15015-57-3

Basic information

• Product Name: BIS(4-HYDROXYPHENYL)DISULFIDE
• Synonyms: BIS(4-HYDROXYPHENYL)DISULFIDE;4,4'-DIHYDROXY DIPHENYL DISULFIDE;4,4'-DIHYDROXYDIPHENYLDISULPHIDE;4,4'-Disulfanediyldiphenol;4,4'-Dithiodiphenol;4,4'-Dihydroxy diphe;4,4'-Dihydroxydiphenyl Disulfide 4,4'-Dithiodiphenol;4,4'-Dihydroxydiphenyl Disulfide 4
• CAS NO: 15015-57-3
• Molecular Formula: C₁₂H₁₀O₂S₂
• Molecular Weight: 250.34
• Product Categories: Miscellaneous;pharmacetical
• Mol File: 15015-57-3.mol

Chemical Properties

• Melting Point: 150.0 to 154.0 °C
• Boiling Point: 437.9 °C at 760 mmHg
• Flash Point: 212.5 °C
• Appearance: /
• Density: 1.449 g/cm³
• Vapor Pressure: 2.8E-08mmHg at 25°C
• Refractive Index: 1.752
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 9.01±0.26(Predicted)
• CAS DataBase Reference: BIS(4-HYDROXYPHENYL)DISULFIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(4-HYDROXYPHENYL)DISULFIDE(15015-57-3)
• EPA Substance Registry System: BIS(4-HYDROXYPHENYL)DISULFIDE(15015-57-3)

Safety Data

• Hazardous Substances Data: 15015-57-3(Hazardous Substances Data)

Usage

Uses

Used in Rubber and Plastic Industry:
BIS(4-HYDROXYPHENYL)DISULFIDE is used as a cross-linking agent for enhancing the strength and durability of rubber and plastic materials. Its ability to form covalent bonds between polymer chains contributes to the improved mechanical properties of these materials.
Used in Cosmetics and Personal Care Products:
In the cosmetics and personal care industry, BIS(4-HYDROXYPHENYL)DISULFIDE is used as a component in various formulations due to its chemical properties. However, its presence in these products is under scrutiny due to potential health concerns.
Health Risks and Regulatory Actions:
BIS(4-HYDROXYPHENYL)DISULFIDE is recognized for potential health risks, leading to its classification as an endocrine disruptor with possible toxic effects on the reproductive system. As a result, there is a push towards limiting or eliminating its use in consumer products to protect public health. This has prompted regulatory actions and industry responses to find safer alternatives for its applications.

InChI:InChI=1/C12H10O2S2/c13-9-1-5-11(6-2-9)15-16-12-7-3-10(14)4-8-12/h1-8,13-14H

Upstream product

• 19089-85-1 p-diazophenol 
• 3774-52-5 4-thiocyanato-phenol 
• 637-89-8 4-sulfanylphenol 
• 108-95-2 phenol 
• 5335-87-5 4,4'-dimethoxyphenyl disulfide 
• 149124-52-7 Potassium; 4-hydroxy-benzenethiolate 
• 76372-46-8 1-acetoxy-4-acetylsulfanyl-benzene 
• 616-38-6 carbonic acid dimethyl ester 
• 106-48-9 4-chloro-phenol 
• 3885-04-9 4-acetoxybenzenesulfonic acid sodium salt 
• 70-18-8 GLUTATHIONE 
• 1176996-13-6 (E)-4-[(4-hydroxyphenyl)sulfanyl]but-3-en-2-one 
• 1176996-15-8 (Z)-4-[(4-hydroxyphenyl)sulfanyl]but-3-en-2-one 
• 540-38-5 p-Iodophenol 

Downstream Products

• 109697-21-4 trithioarsenous acid tris-(4-hydroxy-phenyl ester) 
• 326921-47-5 bis-(4-acetoxy-phenyl)-disulfide 
• 5335-87-5 4,4'-dimethoxyphenyl disulfide 
• 60852-03-1 bis(p-tert-butoxyphenyl) disulfide 
• 80172-75-4 4-tosyloxyphenyl disulfide 
• 141982-43-6 C₁₂H₁₀O₂S₂*C₆H₄O₂ 
• 6548-20-5 4,4'-Bis-diphenyl-disulfid 
• 167012-47-7 methyl [4-(4-[methoxycarbonylmethoxy]phenyldithio)phenoxy]acetate 
• 5633-55-6 4-phenylsulfanylphenol 
• 461-84-7 (4-trifluoromethylthio)phenol 
• 317318-65-3 methyl 2-{4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)sulfanyl]phenoxy}acetate 
• 873066-38-7 {4-[4-furan-2-yl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethylsulfanyl]-phenoxy}-acetic acid methyl ester 
• 873066-39-8 {4-[4-phenyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethylsulfanyl]-phenoxy}-acetic acid methyl ester 
• 1706-60-1 (4-Mercapto-phenoxy)-acetic Acid Methyl Ester 

Relevant articles and documents

Syntheses of alkylated malonates on a traceless linker derived soluble polymer support

A new traceless soluble polymeric linker and a corresponding alkylating strategy has been developed. Dimethyl malonate was alkylated with a variety of polymeric halides and these resulting polymer bound malonates underwent further alkylation with addition

CpMn(CO)3-catalyzed photoconversion of thiols into disulfides and dihydrogen

The UV photolysis of CpMn(CO)3 with thiols at room temperature effected the following catalytic transformation: 2 RSH → R 2S2 + H2. This reaction is a cleaner and greener way toward making disulfides, as it produces dihydrogen as the only side-product. The manganese system exhibits high chemoselectivity as the transformation proceeds efficiently even in the presence of numerous functional groups. A manganese dicarbonyl complex, CpMn(CO)2RSH, and cyclopentadiene have also been detected using FTIR and NMR spectroscopic techniques, respectively. Based on our experimental data, a mechanism has been proposed to account for the catalysis.

Flower-Like Colloidal Particles through Precipitation Polymerization of Redox-Responsive Liquid Crystals

We report on the synthesis of monodisperse, flower-like, liquid crystalline (LC) polymer particles by precipitation polymerization of a LC mixture consisting of benzoic acid-functionalized acrylates and disulfide-functionalized diacrylates. Introduction o

Green Aerobic Oxidation of Thiols to Disulfides by Flavin-Iodine Coupled Organocatalysis

Coupled catalysis using a riboflavin-derived organocatalyst and molecular iodine successfully promoted the aerobic oxidation of thiols to disulfides under metal-free mild conditions. The activation of molecular oxygen occurred smoothly at room temperature through the transfer of electrons from the iodine catalyst to the biomimetic flavin catalyst, forming the basis for a green oxidative synthesis of disulfides from thiols.

Synthesis and biological evaluation of disulfides as anticancer agents with thioredoxin inhibition

Altered redox homeostasis as a hallmark of cancer cells is exploited by cancer cells for growth and survival. The thioredoxin (Trx), an important regulator in maintaining the intracellular redox homeostasis, is cumulatively recognized as a promising target for the development of anticancer drugs. Herein, we synthesized 72 disulfides and evaluated their inhibition for Trx and antitumor activity. First, we established an efficient and fast method to screen Trx inhibitors by using the probe NBL-SS that was developed by our group to detect Trx function in living cells. After an initial screening of the Trx inhibitory activity of these compounds, 8 compounds showed significant inhibition activity against Trx. We then evaluated the cytotoxicity of these 8 disulfides, compounds 68 and 69 displayed high cytotoxicity to HeLa cells, but less sensitive to normal cell lines. Next, we performed kinetic studies of both two disulfides, 68 had faster inhibition of Trx than 69. Further studies revealed that 68 led to the accumulation of reactive oxygen species and eventually induced apoptosis of Hela cells via inhibiting Trx. The establishment of a method for screening Trx inhibitors and the discovery of 68 with remarkable Trx inhibition provide support for the development of anticancer candidates with Trx inhibition.

Preparation method of symmetric disulfide bond-containing compound

The method comprises the following steps: adding a raw material and an oxidant to a reaction bottle containing a solvent; reacting 23W - 85W under the irradiation of 12 - 24h energy-saving lamps; and purifying the reaction product to obtain symmetrical disulfide bond-containing compounds. The raw material is mercaptan or thiophenol. The oxidizing agent is trichlorobromomethane, and the solvent is tetrahydrofuran. The method has the advantages of simple operation, high yield (70 - 90%), wide applicability, cheap and easily available raw materials, and provides a better way for the synthesis and production of symmetrical disulfide bond-containing compounds.

Substituted o-Aminophenols as Redox-Mediators in the Thiol Oxidation to Unsymmetrical Disulfides

A number of substituted o-aminophenols has been investigated as redox mediators of the thiol oxidation to disulfides. The electrooxidation of o-aminophenols leads to the corresponding o-iminobenzoquinones. These compounds react with thiols in the solution with a formation of disulfides. It was established that the use of 4,6-di-tert-butyl-2-(tert-butylamino)phenol as a redox mediator can reduce the overpotential of the thiol oxidation by 0.2-1.4 V depending on the nature of the coupling thiols. The unsymmetrical disulfides with alkyl, aryl, and heteroaryl substituents were obtained as the result of the indirect electrosynthesis.

Synthetic method of diaryl disulfide compound

The invention relates to a synthetic method of a diaryl disulfide compound. The method comprises the following steps of: in an organic solvent, under the condition of nitrogen, using arylboronic acidand sulfur as the reaction raw materials, carrying out free radical vulcanization/self-polymerization coupling reaction under the action of a transition metal silver catalyst to obtain the diaryl disulfide compound. The method is simple in reaction condition, simple and convenient in experimental operation and high in product yield and purity, opens up a synthetic route and method for preparationof the diaryl disulfide compound, and has good application potential and research value.

MATRIX METALLOPROTEINASE (MMP) INHIBITORS AND METHODS OF USE THEREOF

Hydantoin based compounds useful as inhibitors of matrix metalloproteinases (MMPs), particularly macrophage elastase (MMP-12) are described. Also described are related compositions and methods of using the compounds to inhibit MMP-12 and treat diseases mediated by MMP-12, such as asthma, chronic obstructive pulmonary disease (COPD), emphysema, acute lung injury, idiopathic pulmonary fibrosis (IPF), sarcoidosis, systemic sclerosis, liver fibrosis, nonalcoholic steatohepatitis (NASH), arthritis, cancer, heart disease, inflammatory bowel disease (IBD), acute kidney injury (AKI), chronic kidney disease (CKD), Alport syndrome, and nephritis.

Natural gallic acid catalyzed aerobic oxidative coupling with the assistance of MnCO3 for synthesis of disulfanes in water

The formation of S-S bonds has great significance and value in synthetic chemistry and bioscience. To pursue a sustainable approach for such a synthesis, an aerobic oxidative coupling method for the efficient preparation of organic disulfanes, using a low-toxic natural gallic acid as an organocatalyst, inexpensive MnCO3 as a cocatalyst, O2 as the terminal oxidant and water as the solvent, has been successfully developed. Such metal-organic cooperative catalytic protocol provided an access to various symmetrical and unsymmetrical disulfanes in up to 99% yield. Gram scale synthesis with practical convenience and low loading of catalysts further illustrates the practicability of our method.