Dimethyl fumarate (DMF) is a compound used in medicine to treat multiple sclerosis. It reduces inflammation and relapse rates by modulating the immune system.
IUPAC name | (E)-but-2-enedioic acid dimethyl ester |
Molecular formula | C6H8O4 |
CAS number | 624-49-7 |
Synonyms | DMF, Bioban, Fumaderm, Tecfidera, Dimethyl (E)-butenedioate |
InChI | InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+ |
Dimethyl Fumarate Properties
Dimethyl Fumarate Formula
The chemical formula of dimethyl fumarate is C6H8O4. It represents the specific arrangement and types of atoms present in the compound, consisting of 6 carbon (C) atoms, 8 hydrogen (H) atoms, and 4 oxygen (O) atoms. The formula provides a concise representation of dimethyl fumarate’s elemental composition.
Dimethyl Fumarate Molar Mass
The molar mass of DMF is calculated by summing the atomic masses of all its constituent elements. With a molecular formula of C6H8O4, the molar mass is found to be approximately 144.13 grams per mole. This value is crucial for various chemical calculations and conversions involving DMF.
Dimethyl Fumarate Boiling Point
DMF exhibits a boiling point of around 191 degrees Celsius (376 degrees Fahrenheit). The boiling point signifies the temperature at which the liquid compound changes into a gaseous state, and in the case of DMF, it occurs at this particular temperature.
Dimethyl Fumarate Melting Point
The melting point of DMF is approximately 102 degrees Celsius (216 degrees Fahrenheit). This temperature represents the point at which the solid form of the compound transitions into a liquid state. DMF undergoes this phase change at the specified melting point.
Dimethyl Fumarate Density g/mL
DMF possesses a density of about 1.30 grams per milliliter (g/mL). Density is a measure of how much mass is contained within a specific volume of a substance. In the case of DMF, it indicates the concentration of mass in each milliliter of the compound.
Dimethyl Fumarate Molecular Weight
The molecular weight of DMF, also known as its molar mass, is approximately 144.13 grams per mole. It is the sum of the atomic weights of all the atoms present in one molecule of DMF. The molecular weight is crucial for various chemical calculations and analyses.
Dimethyl Fumarate Structure
The structure of DMF consists of two methyl (CH3) groups attached to a central fumarate moiety. The fumarate moiety consists of two carboxylate groups connected by a double bond. This arrangement gives DMF its characteristic shape and chemical properties.
Dimethyl Fumarate Solubility
DMF is sparingly soluble in water but dissolves readily in organic solvents like ethanol or methanol. This limited solubility in water is a factor to consider when working with DMF and its applications in various industries.
Appearance | Colorless crystals or white powder |
Specific Gravity | 1.30 |
Color | Colorless |
Odor | Odorless |
Molar Mass | 144.13 g/mol |
Density | 1.30 g/mL |
Melting Point | 102 °C (216 °F) |
Boiling Point | 191 °C (376 °F) |
Flash Point | Not available |
Water Solubility | Sparingly soluble |
Solubility | Soluble in organic solvents (e.g., ethanol, methanol) |
Vapour Pressure | Not available |
Vapour Density | Not available |
pKa | Not available |
pH | Not available |
Dimethyl Fumarate Safety and Hazards
DMF should be handled with care to ensure safety. It may cause irritation if it comes into contact with the skin, eyes, or respiratory system. Adequate ventilation and protective equipment, such as gloves and goggles, are recommended during its use. Ingestion or inhalation of DMF should be avoided, as it may lead to health hazards. In case of accidental exposure, immediate medical attention is necessary. It is important to follow proper storage guidelines and keep the compound away from open flames or heat sources. Adhering to safety protocols minimizes the risks associated with DMF.
Hazard Symbols | None |
Safety Description | Avoid contact with skin, eyes, and respiratory system. Provide adequate ventilation. Wear protective equipment (gloves, goggles). Avoid ingestion and inhalation. Seek immediate medical attention in case of exposure. Store away from open flames or heat sources. |
UN IDs | Not applicable |
HS Code | 2917.19.90 |
Hazard Class | Not classified |
Packing Group | Not applicable |
Toxicity | May cause skin and eye irritation. Avoid ingestion and inhalation. |
Dimethyl Fumarate Synthesis Methods
There are various synthesis methods for DMF.
One common approach involves the esterification of fumaric acid using methanol. In this reaction, sulfuric acid or p-toluenesulfonic acid serves as an acid catalyst to combine fumaric acid with methanol. The reaction proceeds under reflux conditions, typically at an elevated temperature, to facilitate the esterification process. The acid catalyst actively promotes the reaction by facilitating the removal of water, which it causes as a byproduct.
Another method involves the reaction of maleic anhydride with methanol. Maleic anhydride and methanol react in the presence of an acid catalyst, such as sulfuric acid or phosphoric acid, to yield DMF. The reaction occurs through the opening of the cyclic anhydride ring and subsequent esterification.
To prepare DMF, one can perform a transesterification reaction using dimethyl maleate. In this process, dimethyl maleate reacts with methanol while a catalyst, such as sodium methoxide or potassium hydroxide, is present. The transesterification reaction leads to the formation of DMF.
These synthesis methods provide routes to obtain DMF in laboratory or industrial settings. Factors such as efficiency, yield, and availability of starting materials determine the choice of each method, as each method has its own advantages. Proper control of reaction conditions and purification steps are important to ensure the desired purity and quality of the synthesized DMF.
Dimethyl Fumarate Uses
DMF finds application in various fields due to its diverse properties. Here are some uses of DMF:
- Multiple Sclerosis Treatment: The FDA has approved DMF as a medication for treating relapsing forms of multiple sclerosis. It helps reduce relapse rates and inflammation by modulating the immune system.
- Pharmaceutical Industry: Pharmaceutical compounds utilize DMF as an intermediate in their synthesis. It serves as a building block for the production of various drugs.
- Antimicrobial Agent: DMF demonstrates antimicrobial properties. It finds application as a preservative in products like paints, coatings, and adhesives. It helps inhibit the growth of microorganisms and prevent spoilage.
- Textile Industry: The textile industry employs DMF as a powerful biocide for inhibiting the growth of mold and fungi on fabrics during storage and transportation.
- Furniture and Leather Goods: In the production of furniture, leather goods, and footwear, manufacturers use DMF as a mold and mildew inhibitor. It helps protect these items from microbial damage during storage and transit.
- Polymer Stabilizer: DMF acts as a stabilizer and antioxidant in polymers, such as polypropylene and polyethylene. It helps enhance their thermal stability and prolongs their shelf life.
- Chemical Reagent: Various chemical reactions, including esterifications and transesterifications, utilize DMF as a reagent. It facilitates the synthesis of esters and other organic compounds.
These are just a few examples of the diverse applications of DMF across industries. Its unique properties make it a valuable compound in the fields of medicine, manufacturing, preservation, and chemistry.
Questions:
Q: How to remove dimethyl fumarate from furniture?
A: DMF can be removed from furniture by wiping the affected areas with a mild soap solution or using a cleaning agent specifically designed to remove stains and residues.
Q: Which is more polar, diethyl maleate or dimethyl fumarate?
A: DMF is more polar than diethyl maleate due to the presence of the electron-withdrawing carbonyl groups in its structure.
Q: What is dimethyl fumarate used for?
A: DMF is used in the treatment of multiple sclerosis and also finds applications in the pharmaceutical industry, as a preservative, and in the textile and polymer industries.
Q: What two functional groups are in dimethyl maleate and dimethyl fumarate?
A: Dimethyl maleate and DMF both contain ester and alkene functional groups.
Q: Can you be allergic to smelling dimethyl fumarate?
A: Yes, some individuals may develop allergic reactions upon smelling DMF, resulting in symptoms such as skin irritation, respiratory problems, or allergic dermatitis.
Q: Is dimethyl maleate and dimethyl fumarate reversible?
A: No, dimethyl maleate and DMF are not reversible. They are different isomers of the same compound and do not readily interconvert.
Q: What laboratory technique will you use to purify the reaction product dimethyl fumarate?
A: Distillation is commonly used to purify the reaction product DMF by separating it from impurities based on differences in boiling points.