5397-34-2

Basic information

• Product Name: 2,4'-DIHYDROXYDIPHENYL SULFONE
• Synonyms: 2-((4-hydroxyphenyl)sulfonyl)-pheno;2-((4-hydroxyphenyl)sulfonyl)phenol;2,4’-Dihydroxydiphenylsulfon;2,4’-sulfonyldi-pheno;2,4’-sulfonyldiphenol;2-[(4-hydroxyphenyl)sulfonyl]-pheno;4,2’-dihydroxydiphenylsulfone;o,p-dihydroxydiphenylsulfone
• CAS NO: 5397-34-2
• Molecular Formula: C₁₂H₁₀O₄S
• Molecular Weight: 250.27
• EINECS: 226-421-1
• Mol File: 5397-34-2.mol
• Article Data: 14

Chemical Properties

• Melting Point: 184°C
• Boiling Point: 487.2 °C at 760 mmHg
• Flash Point: 248.5 °C
• Appearance: /
• Density: 1.432 g/cm³
• Vapor Pressure: 4.06E-10mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 7.09±0.15(Predicted)
• CAS DataBase Reference: 2,4'-DIHYDROXYDIPHENYL SULFONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4'-DIHYDROXYDIPHENYL SULFONE(5397-34-2)
• EPA Substance Registry System: 2,4'-DIHYDROXYDIPHENYL SULFONE(5397-34-2)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RTECS: SL5365000
• Hazardous Substances Data: 5397-34-2(Hazardous Substances Data)

Usage

Uses

24 Bisphenol S is a material used in thermal printing. 24 Bisphenol S is also used in the development of black leuco dyes.

InChI:InChI=1/C12H10O4S/c13-9-5-7-10(8-6-9)17(15,16)12-4-2-1-3-11(12)14/h1-8,13-14H

Synthetic route

phenol (108-95-2) → 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
Stage #1: phenol With sulfuric acid; benzene-1,3-disulfonic acid In 1,3,5-trimethyl-benzene at 145 - 165℃; for 5h; Heating / reflux; Stage #2: at 170 - 185℃; under 525.053 Torr; for 2h; Product distribution / selectivity;	A 94% B n/a
With sulfuric acid In 1,3,5-trimethyl-benzene at 145 - 165℃; for 5h; Product distribution / selectivity; Heating / reflux;	A 89% B n/a
Stage #1: phenol With sulfuric acid In 1,3,5-trimethyl-benzene at 145 - 165℃; for 5h; Heating / reflux; Stage #2: at 170 - 185℃; under 525.053 Torr; for 2h; Product distribution / selectivity;	A 83% B n/a

1-chloro-2-(4-chlorophenylsulfonyl)benzene (38980-51-7) → 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
With potassium hydroxide at 160 - 165℃;
With potassium hydroxide at 160 - 165℃;

1-methoxy-2-((4-methoxyphenyl)sulfonyl)benzene (24197-29-3) → 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
With aluminium trichloride; xylene

sulfuric acid (7664-93-9) + phenol (108-95-2) → 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
at 165 - 200℃;

sulfuric acid (7664-93-9) + sulfur trioxide (7446-11-9) + phenol (108-95-2) → 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
at 180 - 190℃;

4-Methoxybenzenethiol (696-63-9) → 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: copper-powder / 235 - 240 °C 2: KMnO4; glacial acetic acid / Erwaermen auf dem Dampfbad 3: AlCl3; xylene View Scheme

monosodium salt of 2,4'-dihydroxydiphenylsulfone (202924-57-0) → 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
With sulfuric acid In water
With sulfuric acid In methanol

fluorosulphonic acid (HFSO3) + phenol (108-95-2) → 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
With hydrogen fluoride

4,4'-dichlorodiphenyl sulphone (80-07-9) + 1-chloro-2-(4-chlorophenylsulfonyl)benzene (38980-51-7) → 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
With water; sodium hydroxide at 220℃; for 4h;

chlorobenzene (108-90-7) → 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
Stage #1: chlorobenzene With sulfur trioxide; dimethyl sulfate at 30℃; for 2h; Stage #2: With sodium hydroxide In water at 220℃; for 4h;

trifluoromethylsulfonic anhydride (358-23-6) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2) → 2,4'-bis(trifluoromethylsulfonyloxy)diphenylsulfone (1228364-92-8)

Conditions	Yield
Stage #1: 2,4'-dihydroxydiphenyl sulfone With pyridine In dichloromethane at -78℃; for 0.166667h; Inert atmosphere; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at -78 - 0℃; Inert atmosphere;	81%

2,4'-dihydroxydiphenyl sulfone (5397-34-2) → (2-benzoyloxy-phenyl)-(4-benzoyloxy-phenyl)-sulfone

2,4'-dihydroxydiphenyl sulfone (5397-34-2) + acetyl chloride (75-36-5) → (2-acetoxy-phenyl)-(4-acetoxy-phenyl)-sulfone (57154-52-6)

Conditions	Yield
With acetic acid

2,4'-dihydroxydiphenyl sulfone (5397-34-2) + dimethyl sulfate (77-78-1) → 1-methoxy-2-((4-methoxyphenyl)sulfonyl)benzene (24197-29-3)

Conditions	Yield
With alkaline solution

N,N-bis-(2-chloroethyl)carbamoyl chloride (2998-56-3) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2) → 2,4'-Bisdiphenylsulfon (6526-89-2)

Conditions	Yield
With pyridine

Upstream product

• 529-28-2 4-iodoanisol 
• 108-95-2 phenol 
• 108-90-7 chlorobenzene 
• 14065-23-7 1-methoxy-2-[(4-methoxyphenyl)thio]benzene 
• 7217-59-6 2-Methoxybenzenethiol 
• 696-62-8 para-iodoanisole 
• 696-63-9 4-Methoxybenzenethiol 
• 7664-93-9 sulfuric acid 
• 7446-11-9 sulfur trioxide 
• 24197-29-3 1-methoxy-2-((4-methoxyphenyl)sulfonyl)benzene 
• 38980-51-7 1-chloro-2-(4-chlorophenylsulfonyl)benzene 
• 80-07-9 4,4'-dichlorodiphenyl sulphone 
• 202924-57-0 monosodium salt of 2,4'-dihydroxydiphenylsulfone 

Downstream Products

• 6526-89-2 2,4'-Bisdiphenylsulfon 
• 24197-29-3 1-methoxy-2-((4-methoxyphenyl)sulfonyl)benzene 
• 57154-52-6 (2-acetoxy-phenyl)-(4-acetoxy-phenyl)-sulfone 

Relevant articles and documents

Separation of 2,4′- and 4,4′-dihydroxydiphenyl sulfones

To develop a procedure for separating 2,4′- and 4,4′- dihydroxydiphenyl sulfones, their acidity and solubility in water were studied. Pleiades Publishing, Inc., 2006.

Liquid-crystal aromatic polyesters containing azo and sulfone units

Two novel aromatic polyesters containing azo and sulfone units were synthesized by poly-condensation of 4,4′-azobenzene-dicarbonyl chloride with dihydroxydiphenyl sulfones at low temperature. The synthesized polymers exhibited good solubility, inherent viscosity (reaches 1.05 dL g-1), high glass transition temperature (above 200 °C) and thermal stability (≤ 5 % weight loss at 348 °C), which were characterized by Fourier transform infrared spectroscopy. The liquid crystalline and photoisomerization properties were observed by polarizing optical microscope and an ultraviolet-visible spectrophotometer.

PROCESS FOR THE PRODUCTION OF A SULFONE MONOMER

The present invention provides an economic and environmentally friendly method for the preparation of polymer grade 4,4'-dichlorodiphenyl sulfone which is substantially free of 2,4' and 3,4'-isomers of dichlorodiphenyl sulfone with yield of over 90%, with substantially reduced reaction times without the use of impregnated catalysts. Further no toxic byproducts such as dimethyl pyrosulfate are formed thereby reducing the load on effluent treatment with the added advantage of substantially recycling the reactants and byproducts. Further the present invention discloses a process is disclosed in which isomeric mixture of 4,4'-, 3,4'-, and 2,4'-dichlorodiphenyl sulfone produced during the preparation of 4,4'-dichlorodiphenyl sulfone is converted to value added products such as diphenyl sulfone, 2,4'- dihydroxydiphenyl sulfone, 4,4'-dihydroxydiphenyl sulfone and 2-aminodiphenyl sulfone.