3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone Chemical Properties

Melting point:

231 °C

Boiling point:

596.9±50.0 °C(Predicted)

Density 

1.564±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

slightly sol. in Methanol

form 

powder to crystal

pka

6.62±0.20(Predicted)

color 

White to Gray to Brown

InChI

InChI=1S/C12H12N2O4S/c13-9-5-7(1-3-11(9)15)19(17,18)8-2-4-12(16)10(14)6-8/h1-6,15-16H,13-14H2

InChIKey

KECOIASOKMSRFT-UHFFFAOYSA-N

SMILES

S(C1=CC=C(O)C(N)=C1)(C1=CC=C(O)C(N)=C1)(=O)=O

CAS DataBase Reference

7545-50-8(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

HazardClass 

IRRITANT

HS Code 

29222990

3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone Usage And Synthesis

Description

3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone is a kind of fragrant heterocyclic monomer that can be used as the monomer preparing polybenzoxazoles (PBO) speciality polymer functional materials. There are under high temperatures with outstanding mechanical and dielectric properties, except for outstanding thermostability. Also, there is outstanding fibre and film performance, widely used in the aerospace cause, the textile industry and other needs to strengthen the field of resistance to heat.

Chemical Properties

3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone is a white to grey to brown powder to crystal with a melting point of 231 °C, slightly soluble in methanol.

Uses

3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone is an organic reagent mainly used in chemical and experimental research. 3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone and its derivatives can be used in the preparation of a permanently fixing film, an anodic photosensitive resin precursor compositions and moulding compositions containing polyimide components. In addition, 3,3'-diallyl-4,4'-dihydroxydiphenyl sulfone (DA-DHDPS) can be used to prepare fast photocrosslinkable polyethersulfone coatings^[1].

Synthesis

The general procedure for the synthesis of bis(3-amino-4-hydroxyphenyl)sulfone from 3,3'-dinitro-4,4'-dihydroxydiphenylsulfone was as follows: 3.4 kg of 3,3'-dinitro-4,4'-dihydroxydiphenylsulfone, 9.5 kg of dimethylsulfoxide (DMSO), and 3.18 kg of aqueous 5.3% ammonium chloride were added to a reactor, and the temperature was slowly raised to 50°C. Subsequently, 2.5 kg of reduced iron powder was added in batches (material molar ratio of 3,3'-dinitro-4,4'-dihydroxydiphenylsulfone: iron: chlorinated iron). 2.5 kg of reduced iron powder was added in batches (material molar ratio of 3,3'-dinitro-4,4'-dihydroxydiphenylsulfone: iron: ammonium chloride: water: DMSO = 1:4.5:6:29:12). After completion of the reaction, hot filtration was performed and the filter cake was washed with hot DMSO. The filtrates were combined and evaporated under reduced pressure to give a mixed solution of DMSO and water, which was cooled to 5°C to promote precipitation of the product. After stopping the distillation, the solid product was collected by filtration, washed with water and dried to give 2.6 kg of 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone in 93% yield.

References

[1] Z. ZENG. Photosensitive poly(ether sulfone)s for thiol/ene UV curable coatings: synthesis, characterization and crosslinking[J]. e-Polymers, 2010. DOI:10.1515/epoly.2010.10.1.1013.

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