369462

4-Aminophenyl disulfide

98%

• Synonym(s): 4,4′-Dithiodianiline
• Linear Formula: (H₂NC₆H₄S-)₂
• CAS Number: 722-27-0
• Molecular Weight: 248.37
• NACRES: NA.23
• PubChem Substance ID: 24862976
• UNSPSC Code: 12162002
• EC Number: 211-961-2
• MDL number: MFCD00007882

Properties

• Quality Segment: 100
• assay: 98%
• form: powder
• mp: 77-78 °C (lit.)
• SMILES string: Nc1ccc(SSc2ccc(N)cc2)cc1
• InChI: 1S/C12H12N2S2/c13-9-1-5-11(6-2-9)15-16-12-7-3-10(14)4-8-12/h1-8H,13-14H2
• InChI key: MERLDGDYUMSLAY-UHFFFAOYSA-N

Description

General description

4-Aminophenyl disulfide is primarily used as a reagent in chemical synthesis. It has thiol-disulfide interchange properties, making it useful in redox reactions and the synthesis of polymers. It can participate in thiol-disulfide exchange reactions, facilitating the formation of covalent bonds with other thiols or disulfides. 4-Aminophenyl disulfide is often employed as a crosslinking agent, particularly in polymerization reactions, where it can enhance the mechanical and thermal properties of polymers. It can also act as a dopant or charge-transfer agent in conductive polymers, improving their electrical conductivity.

Application

4-Aminophenyl disulfide can be used as:

• A crosslinker in the synthesis of self-healing poly(urea-urethane) elastomers because of its quantitative healing efficiency. These self-healing materials find applications in various fields such as drug delivery, wound healing, and tissue engineering, electronics, aerospace, and coatings.
• A hardener in the formulation of re-processable, repairable, and recyclable epoxy networks due to the presence of dynamic disulfide bonds, which enable the epoxy networks to undergo chemical recycling. These epoxy networks are widely used in various applications which include, composite materials, coatings, adhesives, and fiber-reinforced thermoset composites.
• A crosslinking agent for the development of epoxy vitrimers and carbon fiber composites with enhanced mechanical properties, multi-shape memory capabilities for the potential applications in high-performance materials.

4-Aminophenyl disulfide can also be used in the following:
Bioconjugation: The amine group can react with carboxylic acids or their derivatives, making it useful for conjugating biomolecules like proteins and peptides. This is particularly valuable in developing targeted drug delivery systems where the drug is directly linked to a molecule that can home in on cancer cells or other disease sites.
Diagnostic Agents: It can be used to modify surfaces of diagnostic devices, such as biosensors. They can help in the immobilization of biomolecules on sensor surfaces, improving the sensitivity and specificity of detection.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves