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2,2'-Dithiobis(acetamide)

Updated: 2026-08-06

Overview

2,2'-Dithiobis(acetamide) is an organic disulfide compound characterized by its acetamide-terminated structure. It serves as a versatile building block in biochemical research, particularly in studying protein disulfide bond formation and redox processes. The compound's ability to participate in thiol-disulfide exchange reactions makes it valuable for investigating enzymatic mechanisms and cellular redox regulation. Industrially, it finds use as an intermediate in specialty chemical synthesis. Its dual functionality (disulfide bridge and amide groups) allows for diverse derivatization, enabling applications in polymer chemistry and material science. The compound is typically supplied as a high-purity crystalline solid for laboratory and industrial use.

Physical and Chemical Properties

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As a crystalline solid, 2,2'-Dithiobis(acetamide) exhibits moderate stability under standard conditions but may decompose upon prolonged exposure to heat or moisture. Its disulfide bond (S-S) is redox-active, capable of undergoing reduction to thiol groups or participating in exchange reactions. The compound's water solubility distinguishes it from many hydrophobic disulfides, facilitating its use in aqueous biochemical systems. The amide groups contribute to hydrogen bonding capacity, influencing its crystalline structure and solubility profile. Thermal analysis typically shows decomposition before melting, with the exact temperature range dependent on heating rate and atmospheric conditions. Spectroscopic characteristics include distinct IR absorption bands for S-S (500 cm⁻¹) and amide (1650 cm⁻¹) functional groups.

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Main Applications

In biochemical research, 2,2'-Dithiobis(acetamide) serves as a model compound for studying disulfide bond chemistry in proteins. It's used to investigate enzymatic systems like thioredoxin and protein disulfide isomerase, which regulate cellular redox states. The compound also functions as a mild oxidizing agent for thiol group protection in peptide synthesis. Industrial applications include its use as a crosslinking agent in specialty polymer formulations, particularly where reversible redox-responsive properties are desired. Some pharmaceutical applications explore its potential as a prodrug moiety due to its reducible disulfide linkage. In material science, it contributes to the development of dynamic covalent networks and self-healing materials.

Safety and Storage

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While not classified as highly hazardous, 2,2'-Dithiobis(acetamide) requires careful handling due to potential irritant effects. Direct contact with skin or eyes may cause irritation, necessitating PPE including gloves and safety goggles. Inhalation of dust should be avoided through proper ventilation or respiratory protection when handling powders. Storage should maintain product integrity in tightly sealed containers, protected from moisture and strong oxidizers. Temperature-controlled storage (15-25°C) is recommended for long-term stability. Spills should be contained with inert absorbents and disposed of as chemical waste according to local regulations. Shelf life typically exceeds two years when stored properly.

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B2B Procurement Guide

When sourcing 2,2'-Dithiobis(acetamide), prioritize suppliers who provide comprehensive certificates of analysis (CoA) including HPLC purity verification and residual solvent data. Technical specifications should confirm molecular identity through NMR or mass spectrometry. For research applications, opt for reagent-grade material (≥98% purity); industrial users may consider technical-grade alternatives after compatibility testing. Batch sizes typically range from 100g to 25kg, with pricing tiers reflecting quantity and purity requirements. Lead times vary from stock availability to 4-6 weeks for custom synthesis. Quality verification should include checks for discoloration (indicating oxidation) and moisture content. Consider suppliers with ISO 9001 certification for consistent quality assurance.

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