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199885

Sigma-Aldrich

4(5)-Methylimidazole

98%

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Synonym(s):
1H-4-Methylimidazole, 4(or 5)-Methylimidazole, 4-Methyl-1H-imidazole, 4-Methylimidazole, 5-Methyl-1H-imidazole, 5-Methylimidazole
Empirical Formula (Hill Notation):
C4H6N2
CAS Number:
Molecular Weight:
82.10
Beilstein:
1453
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

bp

263 °C (lit.)

mp

44-47 °C (lit.)

solubility

H2O: soluble, clear, colorless to yellow (50 mg/mL)

SMILES string

Cc1c[nH]cn1

InChI

1S/C4H6N2/c1-4-2-5-3-6-4/h2-3H,1H3,(H,5,6)

InChI key

XLSZMDLNRCVEIJ-UHFFFAOYSA-N

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1 of 4

This Item
336092239348M50834
4(5)-Methylimidazole 98%

199885

4(5)-Methylimidazole

1-Methylimidazole ≥99%, purified by redistillation

336092

1-Methylimidazole

2-Ethylimidazole 98%

239348

2-Ethylimidazole

1-Methylimidazole ReagentPlus®, 99%

M50834

1-Methylimidazole

Quality Level

100

Quality Level

300

Quality Level

200

Quality Level

-

solubility

H2O: soluble, clear, colorless to yellow (50 mg/mL)

solubility

-

solubility

-

solubility

water: soluble

mp

44-47 °C (lit.)

mp

−6 °C (lit.)

mp

78-81 °C (lit.)

mp

−6 °C (lit.)

bp

263 °C (lit.)

bp

198 °C (lit.)

bp

268 °C (lit.)

bp

198 °C (lit.)

General description

4(5)-Methylimidazole was quantified in coffee by GC-MS method.

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Skin Corr. 1B

Storage Class Code

8A - Combustible, corrosive hazardous materials

WGK

WGK 2

Flash Point(F)

314.6 °F - closed cup

Flash Point(C)

157 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Satoshi Ueda et al.
Journal of the American Chemical Society, 134(1), 700-706 (2011-12-01)
The completely N(1)-selective Pd-catalyzed arylation of unsymmetric imidazoles with aryl halides and triflates is described. This study showed that imidazoles have a strong inhibitory effect on the in situ formation of the catalytically active Pd(0)-ligand complex. The efficacy of the
Ileana Elder et al.
Archives of biochemistry and biophysics, 437(1), 106-114 (2005-04-12)
In the site-specific mutant of human carbonic anhydrase in which the proton shuttle His64 is replaced with alanine, H64A HCA II, catalysis can be activated in a saturable manner by the proton donor 4-methylimidazole (4-MI). From 1H NMR relaxivities, we
S Casal et al.
Journal of chromatography. A, 976(1-2), 285-291 (2002-12-05)
A GC-MS method is described for quantification of 4-(5-)methylimidazole (4MI) in coffee. Although tested, GC-flame ionization detection proved inadequate for this purpose due to the complexity of the coffee matrix. The developed method was based on ion-pair extraction with bis-2-ethylhexylphosphate
Hitomi Yamaguchi et al.
Journal of agricultural and food chemistry, 59(18), 9770-9775 (2011-09-02)
A method for the determination of 4(5)-methylimidazole (4MeI) in naturally brewed soy sauce was developed for the first time using solid-phase extraction (SPE) and liquid chromatography-tandem mass spectrometry (LC-MS/MS). SPE on silica-based reversed-phase cartridges with heptafluorobutyric acid as an ion-pairing
Matt Hengel et al.
Journal of agricultural and food chemistry, 61(4), 780-789 (2013-01-09)
Since the National Toxicology Program (NTP) identified 4(5)-methylimidazole [4(5)-MI] as a cancer causing chemical in 2007 and the State of California added it to the Proposition 65 list of compounds as a carcinogen on January 7, 2011, many researchers and

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