96-69-5

Basic information

• Product Name: 4,4'-Thiobis(6-tert-butyl-m-cresol)
• Synonyms: 5-TERT-BUTYL-4-HYDROXY-2-METHYLPHENYL SULFIDE;4,4'-Thiobis(3-methyl-6-tert-butylphenol);4,4'-THIO-BIS-(6-T-BUTYL-3-METHYLPHENOL);4,4'-THIOBIS(2-T-BUTYL-5-METHYLPHENOL);4,4'-THIOBIS(2-TERT-BUTYL-5-METHYLPHENOL);4,4'-THIOBIS(6-TERT-BUTYL-M-CRESOL);4,4-THIOBIS(6-TERT-BUTYL-M-CRESOL);1,1'-Thiobis(2-methyl-4-hydroxy-5-tert-butylbenzene)
• CAS NO: 96-69-5
• Molecular Formula: C₂₂H₃₀O₂S
• Molecular Weight: 358.54
• EINECS: 202-525-2
• Product Categories: Industrial/Fine Chemicals;Organics;TITANIUM
• Mol File: 96-69-5.mol
• Article Data: 45

Chemical Properties

• Melting Point: 160-165 °C
• Boiling Point: 460.94°C (rough estimate)
• Flash Point: 215 °C
• Appearance: White or light gray to tan powder
• Density: 1.06~1.12g/cm3
• Vapor Pressure: 1.14E-09mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 10.76±0.36(Predicted)
• Water Solubility: <0.01 g/100 mL at 18℃
• CAS DataBase Reference: 4,4'-Thiobis(6-tert-butyl-m-cresol)(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Thiobis(6-tert-butyl-m-cresol)(96-69-5)
• EPA Substance Registry System: 4,4'-Thiobis(6-tert-butyl-m-cresol)(96-69-5)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-50/53-43
• Safety Statements: 37/39-26-61-60-36/37-24/25
• WGK Germany: WGK 2 water endangering
• RTECS: GP3150000
• Hazardous Substances Data: 96-69-5(Hazardous Substances Data)

Usage

Chemical Properties

4,40-Thiobis(6-tert-butyl-m-cresol) is a light gray to tan powder. Aromatic odor.

Uses

Different sources of media describe the Uses of 96-69-5 differently. You can refer to the following data:
1. As an antioxidant in the rubber and plastics industry; as a stabilizer in polyethylene and polyolefin packaging materials for foodstuffs.
2. 4,4''-Thiobis(2-tert-butyl-5-methylphenol) is an antioxidant. 4,4''-Thiobis(2-tert-butyl-5-methylphenol) is a radical inhibitor which prevented thermal decomposition of the peracid.
3. Protection of light-colored rubber from oxidation and of nonstaining neoprene compounds against deterioration.

General Description

White or light gray to tan powder.

Air & Water Reactions

Sensitive to base hydrolysis and may spontaneously oxidize in solution. . Insoluble in water.

Reactivity Profile

4,4'-Thiobis(6-tert-butyl-m-cresol) may be sensitive to light.

Health Hazard

4,4'-Thiobis(6-tert-butyl-mcresol) (TBBC) is of low systemic toxicity in animals; allergic contact dermatitis has been reported in humans.

Fire Hazard

4,4'-Thiobis(6-tert-butyl-m-cresol) is combustible.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by intraperitoneal route and probably by ingestion and inhalation. Mutation data reported. See also SULFIDES. When heated to decomposition it emits highly toxic fumes of SOx.

Potential Exposure

This material is used as an antioxidant in the plastics and rubber industries; in Neoprene and other synthetic rubbers; in polyethylene and polypropylene.

Carcinogenicity

TBBC was not mutagenic in Salmonella typhimurium strains with or without metabolic activation. In Chinese hamster ovary cells, TBBC induced an increase in sister chromatid exchanges but there were no increases in chromosomal aberrations.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. May evolve explosive hydrogen sulfide upon contact with moisture or acids.

InChI:InChI=1/C22H30O2S/c1-13-9-17(23)15(21(3,4)5)11-19(13)25-20-12-16(22(6,7)8)18(24)10-14(20)2/h9-12,23-24H,1-8H3

Synthetic route

2-tert-Butyl-5-methylphenol (88-60-8) → Santonox R (96-69-5)

Conditions	Yield
With hexane; sulfur dichloride

Santonox R (96-69-5) → 2,2'-Di-tert-butyl-5,5'-dimethyl-4,4'-sulfinyl-di-phenol (31710-39-1)

Conditions	Yield
With C28H12Br4N12OV(4+)*4CBr3(1-); dihydrogen peroxide In water; acetonitrile at 20℃; for 3h; chemoselective reaction;	63%

Santonox R (96-69-5) + 1-Bromopentane (110-53-2) → bis(5-(tert-butyl)-2-methyl-4-(pentyloxy)phenyl)sulfane

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃;	60.5%

Santonox R (96-69-5) + bis-allylnickel chloride + sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate (79060-88-1) → [Ni(4,4'-thio-bis(6-tert-butyl-m-cresol))2(η3-allyl)](B(3,5-(CF3)2C6H3)4) (1220750-96-8)

Conditions	Yield
In diethyl ether under inert atm.; using Schlenk technique; Et2O soln. of 4,4'-thio-bis(6-tert-butyl)-m-cresol and NaB((CF3)2C6H3)4 added to stirred soln. of Ni complex in Et2O at -60°C; after 2 h cooling bath removed, stirredat room temp. overnight; solvent evapd. under vac., residue extd. with CH2Cl2; soln. filtered, concd.; crystd. twice from CH2Cl2-hexane; elem. anal.;	60%

Santonox R (96-69-5) + <(2)H11>Pentyl bromide (126840-21-9) → bis(5-(tert-butyl)-2-methyl-4-(pentyl-d22-oxy)phenyl)sulfane

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85℃;	59.1%

Santonox R (96-69-5) + sodium thiomethoxide (NaSMe) + 3-chloro-4-fluoronitrobenzene (350-30-1) → 2-chloro-1-(methylsulfanyl)-4-nitrobenzene (77146-55-5)

Conditions	Yield
In N,N-dimethyl-formamide; pentane	49%
In N,N-dimethyl-formamide; pentane	49%

Santonox R (96-69-5) + 2-Fluoro-5-nitrobenzotrifluoride (400-74-8) + sodium thiomethoxide (5188-07-8) → 1-(methylsulfanyl)-4-nitro-2-(trifluoromethyl)benzene (60789-49-3)

Conditions	Yield
In N,N-dimethyl-formamide	15%
In N,N-dimethyl-formamide	15%

pyrrolidine (123-75-1) + Santonox R (96-69-5) + formaldehyd (50-00-0) → bis-(5-tert-butyl-4-hydroxy-2-methyl-3-pyrrolidinomethyl-phenyl)-sulfide (124514-35-8)

Conditions	Yield
With ethanol

piperidine (110-89-4) + Santonox R (96-69-5) + formaldehyd (50-00-0) → bis-(5-tert-butyl-4-hydroxy-2-methyl-3-piperidinomethyl-phenyl)-sulfide (124120-10-1)

Conditions	Yield
With ethanol

Santonox R (96-69-5) + Cumene hydroperoxide (80-15-9) → 2,2'-Di-tert-butyl-5,5'-dimethyl-4,4'-sulfinyl-di-phenol (31710-39-1)

Conditions	Yield
With benzene

Santonox R (96-69-5) + formaldehyd (50-00-0) + dimethyl amine (124-40-3) → 6,6'-di-tert-butyl-2,2'-bis-dimethylaminomethyl-3,3'-dimethyl-4,4'-sulfanediyl-di-phenol (117884-55-6)

Santonox R (96-69-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → Formic acid 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methyl-phenylsulfanyl)-5-methyl-phenyl ester (64833-90-5)

Conditions	Yield
With trichlorophosphate

Santonox R (96-69-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → C24H30O4S (21982-25-2)

Conditions	Yield
With trichlorophosphate

Santonox R (96-69-5) + 3-(4-methoxybenzyl)-10(9H)-oxo-3H-1,2,3-triazolo[5,4-b][1,5]benzo-thiazepine (170991-05-6) → 3-(4-methoxybenzyl)-10(9H)-oxo-3H-1,2,3-triazolo[5,4-b][1,5]benzothiazepine 4,4-dioxide (170991-07-8)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane

Santonox R (96-69-5) + β-hydroxy-α-methylene-benzeneheptanoic acid methyl ester (119513-85-8) → 2-[1-hydroxy-5-phenylpentyl]-2-oxiranecarboxylic acid methyl ester (119513-89-2)

Conditions	Yield
With m-chloroperoxybenzoic acid In ethyl acetate; 1,2-dichloro-ethane
With m-chloroperoxybenzoic acid In ethyl acetate; 1,2-dichloro-ethane
With m-chloroperoxybenzoic acid In ethyl acetate; 1,2-dichloro-ethane

Santonox R (96-69-5) + β-fluoro-α-methylbenzene-heptanoic acid methyl ester → 2-(1-Fluoro-5-phenylpentyl)-2-oxiranecarboxylic acid methyl ester

Conditions	Yield
With m-chloroperoxybenzoic acid In diethyl ether; hexane; 1,2-dichloro-ethane

Santonox R (96-69-5) + β-hydroxy-α-methylene-8-(4-chlorophenoxy)octanoic acid methyl ester (129379-64-2) → 2-[6-(4-chlorophenoxy)-1-hydroxyhexyl]-2-oxiranecarboxylic acid methyl ester

Conditions	Yield
With m-chloroperoxybenzoic acid In 1,2-dichloro-ethane
With m-chloroperoxybenzoic acid In 1,2-dichloro-ethane
With m-chloroperoxybenzoic acid In 1,2-dichloro-ethane

Santonox R (96-69-5) + β-fluoro-α-methylenebenzeneheptanoic acid methyl ester → 2-(1-Fluoro-5-phenylpentyl)-2-oxiranecarboxylic acid methyl ester

Conditions	Yield
With m-chloroperoxybenzoic acid In 1,2-dichloro-ethane
With m-chloroperoxybenzoic acid In 1,2-dichloro-ethane

Santonox R (96-69-5) + 4-allyl-6,7-dichloro-5-hydroxy-2-methyl-2-phenyl-1-indanone (61000-47-3) → 4,5-dichloro-2-(hydroxymethyl)-7-methyl-6-oxo-7-phenyl-1,2,7,8-tetrahydro-6H-indeno<5,4-b>furan (61024-51-9)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane

Santonox R (96-69-5) → C22H28Cl4O2P2S

Conditions	Yield
With phosphorus trichloride In n-heptane; toluene at 35 - 95℃; for 1.75h;

Upstream product

• 88-60-8 2-tert-Butyl-5-methylphenol 

Downstream Products

• 124514-35-8 bis-(5-tert-butyl-4-hydroxy-2-methyl-3-pyrrolidinomethyl-phenyl)-sulfide 
• 31710-39-1 2,2'-Di-tert-butyl-5,5'-dimethyl-4,4'-sulfinyl-di-phenol 
• 60789-49-3 1-(methylsulfanyl)-4-nitro-2-(trifluoromethyl)benzene 
• 77146-55-5 2-chloro-1-(methylsulfanyl)-4-nitrobenzene 
• 61024-51-9 4,5-dichloro-2-(hydroxymethyl)-7-methyl-6-oxo-7-phenyl-1,2,7,8-tetrahydro-6H-indeno<5,4-b>furan 
• 1220750-96-8 [Ni(4,4'-thio-bis(6-tert-butyl-m-cresol))2(η3-allyl)](B(3,5-(CF3)2C6H3)4) 
• 119513-89-2 2-[1-hydroxy-5-phenylpentyl]-2-oxiranecarboxylic acid methyl ester 
• 170991-07-8 3-(4-methoxybenzyl)-10(9H)-oxo-3H-1,2,3-triazolo[5,4-b][1,5]benzothiazepine 4,4-dioxide 
• 21982-25-2 C₂₄H₃₀O₄S 
• 64833-90-5 Formic acid 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methyl-phenylsulfanyl)-5-methyl-phenyl ester 
• 117884-55-6 6,6'-di-tert-butyl-2,2'-bis-dimethylaminomethyl-3,3'-dimethyl-4,4'-sulfanediyl-di-phenol 
• 124120-10-1 bis-(5-tert-butyl-4-hydroxy-2-methyl-3-piperidinomethyl-phenyl)-sulfide 

Relevant articles and documents

Synthesis method of 4,4'-thiobis(6-tert-butyl-3-methylphenol)

The invention relates to a synthesis method of 4,4'-thiobis(6-tert-butyl-3-methylphenol). According to the method, chlorine and sulfur dichloride which are necessary to use in a traditional process are avoided, and a large amount of hydrogen chloride tail gas is not generated; a byproduct silver iodide and acid liquor are easy to recover and reuse, the environmental protection property and safety of the reaction are greatly improved, and the problems of equipment corrosion and the like are avoided. Therefore, the method is suitable for industrially synthesizing the 4,4'-thiobis(6-tert-butyl-3-methylphenol).

Thioether substituted hydroxybenzophenones and stabilized compositions

2-Hydroxybenzophenone derivatives substituted in the 4′-position by a thioether moiety exhibit enhanced absorption in the UV at longer wavelength. Compositions comprising organic material subject to actinic degradation are beneficially stabilized with such derivatives.

3,9-carbohydrate substituted 2,4,8,10-tetraoxa-3,9-diphosphaspiro(5.5)undecane phosphite stabilizers

Carbohydrate substituted phosphites of Formula I STR1 where A is a carbohydrate residue are effective stabilizers for polymers processed at elevated temperatures and subject to thermal or oxidative degradation.