Dimethyl sulfoxide (DMSO) is a colorless liquid that has the ability to dissolve both polar and nonpolar compounds. It is commonly used as a solvent in organic reactions and as a cryoprotectant in cell preservation.
| IUPAC Name | Methylsulfinylmethane |
| Molecular Formula | C2H6OS |
| CAS Number | 67-68-5 |
| Synonyms | DMSO, Methyl sulfoxide, Dimethyl sulphoxide, Sulfinylbis(methane), Methane, sulfinylbis-, etc. |
| InChI | InChI=1S/C2H6OS/c1-4(2)3/h1-2H3 |
Dimethyl Sulfoxide Properties
Dimethyl Sulfoxide Formula
The chemical formula of DMSO is C2H6OS. It consists of two carbon atoms, six hydrogen atoms, and one sulfur atom, along with one oxygen atom. This colorless liquid compound is highly polar and can dissolve both polar and nonpolar compounds, making it a versatile solvent in many organic reactions.
Dimethyl Sulfoxide Molar Mass
The molar mass of DMSO is 78.13 g/mol. This value represents the mass of one mole of DMSO molecules. It is calculated by adding the atomic masses of all the constituent atoms in the molecule. The molar mass is an important parameter in many chemical calculations, including stoichiometry, solution concentration, and molecular weight determination.
Dimethyl Sulfoxide Boiling Point
The boiling point of DMSO is 189°C (372.2°F) at standard pressure. It has a relatively high boiling point due to the presence of strong dipole-dipole interactions between its molecules. This property makes it useful in various applications, such as in the production of polymers and pharmaceuticals.
Dimethyl Sulfoxide Melting Point
The melting point of DMSO is 18.5°C (65.3°F) at standard pressure. It is a low-melting-point compound, which allows it to remain liquid at room temperature. This property makes it a useful solvent in various applications, including in the preservation of cells and tissues.
Dimethyl Sulfoxide Density g/mL
The density of DMSO is 1.10 g/mL at standard temperature and pressure. It is a relatively dense liquid that is soluble in water and many other organic solvents. This property makes it an ideal solvent for a wide range of chemical reactions and processes.
Dimethyl Sulfoxide Molecular Weight
The molecular weight of DMSO is 78.13 g/mol. It is the sum of the atomic weights of all the atoms present in the molecule. The molecular weight is an important parameter in many chemical calculations, including determining the concentration of a solution and the weight of a substance.
Dimethyl Sulfoxide Structure
The structure of DMSO consists of a central sulfur atom attached to two methyl groups and one oxygen atom through covalent bonds. The sulfur atom has a lone pair of electrons, making the molecule highly polar. This structure allows it to dissolve both polar and nonpolar compounds, making it a versatile solvent in many organic reactions.
Dimethyl Sulfoxide Solubility
DMSO is a highly soluble compound in many organic solvents, including water, ethanol, acetone, and chloroform. Its high solubility allows it to dissolve a wide range of compounds, making it a useful solvent in various applications, such as in the production of pharmaceuticals and polymers.
| Appearance | Colorless liquid |
| Specific Gravity | 1.10 g/mL at 25°C |
| Color | Colorless |
| Odor | Odorless |
| Molar Mass | 78.13 g/mol |
| Density | 1.10 g/mL at 25°C |
| Melting Point | 18.5°C |
| Boiling Point | 189°C |
| Flash Point | 88°C |
| Water Solubility | Miscible |
| Solubility | Miscible in many organic solvents |
| Vapour Pressure | 0.003 mmHg at 25°C |
| Vapour Density | 2.7 (air=1) |
| pKa | 35 |
Dimethyl Sulfoxide Safety and Hazards
Dimethyl Sulfoxide (DMSO) is considered to be a relatively safe compound to handle and use. However, it should still be handled with care as it can cause irritation to the skin and eyes upon contact. Inhaling DMSO vapors may also cause irritation to the respiratory tract. It is important to wear appropriate personal protective equipment, such as gloves and goggles when handling DMSO. DMSO is flammable and should be kept away from open flames and sources of ignition. It is also important to store DMSO in a cool, dry, and well-ventilated area away from incompatible substances.
| Hazard Symbols | Xi |
| Safety Description | S24/25, S26, S36 |
| UN IDs | UN 1993 |
| HS Code | 2930.90.90 |
| Hazard Class | 3 |
| Packing Group | III |
| Toxicity | LD50 (oral, rat) = 14.5 g/kg |
Dimethyl Sulfoxide Synthesis Methods
A variety of methods can synthesize Dimethyl sulfoxide (DMSO).
One common method is the oxidation of dimethyl sulfide with oxygen or hydrogen peroxide in the presence of a catalyst, such as silver oxide or nitrogen dioxide.
Another method involves the reaction of dimethyl sulfide with sulfur trioxide followed by hydrolysis. One can synthesize DMSO by reacting dimethyl sulfate with sodium sulfite or sodium bisulfite.
A more recent method involves the direct synthesis of DMSO from dimethyl sulfide using an ionic liquid catalyst. This method has the advantage of being more environmentally friendly, as it does not require the use of harsh chemicals or high temperatures.
Regardless of the method used, the purity of the DMSO product is critical for its use in various applications. To obtain high-purity DMSO, people often employ purification steps such as distillation and crystallization. It is also important to handle DMSO with care during synthesis and purification, as it can be toxic and may pose a risk to human health and the environment if not properly handled.
Dimethyl Sulfoxide Uses
Dimethyl sulfoxide (DMSO) has a wide range of applications in various industries due to its unique properties. Here are some common uses of DMSO:
- Pharmaceutical Industry: Used as a solvent and as a transdermal penetration enhancer in drug formulations. Also used in cryopreservation of cells and tissues.
- Chemical Industry: Used as a solvent for various organic and inorganic compounds, as a reaction medium, and as a reducing agent in organic synthesis.
- Polymer Industry: Used as a solvent for the synthesis of various polymers, including polyurethanes and polyacrylonitrile.
- Biological Research: Used as a cryoprotectant for cells and tissues, as a reagent for protein crystallization, and as a solvent for membrane proteins.
- Veterinary Medicine: Used as a topical analgesic and anti-inflammatory agent for horses and dogs.
- Agriculture: Used as a fungicide and herbicide, as well as a growth regulator for plants.
- Electronics Industry: Used as a solvent and an electrolyte in the production of electronic devices.
- Paint and Coatings Industry: Also, used as a solvent and a dispersant in the production of paints and coatings.
Questions:
Q: Is dimethyl sulfoxide polar?
A: Yes, DMSO is a polar solvent due to its highly polar S=O bond and the presence of two polar methyl groups.
Q: Is dimethyl sulfoxide ionic or covalent?
A: DMSO is a covalent compound, as it consists of shared electrons between its atoms rather than the transfer of electrons between ions.
Q: What is dimethyl sulfoxide used for?
A: DMSO is commonly used as a solvent and a transdermal penetration enhancer in the pharmaceutical industry. It also has various applications in the chemical, polymer, biological research, agriculture, and electronics industries.
Q: Does dimethyl sulfoxide conduct electricity?
A: No, DMSO is a non-conductive solvent, meaning it does not conduct electricity.
Q: What is the mass % of carbon in dimethylsulfoxide (C2H6SO) rounded to three significant figures?
A: The molecular weight of C2H6SO is 78.13 g/mol. The mass of carbon in one mole of C2H6SO is 24.02 g/mol. Therefore, the mass % of carbon in dimethyl sulfoxide is 30.75%.
Q: What is the mass of carbon in dimethyl sulfoxide?
A: The molecular weight of DMSO is 78.13 g/mol. The mass of carbon in one mole of DMSO is 24.02 g/mol. Therefore, the mass of carbon in DMSO is 24.02 grams.
Q: Is DMSO solvent safe?
A: DMSO is generally safe when used appropriately, but it can cause skin irritation, allergic reactions, and other adverse effects if not handled properly. It is important to follow proper safety guidelines when handling DMSO.
Q: Which of the following alkyl halides reacts most slowly with NaN3 in dimethyl sulfoxide?
A: The reaction rate of an alkyl halide with NaN3 in DMSO depends on the nature of the alkyl group and the leaving group. Without knowing the specific alkyl halides in question, it is impossible to determine which one reacts most slowly.