2664-63-3

Basic information

• Product Name: 4,4'-Thiobis-phenol
• Synonyms: 4-Hydroxyphenyl sulfide, TDP;4,4'-Thiodbisphenol;fine cheMical interMediate;interMediate coMpound;pharMaceutical interMediate;4,4'-Dihydroxydiphenyl Sulfide 4,4'-Thiodiphenol;4,4'-Thiobis-phenol 4-Hydroxyphenyl sulfide;BIS(4-HYDROXYPHENYL)SULFIDE FOR SYNTHESI
• CAS NO: 2664-63-3
• Molecular Formula: C₁₂H₁₀O₂S
• Molecular Weight: 218.27
• EINECS: 220-197-9
• Product Categories: Biochemistry;Color Former & Related Compounds;Developer;Diphenyl Sulfides (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;Reagents for Oligosaccharide Synthesis;intermediate compound;chemical additive;fine chemical intermediate;pharmaceutical intermediate;pharmaceutical intermediates
• Mol File: 2664-63-3.mol
• Article Data: 42

Chemical Properties

• Melting Point: 154-156 °C(lit.)
• Boiling Point: 328.96°C (rough estimate)
• Flash Point: 219.7 °C
• Appearance: White to pale brown/Crystalline Powder
• Density: 1.2618 (rough estimate)
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: 9.31±0.26(Predicted)
• Water Solubility: Insoluble in water
• Sensitive: Air Sensitive
• BRN: 2050739
• CAS DataBase Reference: 4,4'-Thiobis-phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Thiobis-phenol(2664-63-3)
• EPA Substance Registry System: 4,4'-Thiobis-phenol(2664-63-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 2
• RTECS: SN0800000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 2664-63-3(Hazardous Substances Data)

Usage

Chemical Properties

White, crystalline powder.

Uses

Different sources of media describe the Uses of 2664-63-3 differently. You can refer to the following data:
1. Intermediate, flame-retardant, antioxidant, engineering plastics.
2. 4,4'-thiobis-phenol can be applied to produce a non-halogen type epoxy (meth)acrylate resin having high refractive index, transparency and thermal stability. It is also used to produce a non-systemic organophosphorus insecticide TEMEPHOS.

Synthetic route

bis(4-hydroxyphenyl) sulfoxide (1774-34-1) → 4,4'-Thiodiphenol (2664-63-3)

Conditions	Yield
With phosphorus trichloride In acetonitrile at 25℃; for 0.5h; Schlenk technique;	94%
With phosphorus trichloride In acetonitrile at 25℃; for 0.5h; Schlenk technique;	94%
With silica bromide In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere;	91%

phenol (108-95-2) → 4,4'-Thiodiphenol (2664-63-3)

Conditions	Yield
With tetraethylammonium perchlorate In acetonitrile for 2h; Ambient temperature; working pot.: 2.2 V vs SCE;	92%
With N,N'-thiodimorpholine; boron trifluoride In dichloromethane at -78 - 25℃;	46%
With carbon disulfide; sulfur dichloride

4-Iodophenol (540-38-5) → 4,4'-Thiodiphenol (2664-63-3)

Conditions	Yield
With sulfur; sodium hydroxide In dimethyl sulfoxide at 130℃; for 3.33333h;	90%
With sulfur; potassium hydroxide In dimethyl sulfoxide at 130℃; for 1.66667h; Green chemistry;	88%
With potassium hydroxide In dimethyl sulfoxide at 120℃; for 3h; Green chemistry;	74%
With thiourea; potassium hydroxide In dimethyl sulfoxide at 130℃; for 6h; Reagent/catalyst;	67%

4-bromo-phenol (106-41-2) → 4,4'-Thiodiphenol (2664-63-3)

Conditions	Yield
With sulfur; potassium hydroxide In dimethyl sulfoxide at 130℃; for 2.16667h; Green chemistry;	88%
With sulfur; potassium hydroxide In dimethyl sulfoxide at 110℃; for 1.16667h;	83%
With sulfur; sodium hydroxide In dimethyl sulfoxide at 130℃; for 4.33333h;	73%

4-sulfanylphenol (637-89-8) + (p-hydroxyphenyl)boronic acid (71597-85-8) → 4,4'-Thiodiphenol (2664-63-3)

Conditions	Yield
Stage #1: 4-sulfanylphenol With [2,2]bipyridinyl; nickel(II) chloride hexahydrate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.0833333h; Stage #2: (p-hydroxyphenyl)boronic acid With potassium tert-butylate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 12h; chemoselective reaction;	81%

4-chloro-phenol (106-48-9) → 4,4'-Thiodiphenol (2664-63-3)

Conditions	Yield
With sulfur; potassium hydroxide In neat (no solvent) at 110℃; for 7.3h; Reagent/catalyst; Green chemistry; chemoselective reaction;	68%
With sulfur; potassium hydroxide In dimethyl sulfoxide at 100℃; for 12h;	55%
With thiourea; potassium hydroxide at 100℃; for 3.5h; Catalytic behavior;	55%
With thiourea; sodium hydroxide In dimethyl sulfoxide at 130℃; for 10.5h;	43%

phenol (108-95-2) → 4,4'-Thiodiphenol (2664-63-3) + (2-hydroxyphenyl 4-hydroxyphenyl)sulfure (17755-37-2)

Conditions	Yield
With tetraethylammonium perchlorate; trichloroacetic acid In dichloromethane for 2h; Ambient temperature; working pot.: 2.2 V vs SCE;	A 48% B 37%

4-bromo-phenol (106-41-2) → ortho-mercaptophenol (1121-24-0) + 2,4-dibromophenol (615-58-7) + 2-hydroxybromobenzene (95-56-7) + 4,4'-Thiodiphenol (2664-63-3) + phenol (108-95-2)

Conditions	Yield
With hydrogen sulfide; sulfur at 110℃; for 3h; Mechanism; Product distribution; var. temp. and time; other halogenophenols, also phenol;	A 5.1% B 8.5% C 9.6% D n/a E 32.6%

p-diazophenol (19089-85-1) → bis(4-hydroxyphenyl)disulfide (15015-57-3) + 4,4'-Thiodiphenol (2664-63-3)

Conditions	Yield
With sodium hydroxide; sodium disulfide at 90℃;

4,4'-thiobisaniline (139-65-1) → 4,4'-Thiodiphenol (2664-63-3)

Conditions	Yield
With sulfuric acid; acetic acid; isopentyl nitrite Diazotization.Eintragen der erhaltenen Diazoniumsalz-Loesung in wss. H2SO4 bei Siedetemperatur;

tris-(4-hydroxy-phenyl)-sulfonium ; chloride (17755-35-0) → 4,4'-Thiodiphenol (2664-63-3) + phenol (108-95-2)

Conditions	Yield
at 260℃;

bis(4-hydroxyphenyl) sulfoxide (1774-34-1) + phenol (108-95-2) → 4,4'-Thiodiphenol (2664-63-3)

Conditions	Yield
With hydrogenchloride; chloroform

tris(4-tert-butoxycarbonyloxyphenyl)sulfonium trifluoromethylsulphonate → 4,4'-Thiodiphenol (2664-63-3) + tris(4-hydroxyphenyl)sulphonium (88101-75-1) + C22H26O6S (138888-97-8) + (4-tert-Butoxycarbonyloxy-phenyl)-bis-(4-hydroxy-phenyl)-sulfonium (138888-96-7) + Bis-(4-tert-butoxycarbonyloxy-phenyl)-(4-hydroxy-phenyl)-sulfonium (127175-63-7)

Conditions	Yield
In water; acetonitrile Product distribution; Quantum yield; Mechanism; Ambient temperature; Irradiation; other solvent;

tris(4-tert-butoxycarbonyloxyphenyl)sulfonium trifluoromethylsulphonate → 4,4'-Thiodiphenol (2664-63-3) + tris(4-hydroxyphenyl)sulphonium (88101-75-1) + (4-tert-Butoxycarbonyloxy-phenyl)-bis-(4-hydroxy-phenyl)-sulfonium (138888-96-7) + Bis-(4-tert-butoxycarbonyloxy-phenyl)-(4-hydroxy-phenyl)-sulfonium (127175-63-7)

Conditions	Yield
In acetonitrile Product distribution; Quantum yield; Mechanism; Ambient temperature; Irradiation; without water, other solvents;

tris(4-tert-butoxycarbonyloxyphenyl)sulfonium hexafluoroarsenate → 4,4'-Thiodiphenol (2664-63-3) + tris(4-hydroxyphenyl)sulphonium (88101-75-1) + (4-tert-Butoxycarbonyloxy-phenyl)-bis-(4-hydroxy-phenyl)-sulfonium (138888-96-7) + Bis-(4-tert-butoxycarbonyloxy-phenyl)-(4-hydroxy-phenyl)-sulfonium (127175-63-7)

Conditions	Yield
In acetonitrile Product distribution; Quantum yield; Mechanism; Ambient temperature; Irradiation; without water, other solvents;

4-chloro-phenol (106-48-9) → 4-sulfanylphenol (637-89-8) + 4,4'-Thiodiphenol (2664-63-3) + phenol (108-95-2)

Conditions	Yield
With ethanethiol at 540℃; for 0.0138889h; Product distribution; other reagents (hydrogensulfid), yield calculated on reacted comp.;	A 31.2 % Chromat. B 7.0 % Chromat. C 50.0 % Chromat.
With hydrogen sulfide at 540℃; for 0.00833333h; Mechanism;	A 27.5 % Turnov. B 9.2 % Turnov. C 52.0 % Turnov.

thionyl chloride (7719-09-7) + phenol (108-95-2) → 4,4'-Thiodiphenol (2664-63-3)

phenol (108-95-2) + chlorosulfur + CS2 → 4,4'-Thiodiphenol (2664-63-3)

Conditions	Yield
unter Kuehlung;

thionyl chloride (7719-09-7) + chloroform (67-66-3) + phenol (108-95-2) → 4,4'-Thiodiphenol (2664-63-3) + 4-chloro-phenol (106-48-9) + tris-<4-hydroxy-phenyl>-sulfonium-chloride

sulfate 4.4'-diamino-diphenyl sulfide → 4,4'-Thiodiphenol (2664-63-3)

Conditions	Yield
Diazotization.man zersetzt das Diazoniumsulfat mit Wasser;

tris-<4-hydroxy-phenyl>-sulfonium-chloride → 4,4'-Thiodiphenol (2664-63-3)

Conditions	Yield
at 260℃;

chloroform (67-66-3) + bis(4-hydroxyphenyl) sulfoxide (1774-34-1) + hydrogen bromide (10035-10-6, 12258-64-9) + phenol (108-95-2) → 4-bromo-phenol (106-41-2) + 4,4'-Thiodiphenol (2664-63-3)

hydrogenchloride (7647-01-0) + chloroform (67-66-3) + bis(4-hydroxyphenyl) sulfoxide (1774-34-1) + phenol (108-95-2) → 4,4'-Thiodiphenol (2664-63-3) + 4-chloro-phenol (106-48-9) + tris-<4-hydroxy-phenyl>-sulfonium-chloride

water (7732-18-5) + tris-(4-hydroxy-phenyl)-sulfonium ; chloride (17755-35-0) → 4,4'-Thiodiphenol (2664-63-3)

Conditions	Yield
at 160℃;

aniline (62-53-3) → 4,4'-Thiodiphenol (2664-63-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: lead (II)-oxide; sulfur / 135 - 145 °C 2: glacial acetic acid; concentrated sulfuric acid; isopentyl nitrite / Diazotization.Eintragen der erhaltenen Diazoniumsalz-Loesung in wss. H2SO4 bei Siedetemperatur View Scheme

4,4-dihydroxydiphenyl sulphide + phenol (108-95-2) → 4,4'-Thiodiphenol (2664-63-3)

4-Iodophenol (540-38-5) → bis(4-hydroxyphenyl)disulfide (15015-57-3) + 4,4'-Thiodiphenol (2664-63-3)

Conditions	Yield
With sulfur; copper(l) iodide; lithium hydroxide monohydrate In N,N-dimethyl-formamide at 100℃; for 168h; Inert atmosphere;	A 11 %Spectr. B 89 %Spectr.

phenol (108-95-2) → 4,4'-Thiodiphenol (2664-63-3) + 4-chloro-phenol (106-48-9)

Conditions	Yield
With aluminum (III) chloride; thionyl chloride In diethyl ether at 25℃;	A 91 %Chromat. B 9 %Chromat.

Ni(2+)*2C6H5OS(1-) → 4,4'-Thiodiphenol (2664-63-3) + nickel monosulfide + phenol (108-95-2)

Conditions	Yield
at 500℃; for 1h; Inert atmosphere; Sealed tube;

4,4'-Thiodiphenol (2664-63-3) → bis(4-hydroxyphenyl) sulfoxide (1774-34-1)

Conditions	Yield
With dihydrogen peroxide In acetonitrile at 25℃; for 4h; Catalytic behavior; Green chemistry; chemoselective reaction;	100%
With dihydrogen peroxide In neat (no solvent) at 20℃; for 0.166667h; Green chemistry; chemoselective reaction;	97%
With 3-chloro-benzenecarboperoxoic acid In methanol; dichloromethane for 1h;	95%

trifluoromethylsulfonic anhydride (358-23-6) + 4,4'-Thiodiphenol (2664-63-3) → 4,4'-thiodiphenyl bistriflate

Conditions	Yield
Stage #1: 4,4'-Thiodiphenol With pyridine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 0℃; Inert atmosphere;	99.2%

4,4'-Thiodiphenol (2664-63-3) + tert-butyldimethylsilyl chloride (18162-48-6) → (4,4'-thiobis(4,1-phenylene)bis(oxy))bis(tert-butyldimethylsilane)

Conditions	Yield
With 1H-imidazole; dmap In dichloromethane; N,N-dimethyl-formamide for 3h;	99%
With 1H-imidazole In dichloromethane at 20℃;	90%

4,4'-Thiodiphenol (2664-63-3) → 4,4'-thiobis(4,1-phenylene) disulfofluoridate

Conditions	Yield
With fluorosulfonyl fluoride; triethylamine In dichloromethane at 20℃; for 12h;	98%

4,4'-Thiodiphenol (2664-63-3) + bis(diethylamino)phenylphosphine (1636-14-2) → N,N,N',N'-tetraethyl-4,4'-thiodiphenylenebis(amidophenylphosphonite)

Conditions	Yield
at 120 - 125℃; for 2.8h; phosphorylation;	97%

4,4'-Thiodiphenol (2664-63-3) → 2,2'-dihydroxydiphenyl sulfoxide (32568-76-6)

Conditions	Yield
With dihydrogen peroxide In water; acetic acid	97%

4,4'-Thiodiphenol (2664-63-3) → 4,4'-sulfonediphenol (80-09-1)

Conditions	Yield
With dihydrogen peroxide In water at 20℃; for 0.833333h; chemoselective reaction;	94%
With dihydrogen peroxide In methanol at 40℃; for 0.666667h; chemoselective reaction;	90%
With palladium; dihydrogen peroxide In methanol at 100℃; for 12h; Green chemistry; chemoselective reaction;	87%

4,4'-Thiodiphenol (2664-63-3) → C12H8O2S(2-)*2Na(1+)

Conditions	Yield
With sodium hydroxide In cyclohexanone at 100℃; for 4h;	94%

formaldehyd (50-00-0) + 3-aminopropyltriethoxysilane (919-30-2) + 4,4'-Thiodiphenol (2664-63-3) → C34H56N2O8SSi2

Conditions	Yield
In 1,4-dioxane at 95℃; for 6h;	93.2%

4,4'-Thiodiphenol (2664-63-3) + benzyl bromide (100-39-0) → bis(4-(benzyloxy)phenyl)sulfane (98985-98-9)

Conditions	Yield
Stage #1: 4,4'-Thiodiphenol With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: benzyl bromide In tetrahydrofuran at 20℃;	93%

meta-dinitrobenzene (99-65-0) + 4,4'-Thiodiphenol (2664-63-3) → 4,4'-bis(3-nitrophenoxy)diphenyl sulfide (105112-85-4)

Conditions	Yield
With potassium carbonate In methanol; N,N-dimethyl-formamide	92.3%

4,4'-Thiodiphenol (2664-63-3) + pyridine-3-carbonyl chloride hydrochloride (20260-53-1) → bis(nicotinoyl)-4,4'-thiodiphenolate (941571-87-5)

Conditions	Yield
With pyridine In chloroform at 20℃; for 3h;	92%

4-(chlorocarbonyl)pyridine (14254-57-0) + 4,4'-Thiodiphenol (2664-63-3) → bis[(4-isonicotinoyloxy)phenyl]sulfide (1107604-48-7)

Conditions	Yield
With pyridine In chloroform at 0 - 20℃;	92%

4,4'-Thiodiphenol (2664-63-3) + benzyl chloride (100-44-7) → bis(4-(benzyloxy)phenyl)sulfane (98985-98-9)

Conditions	Yield
Stage #1: 4,4'-Thiodiphenol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Inert atmosphere; Stage #2: benzyl chloride In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;	91%

4,4'-Thiodiphenol (2664-63-3) + propargyl bromide (106-96-7) → C18H14O2S

Conditions	Yield
With potassium hydroxide In acetone for 16h; Heating;	90%

4,4'-Thiodiphenol (2664-63-3) + 2-bromoethanol (540-51-2) → 2,2'-((thiobis(4,1-phenylene))bis(oxy))bis(ethan-1-ol) (29802-09-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 24h;	87%

4,4'-Thiodiphenol (2664-63-3) + 3-quinuclidinol (1619-34-7) → 4-{[4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenyl]thio}phenol (854934-91-1)

Conditions	Yield
	86%

2-chloro-5-nitropyridine (4548-45-2) + 4,4'-Thiodiphenol (2664-63-3) → 4,4'-bis(5-nitro-2-pyridinoxy)diphenyl thioether

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 70℃; Inert atmosphere;	86%

4,4'-Thiodiphenol (2664-63-3) + cyanomethyl bromide (590-17-0) → 2,2'-((thiobis(4,1-phenylene))bis(oxy))diacetonitrile

Conditions	Yield
Stage #1: 4,4'-Thiodiphenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: cyanomethyl bromide In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;	83%

4,4'-Thiodiphenol (2664-63-3) + allyl bromide (106-95-6) → 4,4'-thiodiphenol diallyl ether (99873-56-0)

Conditions	Yield
With sodium hydroxide; tetramethylammonium bromide In toluene at 49.9 - 59.9℃; for 20h;	80%

4-Nitrophthalonitrile (31643-49-9) + 4,4'-Thiodiphenol (2664-63-3) → C28H14N4O2S

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 5h;	80%
With potassium carbonate In N,N-dimethyl-formamide at 20 - 85℃; for 5h;	80%

4,4'-Thiodiphenol (2664-63-3) + tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate (145013-05-4) → 1,3-di(tert-butoxycarbonyl)-2-[4-(4-hydroxyphenylsulfanyl)phenyl]isourea (1073524-90-9) + 4,4'-bis[N,N'-di(tert-butoxycarbonyl)isoureido]diphenyl thioether (1073524-86-3)

Conditions	Yield
With triethylamine; mercury dichloride In dichloromethane at 0 - 20℃; for 17h;	A 78% B 5%
With triethylamine; mercury dichloride In dichloromethane at 0 - 20℃; for 22h;	A 20% B 61%

4,4'-Thiodiphenol (2664-63-3) + hexadecanyl bromide (112-82-3) → 4-((4-(hexadecyloxy)phenyl)thio)phenol

Conditions	Yield
With potassium carbonate In ethanol at 90℃; for 24h;	78%

4,4'-Thiodiphenol (2664-63-3) + 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → bis(4-phenoxyphenyl)(phenyl)sulfonium trifluoromethanesulfonate

Conditions	Yield
With cesium fluoride In acetonitrile at 25℃; Inert atmosphere;	77%
With cesium fluoride In acetonitrile at 25℃; for 36h; Inert atmosphere;	35%

4,4'-Thiodiphenol (2664-63-3) + 1-bromoacetone (598-31-2) → 1,1'-((thiobis(4,1-phenylene))bis(oxy))bis(propan-2-one)

Conditions	Yield
Stage #1: 4,4'-Thiodiphenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 1-bromoacetone In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;	75%

Upstream product

• 139-65-1 4,4'-thiobisaniline 
• 7719-09-7 thionyl chloride 
• 108-95-2 phenol 
• 67-66-3 chloroform 
• 540-38-5 p-Iodophenol 
• 17755-35-0 tris-(4-hydroxy-phenyl)-sulfonium ; chloride 
• 637-89-8 4-sulfanylphenol 
• 71597-85-8 (p-hydroxyphenyl)boronic acid 
• 106-48-9 4-chloro-phenol 
• 1774-34-1 bis(4-hydroxyphenyl) sulfoxide 
• 106-41-2 4-bromo-phenol 
• 62-53-3 aniline 
• 7732-18-5 water 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 93656-74-7 2,4-Bis-(4-nitro-phenylazo)-phenol 
• 637-89-8 4-sulfanylphenol 
• 80-09-1 4,4'-sulfonediphenol 
• 40654-51-1 2,6,2',6'-tetrabromo-4,4'-sulfanediyl-di-phenol 
• 63449-96-7 thiobis(4,1-phenylene) diacetate 
• 63538-11-4 2-{4-[4-(1-Ethoxycarbonyl-heptyloxy)-phenylsulfanyl]-phenoxy}-octanoic acid ethyl ester 
• 88101-75-1 tris(4-hydroxyphenyl)sulphonium 
• 1774-34-1 bis(4-hydroxyphenyl) sulfoxide 
• 120397-54-8 phenylbis-(4-tert-butoxycarbonyloxyphenyl)sulfonium hexafluoroarsenate 
• 105112-85-4 4,4'-bis(3-nitrophenoxy)diphenyl sulfide 
• 104082-83-9 tetrakis(2,6-di-t-butyl-4-methylphenyl) 4,4'-thiobisphenyl diphosphite 
• 91829-22-0 bis [4-[(ethoxy)(propylthio)phosphoryloxy]phenyl]sulfide 
• 3383-96-8 temephos 
• 956226-13-4 [Tl2(μ-4,4'-thiodiphenol-H)2(H2O)]n 

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