2-Hydroxyethyl disulfide

Base Information

• Chemical Name: 2-Hydroxyethyl disulfide
• CAS No.: 1892-29-1
• Molecular Formula: C4H10 O2 S2
• Molecular Weight: 154.254
• Hs Code.: 29309099
• European Community (EC) Number: 217-576-6
• NSC Number: 33920
• UNII: 45543L74BS
• DSSTox Substance ID: DTXSID4044404
• Nikkaji Number: J49.832G
• Wikidata: Q27093475
• Metabolomics Workbench ID: 52334
• ChEMBL ID: CHEMBL1233278
• Mol file: 1892-29-1.mol

Synonyms:2-hydroxyethyl disulfide;bis(2-hydroxyethyl) disulfide;bis-(2-hydroxyethyl)-disulfide;HEDS compound

Chemical Property of 2-Hydroxyethyl disulfide

Chemical Property:

• Appearance/Colour: clear to yellowish liquid
• Vapor Pressure: 7.17E-05mmHg at 25°C
• Melting Point: 25 - 27 C
• Refractive Index: n20/D 1.57(lit.)
• Boiling Point: 158 - 163 C at 3.5 mm Hg
• PKA: 14.02±0.10(Predicted)
• Flash Point: 149.3 ºC
• PSA: 91.06000
• Density: 1.312 g/cm³
• LogP: 0.35240
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Soluble in water, ethanol, acetone, and ether.
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 154.01222190
• Heavy Atom Count: 8
• Complexity: 37

Purity/Quality:

99.9% ^*data from raw suppliers

2,2''-Dithiodiethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 6.1 (Packing Group: III) UN NO.
• Hazard Codes: T
• Statements: 25-41
• Safety Statements: 26-39-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds
• Canonical SMILES: C(CSSCCO)O
• Uses: Bis(2-hydroxyethyl) disulfide is used as an intermediate in chemical research.

Technology Process of 2-Hydroxyethyl disulfide

There total 63 articles about 2-Hydroxyethyl disulfide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

disulfanediylbis(ethane-2,1-diyl) bis(2,2,2-trichloroethyl) bis(carbonate) → bis(2-hydroxyethyl) disulfide (1892-29-1)

Guidance literature:

With trimethyltin(IV) hydroxide; In 1,2-dichloro-ethane; at 60 ℃; for 14h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.8b03642

Reference yield: 88.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 3H-1,2-Benzodithiol-3-one 1,1-dioxide (66304-01-6) + 2-hydroxyethanethiol (60-24-2) → bis(2-hydroxyethyl) disulfide (1892-29-1) + methyl 2-(methylthio)benzoate (3704-28-7) + bis[2-(methoxycarbonyl)phenyl]disulfide (5459-63-2) + 2-(2'-hydroxyethyldithio)carboxymethylbenzene

Guidance literature:

3H-1,2-Benzodithiol-3-one 1,1-dioxide; 2-hydroxyethanethiol; With water; In acetonitrile; for 0.166667h;

diazomethane; In diethyl ether; at 24 ℃; for 0.0833333h; Further byproducts given;

DOI:10.1016/S0960-894X(00)00125-6

Reference yield: 81.0%

4-(3-tert-butyldimethylsilyloxyphenyl)-4-methoxyspiro<1,2-dioxetane-3,2'-adamantane> (111807-83-1) + 2-hydroxyethanethiol (60-24-2) → bis(2-hydroxyethyl) disulfide (1892-29-1) + [[(3-tert-butyldimethylsilyloxy)phenyl]-2-hydroxyadamantan-2-yl]methanone

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 3h; Time; Solvent;

DOI:10.1021/acs.joc.0c00569

upstream raw materials:

oxirane

di-α-chloroethyldisulfide

2-hydroxyethanethiol

2-chloro-ethanol

Downstream raw materials:

S-(2-hydroxyethylmercapto)-L-cysteine

1,4-Dithiane

2-hydroxyethanethiol

Oxidized glutathione

Refernces

• 1、 Sisler et al.. "-". . p. 1742. Retrieved 1970.
• 2、 Vashurin, Artur,Kuzmin, Ilya,Razumov, Mikhail,Pukhovskaya, Svetlana,Golubchikov, Oleg,Voronina, Alena,Shaposhnikov, Gennady,Koifman, Oscar. "Sulfonated Co(II) phthalocyanines covalently anchored at organic polymers as catalyst for mild oxidation of mercaptans". . p. 1159 - 1167. Retrieved 2015.
• 3、 Hajjami, Maryam,Yousofvand, Zakieh. "Preparation and characterization of organically modified MCM-48 as heterogonous catalyst for oxidation of sulfides and thiols". . p. 1733 - 1740. Retrieved 2015.
• 4、 Whitesides, George M.,Houk, Janette,Patterson, Mark A. K.. "Activation Parameters for Thiolate-Disulfide Interchange Reactions in Aqueous Solution". . p. 112 - 115. Retrieved 1983.
• 5、 Mahdian, Abolfazl,Ardakani, Mehdi Hatefi,Heydari-Bafrooei, Esmaeil,Saeednia, Samira. "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". . . Retrieved 2021.
• 6、 Fleischer, Holger,Schollmeyer, Dieter. "Functionalized tellurium(II) thiolates: Tellurium bis(2-hydroxyethanethiolate) hydrate, the first H2O - Te(II) complex". . p. 3705 - 3706. Retrieved 2000.
• 7、 Molaei, Somayeh,Ghadermazi, Mohammad,Moeini, Nazanin. "Fabrication of La (III) supported on CoFe2O4 MNPs: a novel and efficient heterogeneous catalyst for selective oxidation of sulfides and synthesis of symmetrical disulfides". . p. 771 - 793. Retrieved 2021/12/02.
• 8、 -. "Dihydric alcohol containing disulfide bond as well as preparation method and application thereof". Paragraph 0056; 0063; 0074-0109. . Retrieved 2021/03/31.