Product Manager: Selina Zhang; Email: selina@coreychem.com
| Product Name | BIS(2,2-DIETHOXYETHYL) DISULFIDE |
| Synonyms | 1,2-Bis(2,2-diethoxyethyl) disulfide;Bis(2,2-diethoxyethyl)disulphide;Bis(2,2-diethoxyethyl)Disulfide>Disulfide, bis(2,2-diethoxyethyl);1,2-Bis(2,2-diethoxyethyl)disulfane |
| CAS NO | 76505-71-0 |
| Purity |
99% |
| Appearance |
/ |
| MF | C12H26O4S2 |
| MW | 298.47 |
| Contact | selina@coreychem.com |
BIS(2,2-DIETHOXYETHYL) DISULFIDE (CAS: 76505-71-0), also known as 1,2-Bis(2,2-diethoxyethyl) disulfide, is a symmetrical dialkyl disulfide characterized by two terminal acetal (2,2-diethoxyethyl) groups linked via a central disulfide bond. With a molecular formula of C₁₂H₂₆O₄S₂ and a molecular weight of 298.46, this compound is a lipophilic, hydrogen-bond-accepting liquid at room temperature, typically appearing as a colorless to yellow-orange clear liquid. As a bifunctional molecule featuring a central disulfide linkage and two protected aldehyde moieties, it serves as a versatile intermediate for synthetic organic chemistry, polymer modification, and stimuli-responsive material design. The compound is intended strictly for laboratory research, drug discovery, and chemical biology applications. Its primary applications are outlined below:
1. Synthetic Organic Chemistry & Heterocyclic Synthesis
Bis(2,2-diethoxyethyl) disulfide is a valuable reagent in organic synthesis, particularly for the formation of disulfide bonds in complex molecules and for facilitating C-S and C-X bond formations. It serves as a protected aldehyde source and a versatile intermediate in the construction of complex sulfur-containing molecules and heterocycles.
The compound’s mechanism of action involves the cleavage and formation of disulfide bonds. It undergoes various chemical transformations: the disulfide bond can be oxidized to form sulfoxides or sulfones using agents like hydrogen peroxide, or reduced to form thiols using reagents such as lithium aluminum hydride or sodium borohydride. Notably, it has been shown to generate formyl radicals from benzene under solar irradiation, a process that is more efficient than other known photochemical methods. The formyl group can also act as an intramolecular electrophile, reacting with electron-deficient aromatic rings to form new ring systems.
2. Pharmaceutical Development & Drug Discovery
This compound serves as a valuable intermediate in synthesizing various pharmaceuticals, particularly in the development of drugs targeting oxidative stress-related conditions. It is used as a pharmaceutical intermediate for synthesizing complex sulfur-containing active pharmaceutical ingredients. Research is ongoing to explore its potential therapeutic applications, including its use as a precursor for drug development. In biological systems, it can interact with thiol groups in proteins, leading to the formation of new disulfide bonds and potentially altering protein function through redox-mediated mechanisms.
3. Polymer Chemistry & Materials Science
In polymer chemistry, Bis(2,2-diethoxyethyl) disulfide is used in the formulation of specialty polymers, enhancing properties such as flexibility and chemical resistance, making it ideal for coatings and adhesives. It acts as a cross-linker or a monomer to enhance the properties of polymers and resins. In material science, it is utilized in creating advanced materials with unique properties, such as improved thermal stability and resistance to degradation, which are crucial in electronics and automotive industries. Its acetal-protected aldehyde and redox-responsive disulfide functionalities enable the design of stimuli-responsive polymers and thiol-disulfide exchange surface engineering.
4. Analytical & Environmental Chemistry
The compound is employed as a reagent in analytical methods to detect and quantify sulfide compounds, providing researchers with a reliable tool for environmental monitoring.
5. Agricultural Research
It acts as a potential pesticide or fungicide, offering a safer alternative to traditional chemicals, which appeals to environmentally conscious growers.
6. Handling & Storage
Storage Conditions: Store at room temperature under inert gas in tightly sealed containers. Protect from moisture, excessive heat, and direct sunlight. The acetal functional groups are sensitive to acid, making it critical to prevent deprotection and unwanted side reactions.
Purity & Appearance: Commercial grades are available with purity ≥85% (GC) for technical grade and ≥90.0% (GC) for standard grade. Appearance is a colorless to pale yellow liquid.
Physicochemical Properties: Boiling point: 155 °C at 8 mmHg; Density: ~1.036 – 1.05 g/mL; Refractive index: ~1.478.
Intended Use: This product is intended strictly for laboratory research, drug discovery, and chemical biology applications. It is not intended for therapeutic, diagnostic, food, or household applications without appropriate regulatory approval.
Summary
The value of BIS(2,2-DIETHOXYETHYL) DISULFIDE (CAS: 76505-71-0) lies in its unique dual functionality as both a protected aldehyde source (via acetal groups) and a redox-responsive disulfide bond. This combination enables controlled thiol/aldehyde release and makes it a versatile building block for synthetic organic chemistry, polymer modification, stimuli-responsive material design, and pharmaceutical development. Its applications span heterocyclic synthesis, drug discovery, specialty polymer formulation, advanced materials, analytical chemistry, and agricultural research, making it an indispensable reagent for a wide range of scientific investigations.
For more information, please contact: selina@coreychem.com
