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

A12575 1-Methylimidazole, 99%

Codice CAS
616-47-7
Sinonimi

Dimensioni Prezzo ($) Quantità Disponibilità
100g 27,60
500g 105,00
2kg 269,00
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1-Methylimidazole, 99%

MDL
MFCD00005292
EINECS
210-484-7

Proprietà chimiche

Formula
C4H6N2
Peso formula
82.11
Punto di fusione
-6°
Punto di ebollizione
195-197°
Punto di infiammabilità
92°(197°F)
Densità
1.031
Indice di rifrazione
1.4970
Sensibilità
Hygroscopic
Solubilità
Miscible with water.

Applicazioni

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.

Note

Incompatible with carbon dioxide and strong oxidizing agents.

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H227-H302-H312-H314

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

Dichiarazioni precauzionali: P210u-P260u-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dusts or mists. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
105197
Classe di rischio
8
Gruppo di imballaggio
III
Codice tariffe armonizzato
2933.29
TSCA
Yes
RTECS
NI7000000

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