1892-29-1

Basic information

• Product Name: 2,2'-DITHIODIETHANOL
• Synonyms: HYDROXYETHYL DISULFIDE;DITHIODIGLYCOL;DI-(2-HYDROXYETHYL) DISULFIDE;BIS(2-HYDROXYETHYL) DISULFIDE;BIS(2-HYDROXYETHYL) DISULPHIDE;2-HYDROXYETHYL DISULFIDE;2,2'-DITHIOBISETHANOL;2,2'-DITHIODIETHANOL
• CAS NO: 1892-29-1
• Molecular Formula: C₄H₁₀O₂S₂
• Molecular Weight: 154.25
• EINECS: 217-576-6
• Product Categories: Analytical Chemistry;Mass Spectrometry;Matrix Materials (FABMS & liquid SIMS)
• Mol File: 1892-29-1.mol

Chemical Properties

• Melting Point: 25-27 °C(lit.)
• Boiling Point: 158-163 °C3.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /liquid
• Density: 1.29 g/mL at 20 °C(lit.)
• Vapor Pressure: 7.17E-05mmHg at 25°C
• Refractive Index: n20/D 1.57(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.02±0.10(Predicted)
• Water Solubility: Soluble in water, ethanol, acetone, and ether.
• BRN: 1735851
• CAS DataBase Reference: 2,2'-DITHIODIETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-DITHIODIETHANOL(1892-29-1)
• EPA Substance Registry System: 2,2'-DITHIODIETHANOL(1892-29-1)

Safety Data

• Hazard Codes: T
• Statements: 25-41
• Safety Statements: 26-39-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: KK7525000
• F: 13
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1892-29-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research:
2,2'-DITHIODIETHANOL is used as an intermediate in chemical research for its ability to participate in various chemical reactions, such as the formation of disulfide bonds in peptides and proteins, and the synthesis of other organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,2'-DITHIODIETHANOL is used as a building block for the development of new drugs, particularly those targeting the thiol groups in proteins and enzymes. Its disulfide bond can be exploited to create molecules with specific biological activities.
Used in Material Science:
2,2'-DITHIODIETHANOL can be utilized in the development of novel materials, such as polymers and coatings, that exhibit unique properties due to the presence of disulfide bonds. These materials can find applications in various industries, including electronics, automotive, and aerospace.
Used in Environmental Applications:
2,2'-DITHIODIETHANOL can be employed in environmental applications, such as the remediation of contaminated sites and the treatment of wastewater. Its ability to form disulfide bonds can be used to immobilize or detoxify harmful substances, making it a valuable tool in environmental protection efforts.

Synthesis Reference(s)

Journal of the American Chemical Society, 80, p. 838, 1958 DOI: 10.1021/ja01537a022Synthesis, p. 50, 1978

Safety Profile

Poison by intraperitoneal route. When heated to decomposition it emits toxic fumes of SOx,.

InChI:InChI=1/C4H10O2S2/c5-1-3-7-8-4-2-6/h5-6H,1-4H2

Upstream product

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Downstream Products

• 505-29-3 1,4-Dithiane 
• 60-24-2 2-hydroxyethanethiol 
• 1077-28-7 Thioctic acid 
• 124685-36-5 2-({2-[1,1-bis(4-methoxyphenyl)-1-phenylmethoxy]ethyl}disulfanyl)ethanol 
• 140705-18-6 (S)-5-[3-(2-Hydroxy-ethylsulfanyl)-5-methoxy-4-propoxy-phenyl]-dihydro-furan-2-one 
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• 137300-55-1 (3R,6S)-[1,2]Dithiane-3,6-dicarboxylic acid bis-dimethylamide 
• 14409-87-1 pyropheophytin a 
• 24533-72-0 pyropheophorbide a 
• 5271-38-5 2-methylmercapto-ethanol 
• 1308398-43-7 2-((2-(((4-methoxyphenyl)diphenylmethyl)amino)ethyl)disulfanyl)ethan-1-ol 
• 1391914-41-2 2-((2-(prop-2-yn-1-yloxy)ethyl)disulfanyl)ethanol 
• 1355150-70-7 bis(2-ethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3-di-O-benzoyl-β-L-fucopyranoside) disulfide 
• 53606-34-1 4-(2-hydroxy-ethylsulfanyl)-benzaldehyde 

Relevant articles and documents

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The kinetics and mechanism of reduction of cobalt(II) 4,4',4'',4'''-tetrasulfophthalocyanine by 2-mercaptoethanol to yield cobalt(I) tetrasulfophthalocyanine and 2-hydroxyethyl disulfide under anoxic conditions were investigated and the following rate law was found: ν = -dIITSP>T/dt = 2K1TIITSP>T>/H+/Ka1 + Ka2/aH+)(1 + αT)>, where k2 is a rate constant for the rate-limiting electron-transfer step, and K1 is the equilibrium constant for the complexation of a CoTSP dimer with thioethanol; Ka1 and Ka2 are the apparent acid dissociation constants of HOC2H4SH and HOC2H4S-, respectively; α is K1/(1 + aH+/Ka1 + Ka2/aH+); aH+ is the hydrogen ion activity.A nonlinear least-squares fit of the experimental data to the above rate law gave k2 = 228 +/- 3.8 s-1 and K1 = 117 +/- 2.5 M-1 at 27 deg C at μ = 0.4 M.

Chalcogen-containing analogs of ethylene glycol and its derivatives

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Sulfonated Co(II) phthalocyanines covalently anchored at organic polymers as catalyst for mild oxidation of mercaptans

Current work is devoted to covalent immobilization of sulfonated derivatives of cobalt phthalocyanines "Merox catalysts" on the surfaces of polypropylene and polyethylene terephthalate. Their catalytic activity in reaction of mild oxidation of sulfur compounds to disulfides with oxygen of the air was studied. Anchoring of the catalyst on this polymer prevents its leaching and promotes its efficient recovering and recycling without significant loss of catalytic activity.

Preparation and characterization of organically modified MCM-48 as heterogonous catalyst for oxidation of sulfides and thiols

MCM-48 mesoporous synthesized and grafted with aminopropyl triethoxysilane (APTES) and subsequently reacted by isatin to obtain the imine of MCM-48. Addition of ZrOCl2.8H2O, leading to form the complex of Zr(IV)/isatin-MCM-48 as new Schiff base complex of zirconium(IV)-modified-MCM-48. The synthesized catalyst was characterized by XRD, TGA, FT-IR and BET. The resulting catalyst was efficient for selective oxidation of sulfides to sulfoxides and oxidation of thiols to disulfides with hydrogen peroxide. In this method isolation and reusability of catalyst have been investigated.

Activation Parameters for Thiolate-Disulfide Interchange Reactions in Aqueous Solution

We have measured activation parameters for thiolate-disulfide interchange reactions in water.Two disulfides were examined (Ellman's reagent and oxidized glutathione) and three thiols (2-mercaptoethanol, 1,3-dithiopropan-2-ol, and 1,4-dithiothreitol).These values are consistent with the interpretation of this reaction as an uncomplicated SN2 reaction of thiolate anion on the disulfide bond.

Thiol-dependent DNA cleavage by 3H-1,2-benzodithiol-3-one 1,1-dioxide

Hydrodisulfides (RSSH) have previously been implicated as key intermediates in thiol-triggered oxidative DNA damage by the antitumor agent leinamycin. In an effort to better understand DNA damage by RSSH and to expand on the number and type of chemical systems that produce this reactive intermediate, the ability of 3H-1,2-benzodithiol-3-one 1,1-dioxide (11) to serve as a thio-dependent DNA cleaving agent has been investigated. The findings reported here indicate that reaction of 11 with thiols results in release of RSSH and subsequent oxidative DNA strand cleavage. (C) 2000 Elsevier Science Ltd. All rights reserved.

Oxo-vanadium(IV) unsymmetrical Schiff base complex immobilized on γ-Fe2O3 nanoparticles: A novel and magnetically recoverable nanocatalyst for selective oxidation of sulfides and oxidative coupling of thiols

In this research, an unsymmetrical salen-type oxo-vanadium(IV) complex, [VO(salenac-OH)] (salenac-OH = [9-(2′,4′-dihydroxyphenyl)-5,8-diaza-4-methylnona-2,4,8-trienato](-2)), was synthesized and covalently immobilized on the surface of magnetic γ-Fe2

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The kinetics of reaction between triarylphosphanes and two newly prepared dioxorhenium(VII) compounds has been evaluated. The compounds are MeReVII(O)2( O,S ) in which O,S represents an alkoxo, thiolato chelating ligand. With MeReO3, ligands derived from 1-mercaptoethanol and 1-mercapto-2-propanol form MeRe(O)2(met), 2, and MeRe(O)2(m2p), 3. These compounds persist in chloroform solution for several hours at room temperature and for 2-3 weeks at -22°C, particularly when water is carefully excluded. They were obtained as red oils with clean 1H NMR spectra, but attempts to obtain pure, crystalline products were not successful because one decomposition pathway shows a kinetic order >1. The fastest reaction occurs between P(p-MeOC6H4)3 and 2; k298 = 215(7) L mol-1 s-1 in chloroform at 25(1)°C. The other rate constants follow a Hammett correlation against 3σ, with ρ = -0.69(7). This study relates to oxygen atom transfer reactions catalyzed by MeReO(mtp)PPh3, 1, in which MeRe(O)2(mtp), 4, is a postulated intermediate that does not build up to a measurable concentration during the catalytic cycle. Compound 2 does not react with MeSTol, but MeS(O)Tol was formed when tert-butyl hydroperoxide was added. This suggests that equilibrium lies to the left in this reaction, 2 + MeSTol + L = MeReO(met)L + MeS(O)Tol, and is drawn to the right by a reaction between MeReO(met)L and the hydroperoxide. Triphenyl arsane does not react with 2, but thermodynamic versus kinetic barriers were not resolved.

Functionalized tellurium(II) thiolates: Tellurium bis(2-hydroxyethanethiolate) hydrate, the first H2O - Te(II) complex

Photochemically labile Te(CH2CH2OH)2 is the first tellurium(II) thiolate with functionalized side chains. Its H2O complex, Te(CH2CH2OH)2·H2O (see structure), is stabil

Silica sulfuric acid/NaNO2 as a novel heterogeneous system for production of thionitrites and disulfides under mild conditions

Neat chlorosulfonic acid reacts with silica gel to give silica sulfuric acid in which sulfuric acid is immobilized on the surface of silica gel via covalent bond. Thiols can be readily converted to their corresponding thionitrites with a combination of silica sulfuric acid, wet SiO2 and sodium nitrite in dichloromethane at room temperature. Disulfides result from the homolytic cleavage of the sulfur-nitrogen bond of the unstable thionitrites and subsequent coupling of the resultant thiyl radicals.