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67-68-5

Basic Information
CAS No.: 67-68-5
Name: Dimethyl sulfoxide
Article Data: 171
Cas Database
Molecular Structure:
Molecular Structure of 67-68-5 (Dimethyl sulfoxide)
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
Solubility: N/A
Appearance: colorless liquid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 24/25-37/39-26-36-23
Transport Information: N/A
PSA: 36.28000
LogP: 0.86040
Synthetic route
75-18-3

dimethylsulfide

67-68-5

dimethyl sulfoxide

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

A

112220-32-3

RuCl2(OS(CH3)2)(CH3C(CH2As(C6H5)2)3)

B

67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
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
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
ConditionsYield
In acetonitrile at 20℃; for 3h;A n/a
B 96%
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
ConditionsYield
at 50℃; for 5h; Elimination; acylation; retro-Pummerer reaction;A 3%
B 95%
C 67%
75-18-3

dimethylsulfide

A

67-71-0

dimethylsulfone

B

67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
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
ConditionsYield
In acetonitrile for 2h; Reflux;A 94%
B n/a
50450-21-0

dimethylbromosulphonium bromide

932-90-1

Benzaldoxime

A

67-68-5

dimethyl sulfoxide

B

100-47-0

benzonitrile

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

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
ConditionsYield
With ozone 1) CH2Cl2, -78 deg C, 2) Et2O, H2O;A 93%
B n/a
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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): IrritantXi
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.