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N-Methylimidazole (NMI) is an important raw material for the synthesis of pharmaceutical intermediates, used in the preparation of losartan, nizofenone, 1-Methyl-1H-imidazole-5-carbonyl chloride hydrochloride and naphazoline hydrochloride, etc.
N-Methylimidazole (NMI) is also used as a specialty solvent, a base, and as a precursor to some ionic liquids.
N-Methylimidazole (NMI) is an aromatic heterocyclic organic compound with the formula CH3C3H3N2.
CAS Number: 616-47-7
Molecular Formula: C4H6N2
Molecular Weight: 82.1
EINECS Number: 210-484-7
Synonyms: 1-methylimidazole, 1-Methyl-1H-imidazole, 616-47-7, 1H-Imidazole, 1-methyl-, IMIDAZOLE, 1-METHYL-, N1-Methylimidazole, Araldite DY 070, EINECS 210-484-7, UNII-P4617QS63Y, NSC 88064, DTXSID6052291, CHEBI:113454, P4617QS63Y, NSC-88064, 1-methyl-1H-imidazol-3-ium, DTXCID6030863, EC 210-484-7, THIAMAZOLE IMPURITY B [EP IMPURITY], THIAMAZOLE IMPURITY B (EP IMPURITY), 1-methylimidazolium ethanoate, NMethylimidazole, Imidazole, 1methyl, 1HImidazole, 1methyl, 210-484-7, inchi=1/c4h6n2/c1-6-3-2-5-4-6/h2-4h,1h, mctwtzjpvlrjou-uhfffaoysa-n, un2922, N-Methylimidazole, N-methylimidazol, 1-methylimidazol, n-methyl imidazole, MFCD00005292, 1-methyl-imidazole, 1-methylimdazole, 1-Methyl-1H-imidazole; Thiamazole Imp. B (EP); Thiamazole Impurity B, 3-methylimidazole, N-methyl-imidazol, N-methyl-imidazole, 1-methyl imidazole, 1-N-methylImidazole, Lopac-M-8878, 1-methyl-(1H)-imidazole, CHEMBL543, 1-Methyl-1H-imidazole #, WLN: T5N CNJ A1, Lopac0_000831, 3-methyl-1H-imidazol-3-ium, BDBM7884, HMS3262H03, BCP29437, NSC88064, STR00990, Tox21_304006, Tox21_500831, BBL011447, STL146559, AKOS000119840, CCG-204915, CS-W008580, FM00853, LP00831, PS-9372, SDCCGSBI-0050808.P002, NCGC00015702-01, NCGC00015702-02, NCGC00015702-03, NCGC00015702-04, NCGC00094162-01, NCGC00094162-02, NCGC00261516-01, NCGC00357222-01, 1-Methylimidazole, ReagentPlus(R), 99%, 1-Methylimidazole, redistilled from glass, CAS-616-47-7, FM179985, PD015169, DB-002020, EU-0100831, M0508, NS00009025, EN300-21628, 1-Methylimidazole, puriss., >=99.0% (GC), D70869, M 8878, 1-Methylimidazole, Vetec(TM) reagent grade, 98%, SR-01000076013, Q4545792, SR-01000076013-1, 1-Methylimidazole, >=99%, purified by redistillation, F0001-1635, Z104506032, 1-Methyl-1H-imidazole;N-Methylimidazole;1H-Imidazole, 1-methyl-, Cap B (1-methylimidazole 16% in THF), for oligonucleotide synthesis, filtered through a 1mum filter, Capping B (10 % N-methylimidazole in THF / pyridine, V / V = 80 : 10) NC-0803 emp Biotech GmbH, Capping B, 16 % NMI in THF, emp Biotech GmbH (THF/N-methylimidazole, V / V = 84 : 16) NC-0801, 450ml : 28-400 thread, 2.5L : GL45 thread, N-methylimidazole (1-methylimidazole);N-methyl midazole;N-methyl glyoxaline;CAP B (1-METHYLIMIDAZOLE 12% IN ACETONIT;1-Methylimidazole, >=99%, purified by redistillation;CAP B (1-METHYLIMIDAZOLE 10% IN THF)*;CAP B (1-METHYLIMIDAZOLE 10% IN;CAP B (1-METHYLIMIDAZOLE 16% IN THF)*
N-Methylimidazole (NMI) is an aromatic heterocyclic organic compound with the formula CH3C3H3N2.
N-Methylimidazole (NMI) is a colorless to yellow liquid, with an amine-like odor.
N-Methylimidazole (NMI) is miscible with water.
N-Methylimidazole (NMI) is a colourless liquid that is used as a specialty solvent, a base, and as a precursor to some ionic liquids.
It is a fundamental nitrogen heterocycle and as such mimics for various nucleoside bases as well as histidine and histamine.
N-Methylimidazole (NMI) is an organic compound that belongs to the imidazole family, characterized by a five-membered ring containing two nitrogen atoms.
Specifically, N-Methylimidazole (NMI) is a methylated derivative of imidazole, where a methyl group (-CH₃) is attached to one of the nitrogen atoms in the ring structure.
This structural modification significantly alters the compound's chemical behavior, making it more basic and more nucleophilic compared to imidazole itself.
N-Methylimidazole (NMI) appears as a clear, colorless to yellow liquid, and it is known for being both hygroscopic (readily absorbing moisture from the air) and soluble in water and organic solvents such as methanol and chloroform.
N-Methylimidazole (NMI) has a relatively high boiling point and a low vapor pressure, which makes it stable under standard laboratory conditions, although it is sensitive to acids and moisture.
N-Methylimidazole (NMI) is a 1H-imidazole having a methyl substituent at the N-1 position.
It is a metabolite of 1-methyl-2-thioimidazole (methimazole).
N-Methylimidazole (NMI) inhibits bone resorption.
With the N-methyl group, this particular derivative of imidazole cannot tautomerize.
It is slightly more basic than imidazole, as indicated by the pKa's of the conjugate acids of 7.0 and 7.4.
Methylation also provides a significantly lower melting point, which makes 1-methylimidazole a useful solvent.
N-Methylimidazole (NMI) must be handled with care due to its hazardous properties.
It can be irritating to the skin, eyes, and respiratory tract upon exposure, and it may cause serious health effects if inhaled or ingested in significant amounts.
Proper protective measures such as gloves, goggles, and adequate ventilation should always be employed when working with this chemical.
N-Methylimidazole (NMI) is prepared mainly by two routes industrially. The main one is acid-catalysed methylation of imidazole by methanol.
The second method involves the Radziszewski reaction from glyoxal, formaldehyde, and a mixture of ammonia and methylamine.
(CHO)2 + CH2O + CH3NH2 + NH3 → H2C2N(NCH3)CH + 3 H2O
N-Methylimidazole (NMI) can be synthesized on a laboratory scale by methylation of imidazole at the pyridine-like nitrogen and subsequent deprotonation.
Similarly, 1-methylimidazole may be synthesized by first deprotonating imidazole to form a sodium salt followed by methylation: H2C2N(NH)CH + CH3I → [H2C2(NH)(NCH3)CH]I, [H2C2(NH)(NCH3)CH]I + NaOH → H2C2N(NCH3)CH + H2O + NaI
N-Methylimidazole (NMI) is a derivative of imidazole, a five-membered heterocyclic ring that contains two nitrogen atoms.
N-Methylimidazole (NMI) has a methyl group attached to one of the nitrogen atoms in the imidazole ring.
N-Methylimidazole (NMI) acts as a strong base and is often used as a catalyst or intermediate in organic synthesis.
Its nitrogen atoms can readily participate in hydrogen bonding and electron pair donation, which is useful in forming coordination complexes and activating electrophilic centers in reactions.
N-Methylimidazole (NMI) is widely used in both academic and industrial chemical processes, especially in the synthesis of pharmaceuticals, agrochemicals, and polymer materials.
Melting point, −60 °C (lit.)
Boiling point, 198 °C (lit.)
Density, 1.03 g/mL at 25 °C (lit.)
Vapor pressure, 0.4 mm Hg (20 °C)
Refractive index, n20/D 1.495 (lit.)
Flash point, 198 °F
Storage temp., Store below +30 °C
Solubility, Chloroform (Slightly), Methanol (Slightly)
Form, Liquid
pKa, 6.95 (at 25 °C)
Specific gravity, 1.031
Color, Clear colorless to yellow
pH, 9.5–10.5 (50 g/L, H₂O, 20 °C)
pH range, 9.5–11.5 at 100 g/L at 20 °C
Biological source, Synthetic
Explosive limit, 2.7–15.7% (V)
Water solubility, Miscible with water
Sensitive, Hygroscopic
BRN, 105197
Stability, Stable, but moisture sensitive. Incompatible with acids, acid anhydrides, strong oxidizing agents, moisture, carbon dioxide, acid chlorides.
InChIKey, MCTWTZJPVLRJOU-UHFFFAOYSA-N
LogP, -0.19 at 25 °C
N-Methylimidazole (NMI) is an important heterocyclic organic compound widely used in various fields of chemistry due to its unique structural and chemical properties.
Structurally, N-Methylimidazole (NMI) consists of an imidazole ring, a five-membered ring containing two nitrogen atoms at non-adjacent positions, with one of the nitrogen atoms substituted by a methyl group.
This methyl substitution enhances the electron density on the nitrogen atom, making N-Methylimidazole (NMI) significantly more nucleophilic and basic than its parent compound, imidazole.
Because of its enhanced basicity and nucleophilicity, N-Methylimidazole (NMI) serves as an efficient catalyst and reagent in many chemical reactions, particularly those involving acylation, alkylation, and polymerization processes.
N-Methylimidazole (NMI) can accelerate reactions by acting as a proton acceptor or by stabilizing intermediates, which leads to improved reaction rates and yields.
Its ability to form stable hydrogen bonds and coordinate with metal ions also makes it valuable in the synthesis of complex organometallic compounds and pharmaceutical intermediates.
N-Methylimidazole (NMI) is typically encountered as a clear, colorless to pale yellow liquid that is hygroscopic, meaning it readily absorbs moisture from the environment.
It has a relatively high boiling point of around 198 °C, which allows it to be used in high-temperature reactions without significant evaporation.
N-Methylimidazole (NMI) is miscible with many organic solvents as well as water, which provides versatility for use in different solvent systems.
N-Methylimidazole (NMI) is a derivative of imidazole that is utilized in the manufacture of such classes of items as pharmaceuticals, pesticides, ion-exchange resins, dye intermediates, textile auxiliaries, photographic chemicals, and corrosion inhibitors.
It is also used as a catalyst for manufacturing polyurethanes and a curing agent for epoxy resins.
N-Methylimidazole (NMI) is commonly used as a curing agent or accelerator in epoxy resin formulations, improving the mechanical properties and chemical resistance of the resulting polymers.
It also plays a critical role in the pharmaceutical industry where it is employed as a building block or catalyst in the manufacture of active pharmaceutical ingredients (APIs), helping to produce medications more efficiently and cost-effectively.
N-Methylimidazole (NMI) to form dialkyl imidazolium salts. Depending on the alkylating agent and the counteranion, various ionic liquids result, e.g. 1-butyl-3-methylimidazolium hexafluorophosphate.
N-Methylimidazole (NMI)’s combination of chemical reactivity, physical stability, and versatility makes it an indispensable reagent in both research laboratories and commercial chemical manufacturing processes.
Preparation:
N-Methylimidazole (NMI) is prepared mainly by two routes industrially.
The main one is acid-catalysed methylation of imidazole by methanol.
The second method involves the Radziszewski reaction from glyoxal, formaldehyde, and a mixture of ammonia and methylamine.
(CHO)2 + CH2O + CH3NH2 + NH3 → H2C2N(NCH3)CH + 3 H2O
N-Methylimidazole (NMI) can be synthesized on a laboratory scale by methylation of imidazole at the pyridine-like nitrogen and subsequent deprotonation.
Similarly, 1-methylimidazole may be synthesized by first deprotonating imidazole to form a sodium salt followed by methylation. H2C2N(NH)CH + CH3I → [H2C2(NH)(NCH3)CH]I, [H2C2(NH)(NCH3)CH]I + NaOH → H2C2N(NCH3)CH + H2O + NaI
Uses:
N-Methylimidazole (NMI) is an aprotic solvent.
It is a derivative of imidazole used in the production of pharmaceuticals, pesticides, ion exchange resins, dye intermediates, textile auxiliaries, photographic chemicals, and corrosion inhibitors.
It can also be used as a catalyst for the manufacture of polyurethane and a curing agent for epoxy resins.
For example, when N-Methylimidazole (NMI) is added to an aqueous diethylenetriamine (DETA) solution, high CO2 loading can be achieved through phase separation of the absorbent during CO2 absorption.
In the research laboratory, N-Methylimidazole (NMI) and related derivatives have been used as mimic aspects of diverse imidazole-based biomolecules.
N-Methylimidazole (NMI) is also the precursor for the synthesis of the methylimidazole monomer of pyrrole-imidazole polyamides.
These polymers can selectively bind specific sequences of double-stranded DNA by intercalating in a sequence dependent manner.
BASF has used N-Methylimidazole (NMI) as a means to remove acid during their industrial-scale production of diethoxyphenylphosphine.
In this biphasic acid scavenging using ionic liquids (BASIL) process, N-Methylimidazole (NMI) reacts with HCl to produce 1-methylimidazolium hydrochloride, which spontaneously separates as a separate liquid phase under the reaction conditions.
N-Methylimidazole (NMI) is used as a solvent in various chemical reactions, including pharmaceuticals, polymers, and dyes.
It is also used as a catalyst in the production of biofuels.
N-Methylimidazole (NMI) is used as a proton source in electrochemical applications, such as fuel cells and electroplating.
N-Methylimidazole (NMI) is used as a base in the synthesis of various drugs, including antifungal agents, antiviral drugs, and antibiotics.
It is also used in the production of active pharmaceutical ingredients.
N-Methylimidazole (NMI) is used as a flavoring agent and preservative in the food industry.
N-Methylimidazole (NMI) is added to various food products, including baked goods, meats, and beverages.
N-Methylimidazole (NMI) is used as a chain transfer agent in the production of various polymers, including polyethylene and polypropylene.
N-Methylimidazole (NMI) is used as a reagent in biological research, including the synthesis of peptides and nucleic acids.
N-Methylimidazole (NMI) finds application in the agrochemical industry, where it serves as a building block or catalyst in the production of herbicides and pesticides, contributing to the creation of compounds that protect crops more effectively.
It is also used in polymer chemistry beyond epoxy resins, including the synthesis of polyurethanes and other specialty polymers, where it facilitates polymerization reactions and enhances the final material properties.
Due to its ability to coordinate with metal ions, N-Methylimidazole is frequently employed in the development of coordination complexes and catalysts in organometallic chemistry, where it can influence the selectivity and efficiency of catalytic cycles.
This makes it a valuable reagent for research and industrial processes aiming to produce fine chemicals and specialty materials.
In summary, the diverse chemical reactivity and physical properties of N-Methylimidazole (NMI) make it indispensable across a wide range of industries, including pharmaceuticals, polymers, agrochemicals, and catalysis, where it significantly contributes to the efficiency, quality, and performance of numerous chemical products and processes.
N-Methylimidazole (NMI) is extensively utilized in the chemical industry as a highly effective catalyst, particularly in reactions that require the activation of acyl groups, such as esterifications and amidations, where its strong basicity helps accelerate the formation of target molecules by facilitating proton transfer and stabilizing reactive intermediates.
N-Methylimidazole (NMI) is also commonly employed as a curing agent in the production of epoxy resins, where it acts to speed up the cross-linking process, improving the mechanical strength, chemical resistance, and thermal stability of the final polymer products, making them suitable for use in coatings, adhesives, and composite materials.
In pharmaceutical manufacturing, N-Methylimidazole (NMI) plays a crucial role as an intermediate or catalyst in the synthesis of various active pharmaceutical ingredients (APIs). Its ability to participate in nucleophilic substitution and condensation reactions allows chemists to efficiently build complex molecular structures necessary for drug development.
Additionally, N-Methylimidazole (NMI) is valued for its use in the preparation of ionic liquids and as a stabilizer in chromatographic techniques, where it helps maintain the pH and ionic environment, thereby improving the resolution and reproducibility of analytical separations.
Safety Profile:
N-Methylimidazole (NMI) poses several health hazards primarily due to its chemical nature as a reactive, basic heterocyclic amine.
It can cause severe irritation to the skin, eyes, and respiratory tract upon contact or inhalation, leading to redness, pain, and potential damage to mucous membranes.
Prolonged or repeated exposure may result in dermatitis or more serious skin conditions, as N-Methylimidazole (NMI) can penetrate the skin and cause systemic toxicity.
Inhalation of vapors or aerosols may provoke coughing, shortness of breath, and in severe cases, chemical pneumonitis, highlighting the need for adequate ventilation and respiratory protection when handling the substance.
From a toxicological standpoint, N-Methylimidazole (NMI) exhibits moderate acute toxicity if ingested, inhaled, or absorbed through the skin, with symptoms including nausea, dizziness, headache, and in extreme cases, central nervous system effects such as confusion or loss of consciousness.
N-Methylimidazole (NMI) is also suspected of having mutagenic properties based on animal studies, which raises concerns about potential long-term health effects such as genetic damage or carcinogenicity, though conclusive evidence in humans is limited.
Due to these risks, careful handling and strict adherence to safety protocols are essential in both laboratory and industrial environments.
