4-Methylimidazole

4-Methylimidazole Basic information
Product Name:4-Methylimidazole
Synonyms:1H-Imidazole, 4-methyl-;1H-Imidazole,4-methyl;4(5)-Methylglyoxaline;4(Or 5)-Methylimidazole;4-Me-i;4-methyl-1(3)H-imidazole;4-methyl-1h-imidazol;NSC 40744
CAS:822-36-6
MF:C4H6N2
MW:82.1
EINECS:212-497-3
Product Categories:Building Blocks;Chemical Synthesis;Building Blocks;Heterocyclic Building Blocks;Imidazoles;Heterocyclic Building Blocks;Imidazol&Benzimidazole;Miscellaneous;Imidaxoles;bc0001;822-36-6
Mol File:822-36-6.mol
4-Methylimidazole Structure
4-Methylimidazole Chemical Properties
Melting point 44-47 °C(lit.)
Boiling point 263 °C(lit.)
density 1.02
refractive index 1.5037
Fp >230 °F
storage temp. 2-8°C
solubility H2O: soluble, clear, colorless to yellow (50 mg/mL)
form Powder
pkapK1:7.55(+1) (25°C)
color Reddish-brown to green to brown
Water Solubility Soluble in water.
BRN 1453
InChIKeyXLSZMDLNRCVEIJ-UHFFFAOYSA-N
LogP0.230
CAS DataBase Reference822-36-6(CAS DataBase Reference)
NIST Chemistry Reference4-Methylimidazole(822-36-6)
IARC2B (Vol. 101) 2013
EPA Substance Registry System1H-Imidazole, 4-methyl- (822-36-6)
Safety Information
Hazard Codes C
Risk Statements 21/22-34-22
Safety Statements 26-36/37/39-45-25
RIDADR UN 3263 8/PG 3
WGK Germany 2
RTECS NI7350000
TSCA Yes
HazardClass 8
PackingGroup III
HS Code 29339900
Hazardous Substances Data822-36-6(Hazardous Substances Data)
MSDS Information
ProviderLanguage
4-Methylimidazole English
ACROS English
SigmaAldrich English
ALFA English
4-Methylimidazole Usage And Synthesis
Chemical PropertiesSlightly yellow chunks. soluble in water and ethanol.
Uses4-Methylimidazole is a monomethylated imidazole that can be used as a building block in the preparation of a wide range of biologically active compounds. 4-Methylimidazole is a product which results f rom the interaction of reducing sugars with ammonia. 4-Methylimidazole showed convulsant activity in animals and is listed as a possible carcinogen.
Uses4-Methylimidazole is used for the curing agent of epoxy resin, the main raw material of medicine cimetidine. It can also be used for synthesis of antibacterial agent.
Preparation4-Methylimidazole is synthesized by the reaction of glyoxal, acetaldehyde and ammonia. Another method to synthesize the compound is by catalytic dehydrogenation of imidazoline derivatives. 4-Methylimidazole may be synthesized from propanol and formamide, by catalytic cyclization of bisformamidipropane or by photolysis of alkenyltetrazole derived from alkenes by sequential epoxidation, ring opening and dehydration (NTP, 2007).
DefinitionChEBI: 4-methylimidazole is imidazole substituted at position 4 by a methyl group. It has a role as a carcinogenic agent and a reaction intermediate.
General Description4(5)-Methylimidazole was quantified in coffee by GC-MS method.
Purification MethodsRecrystallise 4-methylimidazole from *benzene or pet ether. It has m 56o after sublimation. The picrate has m 162-163.5o (from EtOH). [Beilstein 23 II 60, 23 III/IV 597, 23/5 V 89.]
Methylparaben Methyl 1-Methylimidazole 2-Ethyl-4-methylimidazole Acetonitrile Levamisole Midazolam Basic Violet 1 4-Methylimidazole 1H-Imidazole-4-carboxylic acid 2-Methylimidazole Kresoxim-methyl Imidazole Vinylimidazole Levamisole hydrochloride Methanol Methyl acrylate Mebendazole

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