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616-47-7 - 1-Methylimidazole, 99% - A12575 - Alfa Aesar

A12575 1-Methylimidazole, 99%

CAS Number
616-47-7
Synonyms

Size Price ($) Quantity Availability
100g 27.19
500g 96.90
2kg 264.71
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1-Methylimidazole, 99%

MDL
MFCD00005292
EINECS
210-484-7

Chemical Properties

Formula
C4H6N2
Formula Weight
82.11
Melting point
-6°
Boiling Point
195-197°
Flash Point
92°(197°F)
Density
1.031
Refractive Index
1.4970
Sensitivity
Hygroscopic
Solubility
Miscible with water.

Applications

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.

Notes

Incompatible with carbon dioxide and strong oxidizing agents.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H302-H312-H227

Causes severe skin burns and eye damage. Harmful if swallowed. Harmful in contact with skin. Combustible liquid.

Precautionary Statements: P210-P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. 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 IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
105197
Hazard Class
8
Packing Group
III
Harmonized Tariff Code
2933.29
TSCA
Yes
RTECS
NI7000000

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