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199885

Sigma-Aldrich

4(5)-Methylimidazole

98%

Synonym(s):

1H-4-Methylimidazole, 4(or 5)-Methylimidazole, 4-Methyl-1H-imidazole, 4-Methylimidazole, 5-Methyl-1H-imidazole, 5-Methylimidazole

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About This Item

Empirical Formula (Hill Notation):
C4H6N2
CAS Number:
822-36-6
Molecular Weight:
82.10
Beilstein:
1453
EC Number:
212-497-3
MDL number:
MFCD00005201
UNSPSC Code:
12352005
PubChem Substance ID:
24851942
NACRES:
NA.22

Quality Level

100

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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General description

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

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302 + H312,H314

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Cédric Moretton et al.
Journal of agricultural and food chemistry, 59(8), 3544-3550 (2011-03-09)
4-Methylimidazole (4MeI) is a nitrogen compound formed during the manufacture of class III and IV caramel colors. The European Commission has limited its content to 250 ppm. Two methods were compared to perform 4MeI quantification in caramels. The first one
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
Joon-Kwan Moon et al.
Journal of agricultural and food chemistry, 59(2), 615-618 (2010-12-29)
4(5)-Methylimidazole has received the attention of federal and state regulatory agencies because of its carcinogenicity and common presence in foods and beverages. In the present study, the formation of 4(5)-methylimidazole in Maillard reaction model systems consisting of D-glucose/NH(3), L-rhamnose/NH(3), methylglyoxal/NH(3)
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