3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone
[CAS# 7545-50-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Sulfone, sulfoxide compound
• Name: 3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone
• Synonyms: 4,4'-Sulfonylbis(2-aminophenol); 3-Amino-4-hydroxyphenyl sulfone; 2-Amino-4-[(3-amino-4-hydroxybenzene)sulfonyl]phenol
• Molecular Formula: C₁₂H₁₂N₂O₄S
• Molecular Weight: 280.30
• CAS Registry Number: 7545-50-8
• EC Number: 231-428-8
• SMILES: C1=CC(=C(C=C1S(=O)(=O)C2=CC(=C(C=C2)O)N)N)O

Properties

• Density: 1.6$+/-$0.1 g/cm³ Calc.^*
• Boiling point: 596.9$+/-$50.0 $degree$C 760 mmHg (Calc.)^*
• Flash point: 314.8$+/-$30.1 $degree$C (Calc.)^*
• Index of refraction: 1.717 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317-H319
• Safety Statements: P261-P264+P265-P272-P280-P302+P352-P305+P351+P338-P321-P333+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone is an aromatic diamine compound in which two benzene rings are linked by a sulfone (–SO₂–) group, with each ring bearing an amino group at the 3-position and a hydroxyl group at the 4-position. This molecular arrangement combines nucleophilic amino functionalities with hydroxyl groups and a highly electron-withdrawing sulfone bridge, making the compound valuable as an intermediate in polymer chemistry and materials science. The combination of reactive amino and hydroxyl groups allows for multiple condensation and crosslinking reactions, while the sulfone group imparts thermal stability and chemical resistance to derived materials.

The molecular structure consists of a central sulfone connecting two para-hydroxylated and meta-amino-substituted benzene rings. The amino groups serve as nucleophilic centers that can participate in polycondensation reactions with dianhydrides, diacids, or epoxides to form polyamides, polyimides, and epoxy resins. The hydroxyl groups can undergo etherification, esterification, or further crosslinking, providing versatility in polymer design. The sulfone bridge introduces rigidity and polarity into the molecule, enhancing thermal and oxidative stability in resulting polymers.

Synthesis of 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone generally starts from bisphenol precursors or sulfonation reactions of appropriately substituted aromatic compounds, followed by nitration and subsequent reduction of nitro groups to yield the diamine. Reaction conditions are carefully controlled to avoid over-nitration or oxidation of the hydroxyl groups, and purification is performed to obtain high-purity intermediates suitable for polymerization.

One of the primary applications of this compound is in high-performance polymer production. Its bifunctional nature allows it to serve as a monomer for polyethersulfones, polyimides, and epoxy resins with excellent thermal, chemical, and mechanical properties. Polymers derived from this diamine are used in electronics, aerospace, membranes for gas separation, coatings, adhesives, and composite materials where stability at high temperatures and chemical resistance are critical.

In addition to polymer applications, 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone is used as an intermediate in the synthesis of dyes, pigments, and functionalized aromatic derivatives. Its amino and hydroxyl groups allow for selective chemical transformations, enabling the preparation of molecules with tailored properties for industrial or research purposes.

Overall, 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone is a versatile aromatic diamine with hydroxyl functionality and a sulfone bridge that provide chemical reactivity, structural rigidity, and thermal stability. Its combination of nucleophilic sites and electron-withdrawing linkage makes it a critical intermediate in the production of high-performance polymers, functional materials, and specialty chemical derivatives.

References

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DOI: 10.1016/j.bbrc.2023.08.050

2022. A quantitative high-throughput screen identifies compounds that lower expression of the SCA2-and ALS-associated gene ATXN2. The Journal of biological chemistry.
DOI: 10.1016/j.jbc.2022.102228

2022. Discovery of small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase. Journal of Enzyme Inhibition and Medicinal Chemistry.
DOI: 10.1080/14756366.2022.2070909