1-METHYLIMIDAZOLE

1-Methylimidazole is a chemical compound belonging to the imidazole family, characterized by a five-membered ring structure containing two nitrogen atoms. 
It is a colorless to pale yellow liquid with a distinctive odor. 
The compound is used as a base in various industrial applications, particularly in the synthesis of pharmaceuticals, agrochemicals, and resins. 
It also plays a role in the preparation of catalysts and has applications in the synthesis of ionic liquids.

CAS Number: 616-47-7
Synonyms:,1-Methyl-1H-imidazole,1-Methylimidazole,1-Methylimidazoline,Methylimidazole

Introduction
Overview of Methylimidazole:
Methylimidazole is an organic compound with the formula C₄H₆N₂. 
It consists of an imidazole ring (a five-membered ring with two nitrogen atoms) substituted with a methyl group (-CH₃) at one of the carbon positions. 
This compound plays a significant role in the synthesis of pharmaceuticals, agrochemicals, and materials science. 
It exists in multiple isomeric forms, including 2-methylimidazole and 4-methylimidazole, which have distinct properties and applications.

Chemical Structure and Classification:
The imidazole ring is a heterocyclic aromatic structure, containing nitrogen atoms that make it highly reactive. 
Methylimidazole is classified under heterocycles and is often used as a building block in organic synthesis due to its nitrogen-containing ring, which can coordinate with metals or participate in various chemical reactions.
It also has potential applications in medicinal chemistry due to its interaction with enzymes and receptors.

Historical Development and Discovery:
Methylimidazole was first synthesized in the early 20th century. 
Its significance in chemical and biological processes was realized over time, especially after its discovery as a by-product of certain amino acid metabolism. 
Since then, the compound has found uses in a variety of fields, particularly in drug discovery and chemical manufacturing.

Chemical Properties
Molecular Formula and Weight:
Methylimidazole has the molecular formula C₄H₆N₂, with a molecular weight of approximately 82.1 g/mol.
This compact structure gives it a relatively low molecular weight compared to larger organic compounds.

Chemical Structure and Isomerism:
The structure of Methylimidazole consists of a five-membered ring with two nitrogen atoms located at positions 1 and 3 (or 1 and 4, depending on the isomer). 
The methyl group (-CH₃) is attached to one of the carbons. 
The isomeric forms (2-methylimidazole and 4-methylimidazole) differ based on the position of the methyl group, with different physical and chemical properties.

Physical Properties:
Boiling Point: Approximately 167-170°C
Melting Point: 90-92°C
Solubility: Highly soluble in water and many organic solvents like ethanol and acetone.
Density: Typically ranges from 1.1 to 1.2 g/cm³
Reactivity: Methylimidazole is reactive due to its nitrogen atoms and can undergo nucleophilic substitution reactions, coordination with metals, and hydrogen bonding.

Reactivity and Stability:
Methylimidazole can react with electrophiles, such as alkylating agents, or participate in condensation reactions. 
In certain conditions, it can also form salts with acids, which are highly soluble in water.

Synthesis and Production Methods
Methods for Synthesizing Methylimidazole:
Methylimidazole can be synthesized through several methods:
Cyclization of α-haloamines: This is one of the most common methods, where a suitable α-haloamine undergoes cyclization to form the imidazole ring.

Methylation of imidazole: Imidazole can be methylated using methylating agents such as methyl iodide (CH₃I) in the presence of a base, yielding methylimidazole.

Direct alkylation of imidazole: A method involving the direct methylation of imidazole using methylating reagents like dimethyl sulfate or methyl chloride.

Industrial Production Processes:
On an industrial scale, methylimidazole is often synthesized by a one-pot reaction, starting with precursors like imidazole and methylating agents. 
This reaction can take place under controlled conditions of temperature and solvent choice to maximize yield and purity.

Raw Materials and Catalysts Used:
Common raw materials for the synthesis of methylimidazole include imidazole, methylating agents (such as methyl iodide or dimethyl sulfate), and solvents like dimethylformamide (DMF) or acetone. Catalysts may include base catalysts (such as sodium hydroxide) or acidic catalysts, depending on the method of synthesis.

4. Applications
Pharmaceuticals:
Methylimidazole is a crucial component in the synthesis of several biologically active compounds, including antifungal agents. 
The compound itself, and its derivatives, are involved in drug formulations due to their bioactivity and ability to interact with biological targets.

Chemical Synthesis:
Methylimidazole is widely used as a catalyst in chemical reactions, particularly in the production of pharmaceuticals and agrochemicals. 
It also serves as a reagent in the synthesis of heterocyclic compounds.

Polymer Industry:
Methylimidazole is used in the production of resins, particularly those that require a nitrogen-rich heterocyclic structure for enhanced stability or functionality. 
It is also used in the development of new polymer materials, especially in electronics and coatings.

Other Industrial and Commercial Uses:
Methylimidazole is used as an intermediate in the synthesis of agricultural chemicals, such as fungicides and herbicides. 
It also plays a role in the production of corrosion inhibitors and other specialty chemicals.

SAFETY INFORMATION ABOUT 1-METHYLIMIDAZOLE

 
 
First aid measures:
Description of first aid measures:
General advice:
Consult a physician. 
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
 
If inhaled:
If breathed in, move person into fresh air. 
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately. 
Wash off with soap and plenty of water.
Consult a physician.
 
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
 
If swallowed:
Do NOT induce vomiting. 
Never give anything by mouth to an unconscious person. 
Rinse mouth with water. 
Consult a physician.
 
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
 
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. 
 
Avoid breathing vapours, mist or gas. 
Evacuate personnel to safe areas.
 
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste. 
Keep in suitable, closed containers for disposal.
 
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
 
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place. 
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
 
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
 
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles. 
Faceshield (8-inch minimum). 
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
 
Skin protection:
Handle with gloves. 
Gloves must be inspected prior to use. 
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product. 
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. 
Wash and dry hands.
 
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
 
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. 
 
If the respirator is the sole means of protection, use a full-face supplied air respirator. 
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. 
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions. 
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
 
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company. 
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product