Dimethyl sulphoxide

Base Information

• Chemical Name: Dimethyl sulphoxide
• CAS No.: 67-68-5
• Deprecated CAS: 164071-41-4,8070-53-9,705301-21-9,1173018-42-2,8070-53-9
• Molecular Formula: C2H6OS
• Molecular Weight: 78.135
• Hs Code.: 29309070
• European Community (EC) Number: 200-664-3
• ICSC Number: 0459
• NSC Number: 760436,763
• UN Number: 2811,1993
• UNII: YOW8V9698H
• DSSTox Substance ID: DTXSID2021735
• Nikkaji Number: J1.130.885F,J1.933J
• Wikipedia: Dimethyl sulfoxide
• Wikidata: Q407927
• NCI Thesaurus Code: C437
• RXCUI: 3455
• Metabolomics Workbench ID: 38047
• ChEMBL ID: CHEMBL504
• Mol file: 67-68-5.mol

Synonyms:Methane,sulfinylbis- (9CI);Methyl sulfoxide (8CI);DMS 70;DMS 90;DMSO;Demavet;Demeso;Demsodrox;Dimethyl sulphoxide;Dimethylsulfoxide;Dimexide;Dimexidum;Dipirartril-tropico;Dolicur;Domoso;Dromisol;Durasorb;Gamasol 90;Herpid;Hyadur;Infiltrina;Kemsol;NSC 763;Rimso 50;SQ 9453;Sclerosol;Somipront;Sulfinylbismethane;Syntexan;Methyl Sulfoxide;

Chemical Property of Dimethyl sulphoxide

Chemical Property:

• Appearance/Colour: colorless liquid
• Melting Point: 18.4 °C
• Refractive Index: n20/D 1.479(lit.)
• Boiling Point: 189 °C at 760 mmHg
• Flash Point: 85 °C
• PSA: 36.28000
• Density: 1.1 g/cm³
• LogP: 0.86040
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 78.01393598
• Heavy Atom Count: 4
• Complexity: 29
• Transport DOT Label: Poison

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S26:; S37/39:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Other Solvents
• Canonical SMILES: CS(=O)C
• Recent ClinicalTrials: Bladder Capacity as Objective Measure of Intravesical Treatment of Newly Diagnosed IC
• Recent EU Clinical Trials: Phase III, randomized, open-label, multicenter evaluation of efficacy and tolerability `of Ialuril (sodium hyaluronate-chondroitin sulfate) vs. dimethyl sulfoxide (DMSO) in women with interstitial cystitis / painful bladder syndrome (IC / BPS)
• Recent NIPH Clinical Trials: Phase III study of KRP-116D
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin. Exposure to high concentrations could cause lowering of consciousness. May accelerate skin absorption of other materials.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. The substance may have effects on the liver and blood. This may result in impaired functions and lesions of blood cells.
• History and Use: Dimethyl Sulfoxide (DMSO) has a long history of use as a polar solvent and active pharmaceutical ingredient. It is widely used for its excellent solvent properties.
• Chemical Structure and Decomposition: DMSO can decompose autocatalytically, with the chemical structure and function of the autocatalyst still under debate.; Thermal decomposition of DMSO produces several organic and inorganic acids, with DMSO acting as both an oxidizer and a reactant in their formation.; The presence of acids generated in situ serves as autocatalysts for the thermal decomposition of DMSO.
• Environmental Friendliness and Safety: DMSO is considered more environmentally friendly and harmless to the human body compared to N, N-dimethylformamide (DMF). It is classified as class 3 (nontoxic) by regulatory authorities like the United States Food and Drug Administration (FDA) and the International Council for Harmonisation of Technical Requirements for Pharmaceuticals for Human Use (ICH).
• Applications: DMSO is widely used as a nonaqueous solvent, particularly in the life sciences, where it serves as a vehicle for hydrophobic compounds and as a cryoprotectant for cell storage. Its high complexation ability and solubility make it suitable for various applications, including in perovskite solutions.
• Toxicity and Effects on Cells: Despite its widespread use, DMSO is somewhat toxic and can affect cell behaviors in various ways.; Mechanistically, DMSO binds to proteins in the cytoplasm or nucleus, disrupting their functions and potentially leading to apoptosis.; While indispensable, DMSO is not without its drawbacks and should be used with caution in biological applications.

Technology Process of Dimethyl sulphoxide

There total 211 articles about Dimethyl sulphoxide 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: 100.0%

Sodium trans-Bis(dimethhyl sulfoxide) tetrachlororuthenate(III) (131759-88-1,61779-28-0) → mer,cis-{RuCl3(2O)2(DMSO)} (131759-93-8) + dimethyl sulfoxide (67-68-5,8070-53-9)

Guidance literature:

With HClO₄; H₂O; In water; byproducts: chlorode ion; Reaction was performed at pH=1 and temp. 35°C.; Kinetics;

Reference yield: 94.0%

dimethylbromosulphonium bromide (50450-21-0) + Benzaldoxime (932-90-1) → dimethyl sulfoxide (67-68-5,8070-53-9) + benzonitrile (100-47-0)

Guidance literature:

In acetonitrile; at 20 ℃; for 5.5h;

DOI:10.1016/j.tetlet.2009.07.100

Reference yield: 92.0%

dimethylsulfide (75-18-3) → dimethylsulfone (67-71-0) + dimethyl sulfoxide (67-68-5,8070-53-9)

Guidance literature:

With C₃₀H₂₄N₂O₇W; dihydrogen peroxide; In dichloromethane; water; for 1h; Reflux;

DOI:10.1002/ejic.200701043

upstream raw materials:

dimethylsulfide

trimethylsulfoxonium iodide

S,S-dimethylsulfodiimide

3,4-dihydroisoquinoline 1,2-oxide

Downstream raw materials:

benzoyloxy-methylsulfanyl-methane

N,N-diphenylurea

bis(diphenyl)urea

N-(dimethyl(oxo)-λ6-sulfanylidene)benzenesulfonamide

Refernces

• 1、 Addison,Sheldon. "-". . p. 2705,2708. Retrieved 1956.
• 2、 Krishnan, V.,Patel, C. C.. "". . p. 2201 - 2206. Retrieved 1964.
• 3、 Tevault, D. E.,Mowery, R. L.,Smardzewski, R. R.. "Ozone and oxygen atom reactions with dimethylsulfide and methanethiol in argon matrices". . p. 4480 - 4487. Retrieved 1981.
• 4、 Bragante, Letanzio,Desmarteau, Darryl D.. "THE CHEMISTRY OF 3-TRIFLUOROMETHYL-PERFLUORO-AZA-2-BUTENE AND THE SYNTHESIS OF A NEW OXAZIRIDINE: 3,3-BISTRIFLUOROMETHYL-2-TRIFLUOROMETHYLOXAZIRIDINE". . p. 181 - 197. Retrieved 1991.
• 5、 Vayssie, Stephane,Elias, Horst. "Fast oxidation of organic sulfides by hydrogen peroxide by in situ generated peroxynitrous acid". . p. 2088 - 2090. Retrieved 1998.
• 6、 Adam, Waldemar,Mitchell, Catherine M.,Saha-Moeller, Chantu R.. "Chemoselective methyltrioxorhenium(VII)-catalyzed sulfoxidations with hydrogen peroxide". . p. 13121 - 13124. Retrieved 1994.
• 7、 Kargar, Hadi,Kaka-Naeini, Azar,Fallah-Mehrjardi, Mehdi,Behjatmanesh-Ardakani, Reza,Amiri Rudbari, Hadi,Munawar, Khurram Shahzad. "Oxovanadium and dioxomolybdenum complexes: synthesis, crystal structure, spectroscopic characterization and applications as homogeneous catalysts in sulfoxidation". . p. 1563 - 1583. Retrieved 2021/05/11.
• 8、 Yarmohammadi, Nasrin,Ghadermazi, Mohammad,Mozafari, Roya. "Copper based on diaminonaphthalene-coated magnetic nanoparticles as robust catalysts for catalytic oxidation reactions and C-S cross-coupling reactions". . p. 9366 - 9380. Retrieved 2021/03/16.