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Basic Information

Molecular Structure:
CAS No.:	67-68-5
Name:	Dimethyl sulphoxide
Article Data:	171

Formula:	C₂H₆OS
Molecular Weight:	78.135
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;
EINECS:	200-664-3
Density:	1.1 g/cm³
Melting Point:	18.4 °C
Boiling Point:	189 °C at 760 mmHg
Flash Point:	85 °C
Appearance:	colorless liquid
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	24/25-37/39-26-36-23
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

Raw Materials

934-72-5

103-81-1

519-73-3

Downstream Products

579-75-9

91-63-4

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Chemistry

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

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.

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.

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

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.

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

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.

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