3294-03-9

Basic information

• Product Name: 2,2'-Thiodi(4-tert-octylphenol)
• Synonyms: 2,2’-thiobis[4-(1,1,3,3-tetramethylbutyl)-pheno;Phenol, 2,2'-thiobis[4-(1,1,3,3-tetramethylbutyl)-;HOPS;BIS(2-HYDROXY-5-TERT-OCTYLPHENYL) SULFIDE;2,2'-thiobis[4-(1,1,3,3-tetramethylbutyl)phenol];2,2'-THIOBIS(4-TERT-OCTYLPHENOL);2,2'-Thiodi(4-tert-octylphenol);Thiobisoctylphenol
• CAS NO: 3294-03-9
• Molecular Formula: C₂₈H₄₂O₂S
• Molecular Weight: 442.7
• EINECS: 221-959-3
• Mol File: 3294-03-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 133-135°C
• Boiling Point: 524.812 °C at 760 mmHg
• Flash Point: 254.339 °C
• Appearance: /
• Density: 1.057 g/cm³
• PKA: 8.86±0.50(Predicted)
• CAS DataBase Reference: 2,2'-Thiodi(4-tert-octylphenol)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Thiodi(4-tert-octylphenol)(3294-03-9)
• EPA Substance Registry System: 2,2'-Thiodi(4-tert-octylphenol)(3294-03-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 3294-03-9(Hazardous Substances Data)

Usage

Description

2,2'-Thiodi(4-tert-octylphenol) is an organic compound that belongs to the class of thiodiphenol derivatives. It is characterized by the presence of a sulfur atom connecting two 4-tert-octylphenol molecules. This unique structure endows it with various properties that make it suitable for a range of applications across different industries.

Uses

Used in Pharmaceutical Industry:
2,2'-Thiodi(4-tert-octylphenol) is used as an active pharmaceutical ingredient for the treatment of various conditions. It is known for its analgesic, anthelmintic, sedative/hypnotic, and attention deficit-hyperactivity disorder (ADHD) therapeutic properties. 2,2'-Thiodi(4-tert-octylphenol)'s ability to alleviate pain, eliminate parasites, and induce sleep makes it a versatile agent in the pharmaceutical field.
Used in Menopause Management:
2,2'-Thiodi(4-tert-octylphenol) is used as a treatment for menopausal symptoms, helping to alleviate the discomfort and hormonal imbalances associated with this stage of life. Its effectiveness in managing menopausal symptoms contributes to improving the quality of life for women going through this transition.
Used in Sedative Prescription Weaning:
In addition to its other applications, 2,2'-Thiodi(4-tert-octylphenol) is used to help patients wean off conventional sedative prescriptions. By providing an alternative means of achieving the desired sedative effects, this compound can assist in reducing dependency on potentially addictive medications and promote a healthier approach to managing sleep and anxiety disorders.

Synthetic route

tert-octylphenol (140-66-9) → 2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol (3294-03-9)

Conditions	Yield
With sulfur dichloride In hexane at 0 - 20℃;	43.9%

tetramethoxytitanium + methanol (67-56-1) + 2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol (3294-03-9) → [Ti2(μ-methylato)2(methylato)2(κ3-2,2'-thiobis[4-(1,1,3,3-tetramethylbutyl)phenolato])2] (775312-45-3)

Conditions	Yield
In methanol byproducts: CH3OH; N2, equimol., Ti compd. added to a soln. of S compd., stirred at room temp. for 12 h; ppt. filtered, washed (methanol), dried (vac.); elem. anal.;	95%

Vanadium (III) chloride-(tris-tetrahydrofuran) (131063-11-1, 16997-51-6, 19559-06-9) + 2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol (3294-03-9) + acetonitrile (75-05-8) → [V2(μ-2,2'-thiobis(4-(1,1,3,3-tetramethylbutyl)phenolato)-κ3-O,S,O)2Cl2(CH3CN)2]*4CH3CN

Conditions	Yield
In toluene byproducts: HCl; (N2, Schlenk) to a soln. of complex in toluene was added thio-compound, the mixt. was stirred at room temp. for 48 h, volatiles were removed in vac., the solid was dissolved in CH3CN, stirred for 3 h; ppt. was filtered off, washed with cold CH3CN, dried under vac.; elem. anal.;	92%

2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol (3294-03-9) + vanadium(V) oxytriethoxide (1686-22-2) → [V2(μ-OEt)2(2,2'-thiobis(4-(1,1,3,3-tetramethylbutyl)phenolato)-κ3-O,S,O)2(O)2]

Conditions	Yield
In toluene byproducts: C2H5OH; (N2, Schlenk) to a soln. of V-compound in toluene was added thio-compound, the mixt. was stirred at room temp. for 2 h; volatiles were removed, the residue was dissolved in hot n-hexane, ppt. was filtered off, washed with n-hexane, dried in vac.; elem. anal.;	91%

titanium(IV) tetraethanolate + ethanol (64-17-5) + 2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol (3294-03-9) → [Ti2(μ-ethylato)2(ethylato)2(κ3-2,2'-thiobis[4-(1,1,3,3-tetramethylbutyl)phenolato])2] (775312-46-4)

Conditions	Yield
In ethanol byproducts: ethanol; N2, equimol., Ti compd. added to a soln. of S compd., stirred at room temp. for 12 h; ppt. filtered, washed (methanol), dried (vac.); elem. anal.;	90%

(pentamethylcyclopentadienyl)tetramethyltantalum + 2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol (3294-03-9) → [TaCp*Me2(κ3-2,2'-thiobis(6-tert-octylphenolato)] (1058140-57-0)

Conditions	Yield
In toluene byproducts: CH4; (N2); stirring a mixt. of Ta complex and ligand in toluene at 100°C for 8 h; evapn.; elem. anal.;	89%

2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol (3294-03-9) + titanium tetrachloride (7550-45-0) → (μ-2,2'-thiobis[4-(1,1,3,3-tetramethylbutyl)phenolato]-κ2O,O)(μ-2,2'-thiobis[4-(1,1,3,3-tetramethylbutyl)phenolato]-κ3O,S,O)(2,2'-thiobis[4-(1,1,3,3-tetramethylbutyl)phenolato]-κ3O,S,O)dichlorodititanium(IV)

Conditions	Yield
In hexane byproducts: HCl; under N2; S compd. (1.5 equiv.) added to soln. of TiCl4 in n-hexane, mixt. stirred at room temp. for 48 h; volatiles removed under vac., residue washed with hexane, ppt. filtered off, washed with hexane, dried under vac.; elem. anal.;	86%

2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol (3294-03-9) + trimethylaluminum (75-24-1) → [Al2(μ-κ3-O,S,O-2,2'-thiobis(4-(1,1,3,3-tetramethylbutyl)phenolato))2Me2] (862843-77-4)

Conditions	Yield
In toluene byproducts: methane; under N2; toluene soln. of AlMe3 added to cooled (273 K) soln. of ligand(1 equiv.) in toluene; warmed to room temp.; stirred for 12 h; filtered; ppt. washed with hexane; dried under vac.; elem. anal.;	84%

2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol (3294-03-9) + hafnium tetrachloride (13499-05-3) → [Hf(2,2'-thiobis(4-(1,1,3,3-tetramethylbutyl)phenolato)-κ3O,S,O)2] (918663-95-3)

Conditions	Yield
In toluene byproducts: HCl; (N2); addn. of ligand to a suspn. of metal salt in toluene, reflux for 48 h; filtration, evapn. in vac.; elem. anal.;	82%

2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol (3294-03-9) + hafnium tetrachloride (13499-05-3) → [Hf2(μ-2,2'-thiobis(4-(1,1,3,3-tetramethyl-butyl)phenolate)-κ3O,S,O)2Cl4] (1198796-50-7)

Conditions	Yield
In toluene byproducts: HCl; (N2); to suspn. of HfCl4 in toluene was added thiobisphenol, stirred at room temp. for 48 h; evapd. in vac., elem. anal.;	82%

2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol (3294-03-9) + titanium tetrachloride (7550-45-0) → bis(μ-2,2'-thiobis[4-(1,1,3,3-tetramethylbutyl)phenolato]-κ3O,S,O)tetrachlorodititanium(IV) (862981-25-7)

Conditions	Yield
In hexane byproducts: HCl; under N2; S compd. (1 equiv.) added to soln. of TiCl4 in n-hexane, mixt.refluxed for 48 h; ppt. filtered off, washed with cold Et2O, dried under vac.; elem. anal.;	80%
In diethyl ether byproducts: HCl; under N2; S compd. (1 equiv.) added to soln. of TiCl4 in Et2O, mixt. refluxed for 48 h; ppt. filtered off, washed with cold Et2O, dried under vac.; elem. anal.;	80%

pentamethylcyclopentadienyl tantalum(V) tetrachloride + 2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol (3294-03-9) → [TaCp*Cl2(κ3-2,2'-thiobis(6-tert-octylphenolato)] (1058140-53-6)

Conditions	Yield
With triethylamine In toluene byproducts: triethylammonium chloride; (N2); addn. of amine to a soln. of Ta complex and ligand in toluene, stirring at 100°C for 12 h, cooling to room temp.; filtration, extn. with toluene, evapn., washing with cold pentane, crystn. (pentane); elem. anal.;	79%

2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol (3294-03-9) + zirconium(IV) chloride (10026-11-6) → [Zr2(μ-2,2'-thiobis(4-(1,1,3,3-tetramethyl-butyl)phenolate)-κ3O,S,O)2Cl4] (1198796-49-4)

Conditions	Yield
In toluene byproducts: HCl; (N2); to suspn. of ZrCl4 in toluene was added thiobisphenol, stirred at room temp. for 48 h; evapd. in vac., elem. anal.;	73%

2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol (3294-03-9) + zirconium(IV) chloride (10026-11-6) → [Zr(2,2'-thiobis(4-(1,1,3,3-tetramethylbutyl)phenolato)-κ3O,S,O)2] (918663-94-2)

Conditions	Yield
In toluene byproducts: HCl; (N2); addn. of ligand to a suspn. of metal salt in toluene, reflux for 48 h; filtration, evapn. in vac.; elem. anal.;	55%

tetrakis(dimethylamido)titanium(IV) + 2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol (3294-03-9) → bis(2,2'-thiobis[4-(1,1,3,3-tetramethylbutyl)phenolato]-κ3O,S,O)titanium(IV) (128578-43-8, 863120-93-8)

Conditions	Yield
In hexane under N2; S compd. added to soln. of Ti complex in hexane, mixt. refluxed for 6 h; volatiles removed under vac., residue dissolved in hexane, stored at room temp. for several d, crysts. sepd.; elem. anal.;	15.8%
In not given

bis(2-isopropyl-5-methylphenyl)phosphorochloridite (220451-04-7) + 2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol (3294-03-9) → C68H92O6P2S

Conditions	Yield
With triethylamine In toluene at -10 - 25℃; for 18h;

2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol (3294-03-9) → C56H68O6P2S

Conditions	Yield
Stage #1: ortho-cresol With triethylamine; phosphorus trichloride In toluene at -15℃; for 2h; Stage #2: 2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol In toluene at -15 - 25℃; for 18h;

2,2'-thiobis-4,4'-(1,1,3,3-tetramethylbutyl)phenol (3294-03-9) + aluminum ethoxide (555-75-9) → [Al2(μ-ethoxo)2(κ3-O,S,O-2,2'-thiobis(4-(1,1,3,3-tetramethylbutyl)phenolato))2] (862843-79-6)

Conditions	Yield
In toluene under N2;

Upstream product

• 140-66-9 tert-octylphenol 

Relevant articles and documents

The synthesis of thiobisphenols from 3-alkylphenols derived from natural phenolic lipids

3-Alkylphenols derived from renewable natural resources have been used to synthesise thiobisphenols by reaction with sulfur dichloride. In contrast to previous work, we have found that 3-alkylphenols give isomeric products, the major symmetrical, the 4,4′-thiobis compound, the minor symmetrical, 2,2′-thiobisphenol, and some of the believed unsymmetrical isomer. The role of the solvent and catalyst have been studied in the reaction of 3-pentadecylphenol with sulfur dichloride. Evidence for the structures of the 2,2′ and 4,4′ isomers has been obtained from related reactions of 4-bromo-3-methylphenol, 2-bromo-5-methylphenol and their chloro analogues.