Dimethyl sulfoxide supplier

Name
Dimethyl sulphoxide
EINECS 200-664-3
CAS No. 67-68-5
Article Data171
CAS DataBase
Density 1.1 g/cm³
Solubility
Melting Point 18.4 °C
Formula C₂H₆OS
Boiling Point 189 °C at 760 mmHg
Molecular Weight 78.135
Flash Point 85 °C
Transport Information
Appearance colorless liquid
Safety 24/25-37/39-26-36-23
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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;
PSA 36.28000
LogP 0.86040

Synthetic route

: 75-18-3
dimethylsulfide

: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
With Fe(AAEMA)3; oxygen; isovaleraldehyde In 1,2-dichloro-ethane under 760 Torr; for 20h; Ambient temperature;	100%
With lithium perchlorate; Re(O)(2-(2'-hydroxyphenyl)-2-oxazoline)2Cl In [D3]acetonitrile; water-d2 at 20℃; for 4h;	100%
With C12H11Cl3N2O3 In chloroform for 7h; Reflux;	100%

: 1520-31-6
dimethylsulfoximine

: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
With tert.-butylnitrite In chloroform at 25℃; for 0.166667h;	100%
With p-TolSO2NO In acetonitrile at 35℃; further solvents, reagents, sulfoximides;

: 131759-88-1, 61779-28-0
Sodium trans-Bis(dimethhyl sulfoxide) tetrachlororuthenate(III)

: 131759-93-8
mer,cis-{RuCl3(2O)2(DMSO)}

B: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
With HClO4; H2O In water Kinetics; byproducts: chlorode ion; Reaction was performed at pH=1 and temp. 35°C.;	A 100% B 100%

: 59091-96-2, 89395-66-4, 90698-13-8, 194497-67-1, 482618-33-7, 41290-68-0, 72904-47-3, 61779-29-1, 64376-67-6, 75766-08-4
dichlorotetrakis(dimethylsulfoxide)ruthenium

: 40169-66-2
triars

A: 112220-32-3
RuCl2(OS(CH3)2)(CH3C(CH2As(C6H5)2)3)

B: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
In toluene Ar atmosphere, heating (80°C, 10 min, 90°C, overnight), pptn.; washing of ppt. (toluene, Et2O), drying; elem. anal.;	A 96% B n/a

...Expand

: 50450-21-0
dimethylbromosulphonium bromide

: 39201-89-3
3,4,5-trimethoxybenzaldehyde oxime

A: 67-68-5
dimethyl sulfoxide

B: 1885-35-4
3,4,5-trimethoxybenzonitrile

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 3h;	A n/a B 96%

...Expand

: 76-05-1
trifluoroacetic acid

: S,S-dimethyl-4-methylanilinosulfonium picrate

A: 350-96-9
2,2,2-trifluoro-N-(4-methylphenyl)acetamide

B: 106-49-0
p-toluidine

C: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
at 50℃; for 5h; Elimination; acylation; retro-Pummerer reaction;	A 3% B 95% C 67%

...Expand

: 75-18-3
dimethylsulfide

A: 67-71-0
dimethylsulfone

B: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
With C30H24N2O7W; dihydrogen peroxide In dichloromethane; water for 1h; Reflux;	A 94% B 6%
With dihydrogen peroxide In ethanol; hexane; water at 60℃; for 0.0833333h;	A 92% B 6%
With dihydrogen peroxide In water at 30 - 35℃; for 24h; Sealed tube; Green chemistry;	A 62% B 68%

: 1521-41-1
veratramide

: 50450-21-0
dimethylbromosulphonium bromide

A: 2024-83-1
veratronitrile

B: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
In acetonitrile for 2h; Reflux;	A 94% B n/a

...Expand

: 50450-21-0
dimethylbromosulphonium bromide

: 932-90-1
Benzaldoxime

A: 67-68-5
dimethyl sulfoxide

B: 100-47-0
benzonitrile

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 5.5h;	A n/a B 94%

...Expand

: Benzoyl(4-chlorbenzoyl)(dimethylsulfonio)methanid

A: 54458-32-1
1-(4-chlorophenyl)-3-phenylpropane-1,2,3-trione

B: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
With ozone 1) CH2Cl2, -78 deg C, 2) Et2O, H2O;	A 93% B n/a

: (η5-pentamethylcyclopentadienyl)(CPhCHCOO)(Me2SO)rhodium

A: (η5-pentamethylcyclopentadienyl)(CPhCHCOOMe)Irhodium

B: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
With methyl iodide In toluene N2 atmosphere; stirring (2-15 h, 60°C); elem. anal.;	A 92% B n/a

: 50450-21-0
dimethylbromosulphonium bromide

: 1129-37-9
4-nitrobenzaldehyde oxime

A: 67-68-5
dimethyl sulfoxide

B: 619-72-7
4-nitrobenzonitrile

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 6h;	A n/a B 92%

...Expand

: Bis(4-chlorbenzoyl)(dimethylsulfonio)methanid

A: 29574-62-7
1,3-bis(4-chlorophenyl)propane-1,2,3-trione

B: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
With ozone 1) CH2Cl2, -78 deg C, 2) Et2O, H2O;	A 91% B n/a

: 75-18-3
dimethylsulfide

: cis-[Ru(1,4,7-trimethyl-1,4,7-triazacyclononane)O2(trifluoroacetate)]ClO4

: 75-05-8
acetonitrile

A: [(1,4,7-trimethyl-1,4,7-triazacyclononane)(CF3CO2)Ru(II)(CH3CN)2]ClO4

B: 67-71-0
dimethylsulfone

C: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
In acetonitrile Me2S reacted with Ru-compound in degassed acetonitrile;	A n/a B 9% C 91%

...Expand

: 3717-21-3, 3717-22-4, 140461-28-5, 140461-29-6, 3235-04-9
p-methoxyl benzaldoxime

: 50450-21-0
dimethylbromosulphonium bromide

A: 67-68-5
dimethyl sulfoxide

B: 874-90-8
4-methoxybenzonitrile

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 4h;	A n/a B 91%

...Expand

: 55-21-0
benzamide

: 50450-21-0
dimethylbromosulphonium bromide

A: 67-68-5
dimethyl sulfoxide

B: 100-47-0
benzonitrile

Conditions

Conditions	Yield
In acetonitrile for 2h; Reflux;	A n/a B 91%

...Expand

: 112220-39-0
[bis(dimethylsulfoxide-O)(triphos)aquaruthenium(II)] triflate

A: 112220-44-7
Ru(CF3SO3)(CO)2(CH3C(CH2P(C6H5)2)3)(1+)*CF3SO3(1-)={Ru(CF3SO3)(CO)2(CH3C(CH2P(C6H5)2)3)}(CF3SO3)

B: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
With CO In dichloromethane byproducts: H2O; stirring of soln. under CO atmosphere (15 min); pptn. (Et2O addn.), washing (Et2O), drying; elem. anal.;	A 90% B n/a

: 50450-21-0
dimethylbromosulphonium bromide

: 59336-59-3
cinnamaldehyde oxime

A: 1885-38-7
cinnamic nitrile

B: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 3h;	A 90% B n/a

...Expand

: 50450-21-0
dimethylbromosulphonium bromide

: 619-80-7
4-nitrobenzamide

A: 67-68-5
dimethyl sulfoxide

B: 619-72-7
4-nitrobenzonitrile

Conditions

Conditions	Yield
In acetonitrile for 4h; Reflux;	A n/a B 90%

...Expand

: 50450-21-0
dimethylbromosulphonium bromide

: 3848-36-0
4-chlorobenzaldoxime

A: 623-03-0
4-Cyanochlorobenzene

B: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 5h;	A 89% B n/a

...Expand

: 50450-21-0
dimethylbromosulphonium bromide

: 619-56-7
4-chlorobenzamide

A: 623-03-0
4-Cyanochlorobenzene

B: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
In acetonitrile for 3h; Reflux;	A 89% B n/a

...Expand

: 34025-26-8
2-(dimethyl-λ4-sulfaneylidene)-1,3-diphenylpropane-1,3-dione

A: 643-75-4
1,3-diphenyl-propane-1,2,3-trione

B: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
With ozone 1) CH2Cl2, -78 deg C, 2) Et2O, H2O;	A 88% B n/a

: 3235-02-7, 3717-15-5, 3717-16-6, 140461-26-3, 140461-27-4
p-methylbenzaldehyde oxime

: 50450-21-0
dimethylbromosulphonium bromide

A: 67-68-5
dimethyl sulfoxide

B: 104-85-8
para-methylbenzonitrile

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 4h;	A n/a B 88%

...Expand

: 75-18-3
dimethylsulfide

: C96H104MnN7O(1+)*Cl6Sb(1-)

A: C96H104MnN7(1+)*Cl6Sb(1-)

B: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
In dichloromethane at 25℃; Inert atmosphere;	A n/a B 88%

...Expand

: 112220-37-8
Ru(OS(CH3)2)3(CH3C(CH2As(C6H5)2)3)(2+)*2CF3SO3(1-)={Ru(OS(CH3)2)3(CH3C(CH2As(C6H5)2)3)}(CF3SO3)2

A: 112220-46-9
Ru(CF3SO3)(CO)2(CH3C(CH2As(C6H5)2)3)(1+)*CF3SO3(1-)={Ru(CF3SO3)(CO)2(CH3C(CH2As(C6H5)2)3)}(CF3SO3)

B: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
With CO In dichloromethane stirring of soln. under CO atmosphere (3 h); pptn. (Et2O addn.), washing (Et2O), drying; elem. anal.;	A 87% B n/a

: (η5-pentamethylcyclopentadienyl)(CPhCHCOO)(Me2SO)iridium

A: (η5-pentamethylcyclopentadienyl)(CHCMeCOOMe)Iiridium

B: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
With methyl iodide In toluene N2 atmosphere; stirring (2-15 h, 60°C); elem. anal.;	A 87% B n/a

: 50450-21-0
dimethylbromosulphonium bromide

: 29683-84-9
thiophene-2-carbaldehyde oxime

A: 1003-31-2
thiophene-2-carbonitrile

B: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 3h;	A 87% B n/a

...Expand

: 50450-21-0
dimethylbromosulphonium bromide

: 629-01-6
n-octanamide

A: 124-12-9
caprylnitrile

B: 67-68-5
dimethyl sulfoxide

Conditions

Conditions	Yield
In acetonitrile for 4h; Reflux;	A 87% B n/a

...Expand

: 3424-93-9
4-methoxyphenylacetamide

: 50450-21-0
dimethylbromosulphonium bromide

A: 67-68-5
dimethyl sulfoxide

B: 874-90-8
4-methoxybenzonitrile

Conditions

Conditions	Yield
In acetonitrile for 2h; Reflux;	A n/a B 86%

...Expand

: 108-24-7
acetic anhydride

: 67-68-5
dimethyl sulfoxide

: 16437-69-7
(methylthio)methyl acetate

Conditions

Conditions	Yield
at 100℃; for 7h;	100%
	84%
With chloroform

: 67-68-5
dimethyl sulfoxide

: 67-71-0
dimethylsulfone

Conditions

Conditions	Yield
With sodium molybdate dihydrate; dihydrogen peroxide In methanol; water at 25℃; for 0.5h; Kinetics; Concentration;	100%
With iron(II) perchlorate monohydrate; ozone; acetonitrile	100%
With dihydrogen peroxide; [(η5-C5Me5)Mo(CO)3Cl] In acetonitrile at 35℃; for 2h;	99%

: 100-02-7
4-nitro-phenol

: 67-68-5
dimethyl sulfoxide

: 4527-37-1
1-<(methylthio)methoxy>-4-nitrobenzene

Conditions

Conditions	Yield
With t-butyl bromide; triethylamine at 35℃; for 24h;	100%

: 2175-90-8
6,6-Diphenylfulvene

: 67-68-5
dimethyl sulfoxide

: <5-(Diphenylmethylen)-1,3-cyclopentadien-1-yl>dimethylsulfonium-perchlorat

Conditions

Conditions	Yield
With lithium perchlorate; trifluoroacetic anhydride In dichloromethane -10 deg C to r.t.;	100%
With monoperchlorate; trifluoroacetic anhydride 1.) -10 deg C; Yield given. Multistep reaction;

: 17182-23-9
UC1023

: 67-68-5
dimethyl sulfoxide

: 82055-16-1
(20R)-20-(Methylthiomethoxy)-5α-pregnan-3β-ylacetat

Conditions

Conditions	Yield
With acetic anhydride In acetic acid for 96h; Ambient temperature;	100%

: 97135-48-3
(bis(diisopropylamino)phosphanyl)(trimethylsilyl)diazomethane

: 67-68-5
dimethyl sulfoxide

: 97135-52-9
C18H43N2OPSSi

Conditions

Conditions	Yield
In benzene Irradiation;	100%
In benzene for 8h; Ambient temperature; Irradiation; Yield given;
In benzene for 8h; Irradiation; Yield given;

: 85192-92-3
7-Nitro-anthra[1,9-cd]isoxazol-6-one

: 67-68-5
dimethyl sulfoxide

: 85193-01-7
1-S,S-dimethyl-N-(5-nitroanthraquinon-1-yl)sulfoximide

Conditions

Conditions	Yield
	100%

: 67-68-5
dimethyl sulfoxide

: 75-18-3
dimethylsulfide

Conditions

Conditions	Yield
With benzo[1,3,2]dioxaborole In benzene-d6 at 20℃; for 48h;	100%
With phenylsilane; dimanganese decacarbonyl In neat (no solvent) at 100℃;	96%
With sodium tetrahydroborate; iron(III) chloride In ethanol; water 1.) room temperature, 2 h, 2.) reflux, 5 - 10 min;	94%

: 67-68-5
dimethyl sulfoxide

: (3S)-2-(N-benzylamino)-3-(chloromethyl)valeronitrile

: (S)-2-(Benzyl-methylsulfanylmethyl-amino)-3-chloromethyl-pentanenitrile

Conditions

Conditions	Yield
With oxalyl dichloride In dichloromethane at -60℃; for 0.333333h;	100%

: 67-68-5
dimethyl sulfoxide

: 98-89-5
Cyclohexanecarboxylic acid

: 16437-72-2
(methylthio)methyl cyclohexanecarboxylate

Conditions

Conditions	Yield
With t-butyl bromide; sodium hydrogencarbonate at 35 - 45℃; for 13h; Esterification;	100%
With oxalyl dichloride; triethylamine In dichloromethane at -60 - 20℃; for 0.5h; Swern oxidation;	97%
With triethylamine at 160℃; for 20h; Schlenk technique; Inert atmosphere;	70%
With triethylamine at 160℃; under 760.051 Torr; for 20h; Pummerer Sulfoxide Rearrangement; Schlenk technique; Inert atmosphere; Green chemistry;	70%

: 67-68-5
dimethyl sulfoxide

: 223547-75-9
C32H50O7Si

: 170510-29-9
C34H54O7SSi

Conditions

Conditions	Yield
With acetic anhydride at 25℃; for 19h;	100%

: 109721-08-6
(S)-3-<(tert-butyldimethylsilyl)oxy>pentanedioic acid, monomethylester

: 67-68-5
dimethyl sulfoxide

: 205647-16-1
(3R)-[(tert-butyldimethylsilyl)oxy]-6-(methanesulfinyl)-5-oxohexanoic acid

Conditions

Conditions	Yield
Stage #1: dimethyl sulfoxide With n-butyllithium In tetrahydrofuran; hexane at -30 - 2℃; for 0.666667h; Metallation; Stage #2: (S)-3-<(tert-butyldimethylsilyl)oxy>pentanedioic acid, monomethylester In tetrahydrofuran; hexane at -66 - -30℃; for 0.916667h; Acylation;	100%

: Acetic acid (2R,3R,4R,5R)-2-((1S,2S,3R,4S,6R)-2-acetoxy-4,6-diazido-3-hydroxy-cyclohexyloxy)-5-acetoxymethyl-4-((2S,3S,4S,5S,6R)-4,5-diacetoxy-3-azido-6-azidomethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester

: 67-68-5
dimethyl sulfoxide

: Acetic acid (2R,3R,4R,5R)-2-((1S,2R,3R,4S,6R)-2-acetoxy-4,6-diazido-3-methylsulfanylmethoxy-cyclohexyloxy)-5-acetoxymethyl-4-((2S,3S,4S,5S,6R)-4,5-diacetoxy-3-azido-6-azidomethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester

Conditions

Conditions	Yield
With acetic anhydride; acetic acid at 20℃; for 48h; Pummerer rearrangement;	100%

: 112374-62-6
2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin-ruthenium(II)-carbonyl-dimethylsulfoxide

: 67-68-5
dimethyl sulfoxide

: 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin-ruthenium(II)-bis(dimethylsulfoxide)

Conditions

Conditions	Yield
In dimethyl sulfoxide Irradiation (UV/VIS); photolysis of a degassed or argon-bubbled DMSO soln. of the Ru complex;	100%

: 866596-13-6, 82621-20-3
5,10,15,20-tetraphenyl-21H,23H-porphyrin-ruthenium(II)-carbonyl-dimethylsulfoxide

: 67-68-5
dimethyl sulfoxide

: 5,10,15,20-tetraphenyl-21H,23H-porphyrin-ruthenium(II)-bis-dimethylsulfoxide

Conditions

Conditions	Yield
In dimethyl sulfoxide Irradiation (UV/VIS); photolyzing the Ru complex in a sealed degassed or argon-bubbled DMSO soln.;	100%

: 10025-99-7
potassium tetrachloroplatinate(II)

: 67-68-5
dimethyl sulfoxide

: dichlorobis(dimethyl sulfoxide)platinum(II)

Conditions

Conditions	Yield
In water for 2h;	100%
In water	91%
In water at 20℃;	90%

: 79-37-8
oxalyl dichloride

: 268234-15-7
3-(5-methoxymethoxy-2-methoxyphenyl)-3-propanol

: 67-68-5
dimethyl sulfoxide

: 268234-16-8
3-(5-methoxymethoxy-2-methoxyphenyl)-3-propanone

Conditions

Conditions	Yield
Stage #1: oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.25h; Stage #2: 3-(5-methoxymethoxy-2-methoxyphenyl)-3-propanol With triethylamine In dichloromethane at 20℃; for 1.33333h;	100%

...Expand

: bismuth trifluoride

: 4648-54-8
trimethylsilylazide

: 67-68-5
dimethyl sulfoxide

: bismuth triazide dimethylsulfoxide adduct

Conditions

Conditions	Yield
at 20℃; for 24h; Inert atmosphere;	100%

...Expand

: 67-68-5
dimethyl sulfoxide

: rac-5-({p-[2-(5-ethylpyridin-2-yl)-2-oxoethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

: PNU-91325

Conditions

Conditions	Yield
With phosphorus pentoxide In dichloromethane at 20℃; for 24h;	100%

: 2314-97-8
iodotrifluoromethane

: 67-68-5
dimethyl sulfoxide

: Ritter's trifluoroiodomethane-DMSO complex

Conditions

Conditions	Yield
at -78 - 23℃; Schlenk technique; Inert atmosphere;	100%
at -78 - 23℃; Inert atmosphere;	100%
at -78℃;

: 10025-99-7
potassium tetrachloroplatinate(II)

: ([1-benzyl-3-methyl]imidazolyl-2-ene)silver(I) bromide

: 67-68-5
dimethyl sulfoxide

: cis-(1-methyl-3-benzylimidazol-2-ylidene)PtBr2(DMSO)

Conditions

Conditions	Yield
at 60℃; for 24h;	100%

...Expand

: 2-(3′,4′-dihydroxyphenyl)-2,3-dihydro-4,6-dihydroxy-2-(methoxy)-3-benzo furanone

: 67-68-5
dimethyl sulfoxide

: 2-(3′,4′-dimethoxyphenyl)-2,3-dihydro-4,6-dimethoxy-2-(methoxy)-3-benzofuranone

Conditions

Conditions	Yield
Stage #1: 2-(3′,4′-dihydroxyphenyl)-2,3-dihydro-4,6-dihydroxy-2-(methoxy)-3-benzo furanone With potassium carbonate In acetone at 58℃; for 0.5h; Stage #2: dimethyl sulfoxide at 58℃; for 60h;	99.6%

: 67825-24-5
[magnesium(2,6-di-tert-butyl-4-methylphenolate)2(tetrahydrofuran)2]

: 67-68-5
dimethyl sulfoxide

: [magnesium(2,6-di-tert-butyl-4-methylphenolate)2(dimethylsulfoxide)2]

Conditions

Conditions	Yield
In toluene for 0.05h; Inert atmosphere; Glovebox;	99.5%

: 67-68-5
dimethyl sulfoxide

: 14431-67-5
(-)-mutilone

: 113323-23-2
(3aS,4R,6S,8R,9R,9aR,10R)-hexahydro-4,6,9,10-tetramethyl-<(methylthio)methoxy>-6-vinyl-3a,9-propano-3aH-cyclopentacyclooctene-1,5(4H,6H)-dione

Conditions

Conditions	Yield
With acetic anhydride In acetic acid Ambient temperature;	99%

: 67-68-5
dimethyl sulfoxide

: 93-07-2
Veratric acid

: 33838-03-8
(methylthio)methyl 3,4-dimethoxybenzoate

Conditions

Conditions	Yield
With oxalyl dichloride; triethylamine In dichloromethane at -60 - 20℃; for 0.5h; Swern oxidation;	99%
for 0.166667h; Microwave irradiation; Sealed vessel;	94%

: 555-16-8
4-nitrobenzaldehdye

: 67-68-5
dimethyl sulfoxide

: 60-24-2
2-hydroxyethanethiol

: 13458-01-0
2-hydroxyethyl 4-methoxycarbonylphenyl sulfide

Conditions

Conditions	Yield
With caesium carbonate at 25℃; for 0.75h;	99%

...Expand

: 868784-06-9
(4E,8E)-(R)-2-Hydroxy-2,5,9-trimethyl-11-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-undeca-4,8-dienoic acid methyl ester

: 67-68-5
dimethyl sulfoxide

: 868784-07-0
(4E,8E)-(R)-2,5,9-Trimethyl-2-methylsulfanylmethoxy-11-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-undeca-4,8-dienoic acid methyl ester

Conditions

Conditions	Yield
With acetic anhydride at 23℃; for 24h;	99%

Dimethyl sulfoxide Chemical Properties

Molecular Structure:

IUPAC Name: methylsulfinylmethane
Empirical Formula: C₂H₆OS
Molecular Weight: 78.1334
H bond acceptors: 1
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: 36.28Å²
Index of Refraction: 1.479
Molar Refractivity: 20.17 cm³
Molar Volume: 71 cm³
Surface Tension: 43.6 dyne/cm
Density: 1.099 g/cm³
Flash Point: 85 °C
Enthalpy of Vaporization: 40.78 kJ/mol
Boiling Point: 189 °C at 760 mmHg
Vapour Pressure: 0.805 mmHg at 25°C
Melting point: 18.4 °C
InChI
InChI=1/C2H6OS/c1-4(2)3/h1-2H3
Smiles
S(C)(C)=O
EINECS: 200-664-3
Sensitive: Hygroscopic
Merck: 14,3259
BRN: 506008
Stability: Stable. Incompatible with a very wide range of materials, including acid chlorides, strong acids, strong oxidizing agents, strong reducing agents, phosphorus halides, moisture, copper wool + trichloroacetic acid. Reacts violently with a number of materials - consult a full data sheet before use. Hygroscopic.
Product Categories: Pharmaceutical Intermediates; Organics;Analytical Chemistry; Solvents for HPLC & Spectrophotometry; Solvents for Spectrophotometry; Sulfur Compounds (for Synthesis); Synthetic Organic Chemistry
Synonyms of Dimethyl sulfoxide (CAS NO.67-68-5): (CH₃)₂SO ; A 10846 ; Decap ; Deltan ; Demasorb ; Demavet ; Demeso ; DMSO

Dimethyl sulfoxide History

Dimethyl sulfoxide (CAS NO.67-68-5) was first synthesized in 1866 by the Russian scientist Alexander Zaytsev, who reported his findings in in 1867. Dimethyl sulfoxide is a by-product of kraft pulping, which produces dimethyl sulfide as a side product. Oxidation of dimethylsulfide with oxygen or nitrogen dioxide gives Dimethyl sulfoxide.

Dimethyl sulfoxide Uses

Dimethyl sulfoxide (CAS NO. 67-68-5) is an important polar aprotic solvent. It is widely used to strip photoresist in TFT-LCD 'flat panel' displays and advanced packaging applications (such as wafer-level packaging / solder bump patterning). It also used in biopresevation especially stem cell banking. It is predominantly used as a topical analgesic, a vehicle for topical application of pharmaceuticals, as an anti-inflammatory, and an antioxidant.

Dimethyl sulfoxide Production

Dimethyl sulfoxide (CAS NO.67-68-5) is a by-product of kraft pulping. The sulfide used as a nucleophile also attacks the methoxy groups of lignin, producing methanethiol and Dimethyl Sulfide, which is oxidized to DMSO. Suppliers of DMSO are Arkema, Toray or the Gaylord Chemical Corporation.
It reacts with methyl iodide to form a sulfoxonium salt [(CH3)3SO]I, which can be deprotonated with sodium hydride to form the sulfur ylide:
(CH₃)₂SO + CH₃I → [(CH₃)₃SO]I
[(CH₃)₂SO ]I + NaH → [(CH₃)₂CH₂SO + NaI + H₂

Dimethyl sulfoxide Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
bird - wild	LD50	oral	100mg/kg (100mg/kg)		Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
cat	LDLo	intravenous	200mg/kg (200mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)	Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 1571, 1978.
chicken	LD50	oral	12gm/kg (12000mg/kg)		Journal of Pharmacy and Pharmacology. Vol. 15, Pg. 688, 1963.
dog	LD50	intravenous	2500mg/kg (2500mg/kg)	CARDIAC: OTHER CHANGES KIDNEY, URETER, AND BLADDER: HEMATURIA KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Cancer Chemotherapy Reports. Vol. 31, Pg. 7, 1963.
dog	LD50	oral	> 10gm/kg (10000mg/kg)		Annals of the New York Academy of Sciences. Vol. 141, Pg. 96, 1967.
guinea pig	LDLo	intraperitoneal	> 5500mg/kg (5500mg/kg)		Journal of Pharmacy and Pharmacology. Vol. 15, Pg. 688, 1963.
guinea pig	LDLo	oral	> 11gm/kg (11000mg/kg)		Journal of Pharmacy and Pharmacology. Vol. 15, Pg. 688, 1963.
mammal (species unspecified)	LD50	oral	21400mg/kg (21400mg/kg)		Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 39(4), Pg. 86, 1974.
man	TDLo	intravenous	606mg/kg (606mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"	Lancet. Vol. 2, Pg. 1004, 1980.
mouse	LD50	intraperitoneal	2500mg/kg (2500mg/kg)		Russian Pharmacology and Toxicology Vol. 35, Pg. 300, 1972.
mouse	LD50	intravenous	3100mg/kg (3100mg/kg)	SENSE ORGANS AND SPECIAL SENSES: HEMORRHAGE: EYE SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE	Toxicology and Applied Pharmacology. Vol. 15, Pg. 74, 1969.
mouse	LD50	oral	7920mg/kg (7920mg/kg)		Chimica Therapeutica. Vol. 3, Pg. 10, 1968.
mouse	LD50	skin	50gm/kg (50000mg/kg)		Annals of the New York Academy of Sciences. Vol. 141, Pg. 96, 1967.
mouse	LD50	subcutaneous	14gm/kg (14000mg/kg)	BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES KIDNEY, URETER, AND BLADDER: HEMATURIA	Annals of the New York Academy of Sciences. Vol. 141, Pg. 96, 1967.
mouse	LD50	unreported	12gm/kg (12000mg/kg)		United States Patent Document. Vol. #4767763,
rat	LD50	intraperitoneal	8200mg/kg (8200mg/kg)		Food and Chemical Toxicology. Vol. 22, Pg. 665, 1984.
rat	LD50	intravenous	5360mg/kg (5360mg/kg)	BEHAVIORAL: TREMOR LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: MUSCLE WEAKNESS	Toxicology and Applied Pharmacology. Vol. 7, Pg. 104, 1965.
rat	LD50	oral	14500mg/kg (14500mg/kg)	SENSE ORGANS AND SPECIAL SENSES: HEMORRHAGE: EYE SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE	Toxicology and Applied Pharmacology. Vol. 15, Pg. 74, 1969.
rat	LD50	skin	40gm/kg (40000mg/kg)		Annals of the New York Academy of Sciences. Vol. 141, Pg. 96, 1967.
rat	LD50	subcutaneous	12gm/kg (12000mg/kg)	BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Arzneimittel-Forschung. Drug Research. Vol. 14, Pg. 1050, 1964.
rat	LD50	unreported	1300mg/kg (1300mg/kg)		National Technical Information Service. Vol. AD-A159-418,
women	TDLo	skin	1800mg/kg (1800mg/kg)	LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: CYANOSIS BLOOD: OTHER CHANGES	Veterinary and Human Toxicology. Vol. 40, Pg. 87, 1998.

Dimethyl sulfoxide Safety Profile

Hazard Codes of Dimethyl sulfoxide (CAS NO.67-68-5): Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-37/39-26-36-23
S24/25:Avoid contact with skin and eyes.
S37/39:Wear suitable gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S23:Do not breathe vapour.
WGK Germany: 1
RTECS: PV6210000
F: 3
HS Code: 29309070

Dimethyl sulfoxide Specification

Dimethyl sulfoxide with a CAS number of 67-68-5. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. It has a distinctive property of penetrating the skin very readily, so that one may taste it soon after it comes into contact with the skin. Its taste has been described as oyster- or garlic-like.
Chemical Stability of Dimethyl sulfoxide (CAS NO. 67-68-5): Stable under normal temperatures and pressures. Hygroscopic: absorbs moisture or water from the air.
Conditions to Avoid: Incompatible materials, exposure to moist air or water.
Dimethyl sulfoxide is incompatibilities with Other Materials Strong oxidizing agents, perchloric acid.
Hazardous decomposition products of Dimethyl sulfoxide are carbon monoxide, oxides of sulfur, carbon dioxide, formaldehyde.
Hazardous polymerization of Dimethyl sulfoxide will not occur.

Product Name

Dimethyl sulphoxide

Synthetic route

Dimethyl sulfoxide Chemical Properties

Dimethyl sulfoxide History

Dimethyl sulfoxide Uses

Dimethyl sulfoxide Production

Dimethyl sulfoxide Toxicity Data With Reference

Dimethyl sulfoxide Safety Profile

Dimethyl sulfoxide Specification

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