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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/REAXYS Number:
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

signalword

Danger

Hazard Classifications

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

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 2

flash_point_f

314.6 °F - closed cup

flash_point_c

157 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD3882V
WXBD2731V
MKCK3992
MKBV5083V
MKBN5017V

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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
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
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
Young-Teck Kim et al.
Talanta, 78(3), 998-1003 (2009-03-10)
Based on the principle of liquid core waveguide, a novel microfluidic device with micro-scale detection window capable of sensing flashlight emitted from rapid 1,1'-oxalyldi-4-methylimidazole (OD4MI) chemiluminescence (CL) reaction was fabricated. Light emitted from OD4MI CL reaction occurring in the micro-dimensional
Kwang-Geun Lee et al.
Food chemistry, 136(3-4), 1165-1168 (2012-12-01)
Aqueous caramel model systems consisted the D-glucose/NH(3)/sulphite were heated at 100°C for 2 h and amounts of carcinogenic 4(5)-methylimidazole (4-MI) formed were determined. The amount formed ranged from 7.0 to 155.0 ppm. A system with 0.1 M sulphite yielded the
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