high yield, suitable for industrial-scale applications.

The synthesis of 4,4'-Oxybisbenzoyl chloride generally involves the reaction of benzoyl chloride with a suitable ether precursor under controlled conditions, which reacts with an ether linker such as benzyl ether or bisphenol A to form an ether bridge between the two benzoyl chloride groups. The resulting intermediate is chlorinated to replace the hydroxyl group with a chlorine atom to give 4,4'-Oxybisbenzoyl chloride.

4,4'-Oxybisbenzoyl chloride is widely used in polymer chemistry as a monomer for the synthesis of high-performance polymers. It is a key component in the production of liquid crystal polymers (LCPs) and other specialty polymers with excellent thermal and mechanical properties.

In the textile industry, 4,4'-Oxybisbenzoyl chloride is used as a crosslinking agent for the manufacture of flame-retardant fabrics and fibers. It is able to form strong covalent bonds with cellulose and synthetic fibers, thereby enhancing the durability and flame retardancy of the fabric.

In pharmaceutical chemistry, this compound is useful as an intermediate for the synthesis of bioactive compounds and pharmaceutical ingredients. It participates in acylation reactions to modify the molecular structure and enhance pharmacological properties.

Historically, 4,4'-Oxybisbenzoyl chloride has been used in the photographic industry to manufacture photosensitive materials and emulsions. Its acyl chloride functionality enables chemical modifications that optimize photosensitive properties and image quality.

Due to its acyl chloride nature, 4,4'-Oxybisbenzoyl chloride requires careful handling and storage to prevent exposure to moisture and ensure stability. Safety procedures should be followed to minimize the risks associated with its corrosive properties and skin and respiratory irritation.

References

2020. Synthesis of 4,4′-Oxydibenzoic Acid Amides and Sulfonamides Containing 2-Arylaminopyrimidine Moieties. Russian Journal of Organic Chemistry, 56(12).
DOI: 10.1134/s1070428020120076

2017. Synthesis of comb-shaped polymers via controlled cationic polymerization of oxazolines with polyester-type macroinitiator. Polymer Science, Series B, 59(2).
DOI: 10.1134/s156009041702004x

2000. Thermal conversion of t -butyloxycarbonyloxy attached polyamides to polybenzoxazoles. Polymer Bulletin, 44(2).
DOI: 10.1007/s002890050573