4,4'-Diaminodiphenylsulfone
[CAS# 80-08-0]

Identification

• Classification: API >> Synthetic anti-infective drugs >> Anti-tuberculosis leprosy
• Name: 4,4'-Diaminodiphenylsulfone
• Synonyms: 4,4'-Diaminodiphenyl sulfone; Dapsonum; Bis(4-aminophenyl)sulfone
• Molecular Formula: C₁₂H₁₂N₂O₂S
• Molecular Weight: 248.30
• CAS Registry Number: 80-08-0
• EC Number: 201-248-4
• SMILES: C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)N

Properties

• Density: 1.4$+/-$0.1 g/cm³ Calc.^*
• Melting point: 175 - 177 $degree$C (Expl.)
• Boiling point: 511.7$+/-$35.0 $degree$C 760 mmHg (Calc.)^*
• Flash point: 263.2$+/-$25.9 $degree$C (Calc.)^*
• Solubility: DMSO:10Mm, water: $lessThan$0.1 g/100 mL (20 $degree$C) (Expl.)
• Index of refraction: 1.662 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Specific target organ toxicity - single exposure	STOT SE	2	H371
Reproductive toxicity	Repr.	1B	H360F
Acute toxicity	Acute Tox.	3	H301
Specific target organ toxicity - repeated exposure	STOT RE	1	H372

Discovery and Applications

4,4'-Diaminodiphenylsulfone is an aromatic diamine compound consisting of two benzene rings linked by a sulfone (–SO₂–) group, with each ring substituted by a primary amino group at the para (4-) position relative to the sulfone linkage. This arrangement combines nucleophilic amino groups with a highly electron-withdrawing and thermally stable sulfone bridge, making it an important monomer in high-performance polymer chemistry.

The molecular structure features a central sulfone group connecting two para-amino-substituted benzene rings. The sulfone linkage provides rigidity, chemical resistance, and high thermal stability, while the amino groups serve as reactive sites for condensation reactions with various diacid, dianhydride, or epoxide compounds. This combination of functional groups allows the synthesis of polymers with exceptional mechanical properties, heat resistance, and chemical durability.

Synthesis of 4,4'-diaminodiphenylsulfone generally involves the reaction of 4-nitrochlorobenzene with sodium sulfinate to introduce the sulfone linkage, followed by reduction of nitro groups to amino groups. High-purity products are obtained to ensure effective polymerization and consistent material performance. Alternative routes include direct sulfonation of aromatic amines under controlled conditions to achieve the desired substitution pattern.

One of the primary applications of 4,4'-diaminodiphenylsulfone is in the production of polyethersulfones, polyimides, and epoxy resins. Polymers derived from this diamine exhibit high thermal stability, excellent mechanical strength, and resistance to chemical degradation, making them suitable for aerospace, electronics, and automotive applications. These materials are used in coatings, adhesives, insulating films, and composite structures that require stability under extreme conditions.

In addition to polymer synthesis, 4,4'-diaminodiphenylsulfone serves as a building block for dyes, pigments, and specialty chemicals. Its amino groups enable functionalization, while the sulfone core ensures rigidity and thermal resistance, allowing the design of compounds for high-performance applications.

Overall, 4,4'-diaminodiphenylsulfone is a chemically versatile and thermally robust aromatic diamine. Its combination of nucleophilic amino groups and a sulfone bridge makes it a critical intermediate for producing high-performance polymers, functional materials, and specialty chemical derivatives.

References

2025. [Divided bullae: half-half blisters in IgA pemphigus]. Dermatologie (Heidelberg, Germany).
DOI: 10.1007/s00105-025-05548-3

2025. [Treatment of oral lichen planus-a review]. Dermatologie (Heidelberg, Germany).
DOI: 10.1007/s00105-025-05540-x

2025. Design, synthesis and biological evaluation of dapsone derivatives with broad-spectrum antiviral activity. European Journal of Medicinal Chemistry.
DOI: 10.1016/j.ejmech.2025.117717