Summary of 1-Methylimidazole

Product Name: 1-Methylimidazole
Molecular Formula: C4H6N2
Molecular Weight: 82.1
EINECS: 210-484-7
CAS Data Base Reference: 616-47-7
Chemical Properties: 1-Methylimidazole is clear colorless to yellow liquid.
Usage: A metabolite of 1-methyl-2-thioimidazole. It inhibits bone resorption.
Stability: Stable, but moisture sensitive. Incompatible with acids, acid anhydrides, strong oxidizing agents, moisture, carbon dioxide, acid chlorides.

1-Methylimidazole(CAS NO:616-47-7) is an aromatic heterocyclic organic compound with the formula CH3C3H3N2. It is a colourless liquid that is used as a specialty solvent, a base, and as a precursor to some ionic liquids. It is fundamental nitrogen heterocycle and as such mimics for various nucleoside bases as well as histidine and histamine.

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.

1-Methylimidazole 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

The compound 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 + NaOH → H2C2N(NCH3)CH + H2O + NaI

In the research laboratory, 1-methylimidazole and related derivatives have been used as mimic aspects of diverse imidazole-based biomolecules. It 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 1-methylimidazole as a means to remove acid during their industrial-scale production of diethoxyphenylphosphine. In this biphasic acid scavenging using ionic liquids (BASIL) process, 1-methylimidazole reacts with HCl to produce 1-methylimidazolium chloride, a salt that is easily separated and deprotonated to regenerate 1-methylimidazole.


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