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1-Methylimidazole is used as a precursor for the synthesis of pyrrole-imidazole polyamides, ionic liquids such as 1-butyl-3-methylimidazolium hexafluorophosphate. It is actively involved in removing acid during the production of diethoxyphenylphosphine. It is used as an intermediate in organic synthesis.
Useful base for peptide coupling, etc. See, e.g.: J. Chem. Soc., Chem. Commun., 2223 (1995). For peptide reagents, see Appendix 6.
Undergoes lithiation at the 2-position. Reaction of the Li derivative with ketones followed by dehydration with acetic anhydride is a good route to 2-alkylideneimidazoles: Synthesis, 78 (1990). Likewise, reaction with benzonitrile gives the 2-benzoyl derivative, the carbonyl group of which undergoes Wittig methylenation: Synth. Commun., 20, 321 (1990).
Reacts with acid chlorides, including chloroformates, to give N-acylimidazolium salts, which are useful reagents for the acylation of, for example, amino acids: Bull. Soc. Chim. Fr., 1021 (1973).
Zhang, Y.; Yin, S. C.; Lu, J. M. N-Heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed allyl-aryl coupling of allylic alcohols with arylboronic acids in neat water. Tetrahedron 2015, 71 (4), 544-549.
Guan, J. T.; Song, X. M.; Zhang, Z. Y.; Wei, B. M.; Dai, Z. Q. Catalytic activity of 1-methylimidazole-based phosphine ligands in the palladium-catalyzed Suzuki coupling reaction. Appl. Organomet. Chem. 2015, 29 (2), 87-89.
Hazard Statements: H227-H302-H311-H314-H335
Combustible liquid. Harmful if swallowed. Toxic in contact with skin. Causes severe skin burns and eye damage. May cause respiratory irritation.
Precautionary Statements: P210-P235-P260-P264b-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep cool. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant