70-29-1

Basic information

• Product Name: DIETHYL SULFOXIDE
• Synonyms: diethylsulphoxide;Ethane, 1,1'-sulfinylbis-;Ethanesulfinyl-ethane;ethylsulfinylethane;ETHYLSULPHOXIDE;1-ethylsulfinylethane;ETHYL SULFOXIDE;DIETHYL SULFOXIDE
• CAS NO: 70-29-1
• Molecular Formula: C₄H₁₀OS
• Molecular Weight: 106.19
• EINECS: 200-732-2
• Mol File: 70-29-1.mol
• Article Data: 29

Chemical Properties

• Melting Point: 14°C
• Boiling Point: 169.15°C (rough estimate)
• Flash Point: 82°C
• Appearance: /liquid
• Density: 1.0092
• Vapor Pressure: 0.258mmHg at 25°C
• Refractive Index: 1.5920 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: DIETHYL SULFOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL SULFOXIDE(70-29-1)
• EPA Substance Registry System: DIETHYL SULFOXIDE(70-29-1)

Safety Data

• Hazardous Substances Data: 70-29-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 26, p. 253, 1996 DOI: 10.1080/00397919608003612

InChI:InChI=1/C4H10OS/c1-3-6(5)4-2/h3-4H2,1-2H3

Synthetic route

diethyl sulphide (352-93-2) → diethyl sulphide (70-29-1)

Conditions	Yield
With oxygen; isobutyraldehyde; tris(1,3-bis(p-methoxyphenyl)-1,3-propanedionato)nickel(II) In acetonitrile at 60℃; for 21h;	100%
With lithium perchlorate; Re(O)(2-(2'-hydroxyphenyl)-2-oxazoline)2Cl In [D3]acetonitrile; water-d2 at 20℃; for 4h;	100%
With dihydrogen peroxide In water; acetonitrile at 24.84℃; for 1.66667h;	100%

diethyl sulphide (352-93-2) + 2-Oxobutyric acid (600-18-0) → diethyl sulphide (70-29-1) + carbon dioxide (124-38-9) + propionic acid (802294-64-0)

Conditions	Yield
With oxygen; methylene blue In pyridine; acetonitrile for 2h; Irradiation;	A 100% B n/a C 52%

diethyl sulphide (352-93-2) + benzophenone oxide O-<1-hydroperoxy-3,3-(dimethoxycarbonyl)-1-phenyl-2-propenyl> ether (218794-58-2) → diethyl sulphide (70-29-1) + Benzophenone oxime (574-66-3) + methyl 2-carbomethoxy-4-methylphenyl-4-oxo-2-butenoate (64677-34-5)

Conditions	Yield
In tetrachloromethane for 0.5h; Product distribution;	A n/a B 98% C 97%

diethyl sulphide (352-93-2) + 2-oxopentanoic acid (1821-02-9) → diethyl sulphide (70-29-1) + carbon dioxide (124-38-9) + butyric acid (107-92-6)

Conditions	Yield
With oxygen; methylene blue In pyridine; acetonitrile for 2h; Irradiation;	A 92% B n/a C 19%

diethyl sulphide (352-93-2) + Benzoylformic acid (611-73-4) → diethyl sulphide (70-29-1) + diethylsulfone (597-35-3) + carbon dioxide (124-38-9) + benzoic acid (65-85-0)

Conditions	Yield
With oxygen; 5,15,10,20-tetraphenylporphyrin In benzene for 2h; Irradiation;	A 88% B 10% C n/a D 38%
With oxygen; 5,15,10,20-tetraphenylporphyrin In benzene for 2h; Mechanism; Irradiation; other solvents and sensitizer;	A 88% B 10% C n/a D 38%

diethyl sulphide (352-93-2) + 2-oxo-propionic acid (127-17-3) → diethyl sulphide (70-29-1) + diethylsulfone (597-35-3) + carbon dioxide (124-38-9) + acetic acid (64-19-7)

Conditions	Yield
With oxygen; methylene blue In pyridine; acetonitrile for 2h; Irradiation;	A 65% B 3% C n/a D 64%

ethylmagnesium bromide (925-90-6) + benzyl (2S,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxylate (499140-11-3) → diethyl sulphide (70-29-1) + (1R,2S)-2-{[(benzyloxy)carbonyl]amino}-1-phenylpropyl (S)-ethanesulfinate

Conditions	Yield
In dichloromethane at -78℃;	A n/a B 46%

ethylmagnesium bromide (925-90-6) + benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate (499140-12-4) → diethyl sulphide (70-29-1) + (1R,2S)-2-{[(benzyloxy)carbonyl]amino}-1-phenylpropyl (S)-ethanesulfinate

Conditions	Yield
In dichloromethane at -78℃;	A n/a B 46%

diethyl ether (60-29-7) + ethyl chlorosulfate (625-01-4) + ethylmagnesium bromide (925-90-6) → diethyl sulphide (352-93-2) + diethyl sulphide (70-29-1)

diethyl ether (60-29-7) + ethyl chlorosulfate (625-01-4) + ethylmagnesium bromide → diethyl sulphide (352-93-2) + diethyl sulphide (70-29-1)

ethyl chlorosulfate (625-01-4) + ethylmagnesium bromide (925-90-6) → diethyl sulphide (352-93-2) + diethyl sulphide (70-29-1)

Conditions	Yield
With diethyl ether Zersetzen mit Wasser und Essigsaeure;

furan (110-00-9) + ethylmagnesium bromide (925-90-6) + ethyl (2-bromo)phenyl sulfoxide (112921-53-6) → 1,4-dihydronaphthalene-1,4-epoxide (573-57-9) + diethyl sulphide (70-29-1)

Conditions	Yield
1.) THF, 60 deg C, 11 h; Yield given. Multistep reaction. Yields of byproduct given;

diethyl sulphide (352-93-2) + 3-(4-nitrophenyl)-2-(phenylsulfonyl)-1,2-oxaziridine (86428-23-1, 78377-89-6) → diethyl sulphide (70-29-1)

Conditions	Yield
In chloroform-d1 Kinetics; Competition Oxidation Rate;

diethyl sulphide (352-93-2) + potassium N-bromo-p-toluenesulfonamide (70284-20-7) → diethyl sulphide (70-29-1) + S,S-Diethyl-N-p-tolylsulfonylsulfilimin (13553-69-0) + toluene-4-sulfonamide (70-55-3)

Conditions	Yield
With Britton-Robinson buffer In methanol; water at 20℃; Rate constant; Mechanism; Product distribution; NaOH, pH = 12.70; also in unbuffered solution;

diethyl sulphide (352-93-2) → diethyl sulphide (70-29-1) + diethylsulfone (597-35-3)

Conditions	Yield
With oxygen; 5,10,15,20-tetrakisphenylporphyrin In tetrahydrofuran at -39℃; for 1.08333h; Product distribution; Irradiation; photositised oxygenation of further cyclic and acyclic sulfides;
With oxygen; rose bengal In acetone at 23 - 24℃; Kinetics; Rate constant; Irradiation; other solvents, other temperature;
With molecular sieve; dihydrogen peroxide In acetone for 90h; Product distribution; Heating; other thioethers; var. reaction times and temp.;

di-p-tolylsulfur diimide (3839-88-1, 57083-05-3, 57083-06-4) → diethyl ether (60-29-7) + diethyl sulphide (70-29-1) + p-toluidine (106-49-0)

Conditions	Yield
With ethanol; copper dichloride at 22℃; Rate constant; further catalysts; pseudo-first-order rate constants for ethanolysis reactions;

diphenylsulfur diimide (3839-89-2, 66085-13-0, 66085-14-1, 66085-15-2) → diethyl ether (60-29-7) + diethyl sulphide (70-29-1) + aniline (62-53-3)

Conditions	Yield
With ethanol; copper dichloride at 22℃; Rate constant; pseudo-first-order rate constants for ethanolysis reactions;

bis(p-chlorophenyl)sulfur diimide (2648-43-3, 57083-07-5, 57155-78-9) → diethyl ether (60-29-7) + diethyl sulphide (70-29-1) + 4-chloro-aniline (106-47-8)

Conditions	Yield
With ethanol; copper dichloride at 22℃; Rate constant; pseudo-first-order rate constants for ethanolysis reactions;

N,N'-dip-bromophenylsulfodiimide (3839-86-9) → diethyl ether (60-29-7) + diethyl sulphide (70-29-1) + 4-bromo-aniline (106-40-1)

Conditions	Yield
With ethanol; copper dichloride at 22℃; Rate constant; pseudo-first-order rate constants for ethanolysis reactions;

1,3-bis(p-nitrophenyl)-2-thia-1,3-diazaallene (15148-19-3) → diethyl ether (60-29-7) + diethyl sulphide (70-29-1) + 4-nitro-aniline (100-01-6)

Conditions	Yield
With ethanol; copper dichloride at 22℃; Rate constant; pseudo-first-order rate constants for ethanolysis reactions;

N,N'-bis-(3-nitro-phenyl)-sulfur diimide (17426-08-3) → diethyl ether (60-29-7) + diethyl sulphide (70-29-1) + 3-nitro-aniline (99-09-2)

Conditions	Yield
With ethanol; copper dichloride at 22℃; Rate constant; pseudo-first-order rate constants for ethanolysis reactions;

4,4'-(λ4-sulfanediylidenediamino)-bis-benzoic acid diethyl ester (23721-53-1) → diethyl ether (60-29-7) + diethyl sulphide (70-29-1) + p-aminoethylbenzoate (94-09-7)

Conditions	Yield
With ethanol; copper dichloride at 22℃; Rate constant; pseudo-first-order rate constants for ethanolysis reactions;

N,N'-di-m-tolyl-sulfur diimide (19349-01-0) → diethyl ether (60-29-7) + diethyl sulphide (70-29-1) + 1-amino-3-methylbenzene (108-44-1)

Conditions	Yield
With ethanol; copper dichloride at 22℃; Rate constant; pseudo-first-order rate constants for ethanolysis reactions;

diethyl sulfoxide radical cation (70-29-1) → diethyl sulphide (70-29-1)

Conditions	Yield
With hydrogenchloride In water at 18℃; Equilibrium constant; Irradiation;

C12H8Cl2N2S → diethyl ether (60-29-7) + diethyl sulphide (70-29-1) + 3-chloro-aniline (108-42-9)

Conditions	Yield
With ethanol; copper dichloride at 22℃; Rate constant; pseudo-first-order rate constants for ethanolysis reactions;

3-acetyl-2-methoxy-5-phenylfuran (59624-45-2) → diethyl sulphide (70-29-1) + methyl (Z)-2-acetyl-3-benzoylacrylate (75519-88-9)

Conditions	Yield
With methanol; diethyl sulphide; oxygen; methylene blue 1.) irradiation, 2.) CCl4, 10 min; Yield given. Multistep reaction;

diethyl sulphide (352-93-2) → diethyl sulphide (70-29-1) + (E)-2-benzoylbut-2-enedioic acid dimethyl ester (6237-61-2)

Conditions	Yield
With methanol; oxygen; methylene blue; methyl 2-methoxy-5-phenyl-furan-4-carboxylate 1.) irradiation, 2.) MeOH, 15 min; Yield given. Multistep reaction;

methyl 2-methoxy-5-phenyl-furan-3-carboxylate (115852-13-6) → diethyl sulphide (70-29-1) + methyl 2-carbomethoxy-4-methylphenyl-4-oxo-2-butenoate (64677-34-5)

Conditions	Yield
With methanol; diethyl sulphide; oxygen; methylene blue 1.) irradiation, 2.) methanol, 30 min; Yield given. Multistep reaction;

dihydrogen hexachloroplatinate(IV) hexahydrate + diethyl sulphide (70-29-1) + tetraethylammonium chloride → tetraethylammonium diethylsulfoxidopentachloroplatinate

Conditions	Yield
In acetonitrile	93%

diethyl sulphide (70-29-1) → diethyl sulphide (352-93-2)

Conditions	Yield
With 1,4-dibromo-butane; zinc at 80℃; for 0.5h;	90%
With hexamethyldisilathiane In dichloromethane at 60℃; for 6h;	87%
durch Penicillium brevicaule;
With sodium hydroxide; chloroform; tetrabutyl-ammonium chloride In chloroform at 25℃; Mechanism; var. times;
With triethylsilane; dihydrogen hexachloroplatinate at 150℃; for 40h; Product distribution; Ni catalysts, oth. reagent;

diethyl sulphide (70-29-1) → diethylsulfone (597-35-3)

Conditions	Yield
With potassium superoxide; 2-Nitrobenzenesulfonyl chloride In acetonitrile at -30℃; for 5h;	89%
With dipotassium peroxodisulfate In water at 60℃; Kinetics; Thermodynamic data; Mechanism; further temperature; ΔE(excit), ΔS(excit); effect of oxygen and concentration on the rate;
bei der Oxydation;
With chloroform; ozone at 0℃;
With tetrachloromethane; ozone

dihydrogen hexachloroplatinate(IV) hexahydrate + diethyl sulphide (70-29-1) + ethyltriphenylphosphonium chloride (896-33-3) → triphenylethylphosphonium diethylsulfoxidopentachloroplatinate

Conditions	Yield
In acetonitrile	86%

potassium tetrachloroplatinate(II) (10025-99-7) + diethyl sulphide (70-29-1) → [Pt(diethyl sulphoxide)I2]2 (1044254-31-0, 72557-00-7)

Conditions	Yield
With potassium iodide In water treatment of K2PtCl4 with KI for 5 min, addn. of 1 equiv. sulfoxide (pptn.); filtration (after 30 min), washing (water), drying (vac., over CaCl2), dissoln. in CHCl3, filtration, evapn., washing (hexane), drying in air; elem. anal.;	85%

potassium hexabromoplatinate(IV) + tetraphenylstibonium bromide (16894-69-2, 21450-52-2) + diethyl sulphide (70-29-1) → 2C28H30OSSb(1+)*Br6Pt(2-)

Conditions	Yield
Stage #1: potassium hexabromoplatinate(IV); tetraphenylstibonium bromide In water Stage #2: diethyl sulphide	84%

bis(ruthenium(2,3,7,8,12,13,17,18-octaethylporphyrin)) (54762-43-5) + diethyl sulphide (70-29-1) → bis(diethyl sulfoxide)(octaethylporphyrinato)ruthenium(II) (164535-53-9)

Conditions	Yield
In dichloromethane N2 atmosphere; addn. of Et2SO soln. to Ru-complex; hexane addn., partial solvent removal, filtration, vol. reduction (pptn.), filtration off, drrying (vac., 70°C, overnight); elem. anal.;	80%

diethyl sulphide (70-29-1) + N-tert-butyl-α-phenylnitrone (3376-24-7) → N-tert-butyl-N-(1-phenyl-2-methyl-2-ethylsulfinyl) ethyl hydroxylamine

Conditions	Yield
Stage #1: diethyl sulphide With n-butyllithium In tetrahydrofuran Stage #2: N-tert-butyl-α-phenylnitrone In tetrahydrofuran at -78℃; for 2h;	76%

1,2,5-trimethyl-1H-pyrrole (930-87-0) + diethyl sulphide (70-29-1) → Diethyl-(1,2,5-trimethyl-1H-pyrrol-3-yl)-sulfonium; chloride

Conditions	Yield
With chloro-trimethyl-silane In acetonitrile Ambient temperature;	72%

diethyl sulphide (70-29-1) + 4-methyl-N-{2-(phenylethynyl)phenyl}benzenesulfonamide (442155-91-1) → 3-(ethylthio)-2-phenyl-1-tosyl-1H-indole

Conditions	Yield
With thionyl chloride at 0 - 70℃; for 10h;	72%

2-phenyl-1H-pyrrole (3042-22-6) + diethyl sulphide (70-29-1) → Diethyl-(5-phenyl-1H-pyrrol-2-yl)-sulfonium; chloride

Conditions	Yield
With chloro-trimethyl-silane In acetonitrile Ambient temperature;	71%

di-μ-chloro-dichlorobis(diethyl sulfoxide)diplatinum + diethyl sulphide (70-29-1) → trans-dichlorobis(diethyl sulfoxide)platinum(II) (66767-30-4)

Conditions	Yield
In dichloromethane to a soln. of (Pt2(Et2SO)2Cl4) in CH2Cl2 was added Et2SO in CH2Cl2 withstirring; the mixt. was cooled in ice and diethyl ether was added, solid was filtered off, washed with diethyl ether, air-dried; elem. anal.;	70%

diethyl sulphide (70-29-1) + 5-chloro-6H-anthra[1,9-cd]isoxazol-6-one (70730-92-6) → N-(4-chloro-9,10-dioxo-9,10-dihydroanthracen-1-yl)-S,S-diethylsulfoximide (1192657-31-0) + 1-amino-4-chloroanthraquinone (2872-47-1)

Conditions	Yield
In sulfolane at 130℃; for 2h;	A 70% B n/a

N-Methylpyrrole (96-54-8) + diethyl sulphide (70-29-1) → Diethyl-(1-methyl-1H-pyrrol-2-yl)-sulfonium; chloride

Conditions	Yield
With chloro-trimethyl-silane In acetonitrile Ambient temperature;	68%

diethyl sulphide (70-29-1) + hydrogen bromide (10035-10-6, 12258-64-9) + platinum (7440-06-4) → trans-tetrabromobis(diethyl sulfide) platinum(IV) (19525-76-9)

Conditions	Yield
In further solvent(s) heating of Pt, concd. HBr and diethyl sulfoxide on boiling water bath for 1 h; pptn., cooling, filtration, washing with water, drying in oven at 60°C;	68%

diethyl sulphide (70-29-1) + 6H-anthra<1,9-cd>isoxazol-6-one (70730-89-1) → N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-S,S-diethylsulfoximide (1192656-58-8) + 1-amino-9,10-anthracenedione (82-45-1)

Conditions	Yield
In sulfolane at 130℃; for 3h;	A 67% B n/a

diethyl sulphide (70-29-1) + potassium o-nitrobenzoate (15163-59-4) → 1-ethylsulfanyl-2-nitrobenzene (3058-46-6)

Conditions	Yield
With 1,10-Phenanthroline; zinc trifluoromethanesulfonate; copper(I) bromide at 150℃; for 24h; Molecular sieve;	67%

2,5-dimethyl-1-phenyl-1H-pyrrole (83-24-9) + diethyl sulphide (70-29-1) → 3-Chloro-2,5-dimethyl-1-phenyl-1H-pyrrole + (2,5-Dimethyl-1-phenyl-1H-pyrrol-3-yl)-diethyl-sulfonium; chloride

Conditions	Yield
With chloro-trimethyl-silane In acetonitrile Ambient temperature;	A 15% B 66%

diethyl sulphide (70-29-1) + N-tert-butyl-α-tert-butyl nitrone (72331-68-1) → N-tert-butyl-N-(1-tert-butyl-2-ethylsulfinyl)propylhydroxylamine (412929-83-0)

Conditions	Yield
Stage #1: diethyl sulphide With n-butyllithium In tetrahydrofuran at -20℃; Stage #2: N-tert-butyl-α-tert-butyl nitrone In tetrahydrofuran at -78℃; for 4h;	66%

pyrrole (109-97-7) + diethyl sulphide (70-29-1) → Diethyl-(1H-pyrrol-2-yl)-sulfonium; chloride

Conditions	Yield
With chloro-trimethyl-silane In acetonitrile Ambient temperature;	65%

styrene (292638-84-7) + diethyl sulphide (70-29-1) → 2-(ethylsulfonyl)-1-phenylethan-1-one (77970-53-7)

Conditions	Yield
With iron(III) chloride; oxygen; hydrazine hydrate at 40℃; for 36h;	65%

diethyl sulphide (70-29-1) + benzoyl chloride (98-88-4) → 1-(ethylthio)ethyl benzoate (91970-36-4)

Conditions	Yield
With iron(III) oxide; triethylamine In toluene at 20℃; for 2h; Pummerer Sulfoxide Rearrangement; Inert atmosphere; regioselective reaction;	65%
With triethylamine In toluene at 20℃; for 2h; Inert atmosphere;	65%

Upstream product

• 352-93-2 diethyl sulphide 
• 17426-08-3 N,N'-bis-(3-nitro-phenyl)-sulfur diimide 
• 135462-61-2 methyl 2-methoxy-4-methyl-5-phenyl-furan-3-carboxylate 
• 3839-86-9 bis(p-bromophenyl)sulfur diimide 
• 2648-43-3 bis(p-chlorophenyl)sulfur diimide 
• 70284-20-7 N-bromo-N-potassio-p-toluenesulfonamide 
• 86428-23-1 3-(4-nitrophenyl)-2-(phenylsulfonyl)-1,2-oxaziridine 
• 600-18-0 2-Oxobutyric acid 
• 110-00-9 furan 
• 925-90-6 ethylmagnesium bromide 
• 112921-53-6 ethyl (2-bromo)phenyl sulfoxide 
• 3839-89-2 diphenylsulfur diimide 
• 557-20-0 diethylzinc 
• 499140-12-4 benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate 

Downstream Products

• 64096-98-6 4-(1,1-dimethylethyl)-2-(ethylthio)phenol 
• 3031-74-1 ethyl hydroperoxide 
• 628-37-5 diethyl peroxide 
• 629-19-6 C₆H₁₄S₂⁽¹⁺⁾ 
• 597-35-3 diethylsulfone 
• 75-00-3 chloroethane 
• 10034-85-2 hydrogen iodide 
• 1219699-61-2 2-(2-ethylthio)-4-methylphenylpyridine 
• 108378-98-9 2-methyl-3-(toluene-4-sulfonyl)chroman-4-one 
• 108378-98-9 rac-(2S,3S)-2-methyl-3-(toluene-4-sulfonyl)chroman-4-one 
• 1769-24-0 2-methyl-4-quinazolone 
• 72-44-6 methaqualone 
• 3058-46-6 1-ethylsulfanyl-2-nitrobenzene 

Relevant articles and documents

PHOTOCHEMICAL RESTITUTION OF THE RADIOTHERMAL LUMINESCENCE PEAK IN DIETHYL SULFOXIDE

-

A novel binuclear iron(III)-salicylaldazine complex; synthesis, X-ray structure and catalytic activity in sulfide oxidation

A novel binuclear iron(III)-salicylaldazine complex has been synthesized and characterized by various techniques such as IR and UV–Vis spectroscopy and X-ray crystallography. The catalytic oxidation of sulfides in the presence of the aforementioned complex was explored at room temperature using urea hydrogen peroxide (UHP) as an oxidant. Effects of different reaction conditions consisting catalyst and oxidant amount, solvent effect and reaction time on the catalytic activity and selectivity in the reaction of methylphenylsulfide oxidation has been surveyed. Perfect selectivity toward sulfoxide was achieved after 15 min in CH3CN by choice of a properly optimized reaction condition.

Generation of VBr? VBi? VO?? defect clusters for 1O2 production for molecular oxygen activation in photocatalysis

Defect engineering on a semiconductor surface can provide coordinatively unsaturated sites for molecular oxygen activation in photocatalysis. In this work, we demonstrated that the vacancy type was key to modulate the molecular oxygen activation process on BiOBr nanosheets. By regulating the reaction time, an oxygen vacancy (VO??), a double atom defect cluster (VBi? VO??) and triple atom clusters (VBi? VO?? VBi? and VBr? VBi? VO??) were accordingly generated on the surface, subsurface and bulk of BiOBr. More importantly, the newly-discovered VBr? VBi? VO?? defect cluster was highly related to the singlet oxygen (1O2) production ability of BiOBr. Meanwhile, the excellent photocatalytic selective oxidation reactions were successfully realized over BiOBr with the VBr? VBi? VO?? defect cluster. In addition, time-dependent defect cluster generation and the associated molecular oxygen activation were discussed.