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4,4'-Thiobis-phenol
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Name

4,4'-Thiobis-phenol

 EINECS 220-197-9
CAS No. 2664-63-3 Density 1.37 g/cm3
PSA 65.76000 LogP 3.24900
Solubility Insoluble in water Melting Point 154-156 °C(lit.)
Formula C12H10O2S Boiling Point 452.7 °C at 760 mmHg
Molecular Weight 218.276 Flash Point 219.7 °C
Transport Information UN 3261 8/PG 2 Appearance White Crystals
Safety 26-27-36/37/39-45 Risk Codes 34
Molecular Structure Molecular Structure of 2664-63-3 (4,4'-Thiobis-phenol) Hazard Symbols CorrosiveC
Synonyms

Phenol,4,4'-thiodi- (6CI,7CI,8CI);Phenol, p,p'-thiobis- (3CI);Phenol, p,p'-thiodi-(4CI);4,4'-Dihydroxydiphenyl sulfide;4,4'-Thiobisphenol;4-(4-Hydroxyphenylthio)phenol;Bis(4-hydroxyphenyl) sulfide;Bis(p-hydroxyphenyl) sulfide;Bis(p-hydroxyphenyl)thioether;Bisphenol T;Bisphenol sulfide;NSC 203030;Thiobisphenol;p,p'-Dihydroxydiphenyl sulfide;Phenol,4,4'-thiobis-;Bis(4-oxyphenyl)sulfide;

Article Data 60

4,4'-Thiobis-phenol Synthetic route

1774-34-1

bis(4-hydroxyphenyl) sulfoxide

2664-63-3

4,4'-Thiodiphenol

Conditions
ConditionsYield
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%
108-95-2

phenol

2664-63-3

4,4'-Thiodiphenol

Conditions
ConditionsYield
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
540-38-5

4-Iodophenol

2664-63-3

4,4'-Thiodiphenol

Conditions
ConditionsYield
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%
106-41-2

4-bromo-phenol

2664-63-3

4,4'-Thiodiphenol

Conditions
ConditionsYield
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%
637-89-8

4-sulfanylphenol

71597-85-8

(p-hydroxyphenyl)boronic acid

2664-63-3

4,4'-Thiodiphenol

Conditions
ConditionsYield
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%
106-48-9

4-chloro-phenol

2664-63-3

4,4'-Thiodiphenol

Conditions
ConditionsYield
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%
108-95-2

phenol

A

2664-63-3

4,4'-Thiodiphenol

B

17755-37-2

(2-hydroxyphenyl 4-hydroxyphenyl)sulfure

Conditions
ConditionsYield
With tetraethylammonium perchlorate; trichloroacetic acid In dichloromethane for 2h; Ambient temperature; working pot.: 2.2 V vs SCE;A 48%
B 37%
106-41-2

4-bromo-phenol

A

1121-24-0

ortho-mercaptophenol

B

615-58-7

2,4-dibromophenol

C

95-56-7

2-hydroxybromobenzene

D

2664-63-3

4,4'-Thiodiphenol

E

108-95-2

phenol

Conditions
ConditionsYield
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%
...Expand
19089-85-1

p-diazophenol

A

15015-57-3

bis(4-hydroxyphenyl)disulfide

B

2664-63-3

4,4'-Thiodiphenol

Conditions
ConditionsYield
With sodium hydroxide; sodium disulfide at 90℃;
139-65-1

4,4'-thiobisaniline

2664-63-3

4,4'-Thiodiphenol

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

4,4'-Thiobis-phenol Chemical Properties


IUPAC Name: 4-(4-Hydroxyphenyl)sulfanylphenol
Canonical SMILES: C1=CC(=CC=C1O)SC2=CC=C(C=C2)O
InChI: InChI=1S/C12H10O2S/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8,13-14H
InChIKey: VWGKEVWFBOUAND-UHFFFAOYSA-N
Molecular Weight: 218.2716 [g/mol]
Molecular Formula: C12H10O2S
XLogP3: 3.3
H-Bond Donor: 2
H-Bond Acceptor: 2 
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 
Sensitive: Air Sensitive 
Index of Refraction: 1.717
Molar Refractivity: 62.53 cm3
Molar Volume: 158.7 cm3
Surface Tension: 70.6 dyne/cm
Density: 1.37 g/cm3
Flash Point: 219.7 °C
Enthalpy of Vaporization: 73.94 kJ/mol
Boiling Point: 452.7 °C at 760 mmHg
Vapour Pressure: 8.17E-09 mmHg at 25 °C
Melting Point: 154-156 °C(lit.)
Classification Code of Bis(4-oxyphenyl)sulfide (CAS NO.2664-63-3): Skin / Eye Irritant 

4,4'-Thiobis-phenol Toxicity Data With Reference

1.    

skn-rbt 500 mg MLD

     BIOFX*    BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets .(Northbrook, IL.: )1971,A408.
2.    

eye-rbt 100 mg SEV

     BIOFX*    BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets .(Northbrook, IL.: )1971,A408.
3.    

orl-rat LD50:3362 mg/kg

     BIOFX*    BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets .(Northbrook, IL.: )1971,A408.
4.    

orl-mus LD50:5500 mg/kg

     TPKVAL    Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Sciences. 13 (1973),154.

4,4'-Thiobis-phenol Consensus Reports

Reported in EPA TSCA Inventory.

4,4'-Thiobis-phenol Safety Profile

Moderately toxic by ingestion. Corrosive. A skin and severe eye irritant. When heated to decomposition Bis(4-oxyphenyl)sulfide emits toxic fumes of SOx.
Hazard Codes: CorrosiveC
Risk Statements: 34 
R34:Causes burns.
Safety Statements: 26-27-36/37/39-45 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S27:Take off immediately all contaminated clothing. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 3261 8/PG 2
WGK Germany: 2
RTECS: SN0800000
HazardClass: 8
PackingGroup: II

4,4'-Thiobis-phenol Specification

 Bis(4-oxyphenyl)sulfide (CAS NO.2664-63-3), its Synonyms are 4,4'-Dihydroxydiphenyl sulfide ; 4,4'-Dihydroxydiphenylsulfide ; 4,4'-Dioxydiphenyl sulfide ; 4,4'-Dioxydiphenylsulfide ; 4,4'-Thiobisphenol ; Bis(4-hydroxyphenyl) sulfide ; Bis(p-hydroxhphenyl) sulfide ; DFS ; Sulfide, bis(4-hydroxyphenyl) ; Thiobisphenol ; p,p'-Dihydroxydiphenyl sulfide .

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