199885

4(5)-Methylimidazole

Name: 4(5)-Methylimidazole
Brand: ALDRICH

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

UNSPSC Code:

12352005

NACRES:

NA.22

PubChem Substance ID:

24851942

EC Number:

212-497-3

Beilstein/REAXYS Number:

1453

MDL number:

MFCD00005201

Key Documents

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Product Name

4(5)-Methylimidazole, 98%

assay

98%

InChI key

XLSZMDLNRCVEIJ-UHFFFAOYSA-N

InChI

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

SMILES string

Cc1c[nH]cn1

bp

263 °C (lit.)

mp

44-47 °C (lit.)

solubility

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

Quality Level

100

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Show Differences

1 of 4

This Item	190675	284424	239348
Sigma-Aldrich 199885 4(5)-Methylimidazole	Sigma-Aldrich 190675 4-Methyl-5-thiazoleethanol	Sigma-Aldrich 284424 4-Allyl-1,2-dimethoxybenzene	Sigma-Aldrich 239348 2-Ethylimidazole
assay 98%	assay 98%	assay 99%	assay 98%
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 200
solubility H₂O: soluble, clear, colorless to yellow (50 mg/mL)	solubility alcohol: soluble(lit.), benzene: soluble(lit.), chloroform: soluble(lit.), diethyl ether/hexanes: soluble(lit.), water: very soluble(lit.)	solubility -	solubility -
bp 263 °C (lit.)	bp 135 °C/7 mmHg (lit.)	bp 254-255 °C (lit.)	bp 268 °C (lit.)
mp 44-47 °C (lit.)	mp -	mp −4 °C (lit.)	mp 78-81 °C (lit.)

General description

4(5)-Methylimidazole was quantified in coffee by GC-MS method[1].

pictograms

GHS05,GHS07

signalword

Danger

hcodes

H302 + H312,H314

pcodes

P260 - P280 - P301 + P312 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338

Hazard Classifications

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

Storage Class

8A - Combustible corrosive hazardous materials

wgk

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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Quantification of 4-methylimidazole in class III and IV caramel colors: validation of a new method based on heart-cutting two-dimensional liquid chromatography (LC-LC).

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

Microfluidic device capable of sensing ultrafast chemiluminescence.

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

Carcinogenic 4(5)-methylimidazole found in beverages, sauces, and caramel colors: chemical properties, analysis, and biological activities.

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

Formation of carcinogenic 4(5)-methylimidazole in Maillard reaction systems.

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)

Determination of 4(5)-methylimidazole in soy sauce and other foods by LC-MS/MS after solid-phase extraction.

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

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