4-Methylimidazole Chemical Properties

Melting point:

44-47 °C(lit.)

Boiling point:

263 °C(lit.)

Density 

1.02

refractive index 

1.5037

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

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

form 

Powder

pka

pK1:7.55(＋1) (25°C)

color 

Reddish-brown to green to brown

Water Solubility 

Soluble in water.

BRN 

1453

InChIKey

XLSZMDLNRCVEIJ-UHFFFAOYSA-N

LogP

0.230

CAS DataBase Reference

822-36-6(CAS DataBase Reference)

NIST Chemistry Reference

4-Methylimidazole(822-36-6)

IARC

2B (Vol. 101) 2013

EPA Substance Registry System

1H-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 Data

822-36-6(Hazardous Substances Data)

MSDS

• Language:English Provider:4-Methylimidazole
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
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4-Methylimidazole Usage And Synthesis

Chemical Properties

Slightly yellow chunks. soluble in water and ethanol.

Uses

4-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.

Uses

4-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.

Preparation

4-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).

Definition

ChEBI: 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 Description

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

Biological Activity

4-Methylimidazole forms complexes with heme-containing enzymes such as cytochrome P450 (CYP) and leads to inhibition of mixed-function oxidase activity. 4-Methylimidazole has been reported to significantly inhibit CYP2E1 activity in rat liver and toluenesulfonylurea hydroxylase (CYP2C9) activity in human and rat microsomes. In addition, it stimulated phosphorylation of rabbit kidney (Na and K)-adenosine triphosphatase and exhibited significant antioxidant activity in a lipid peroxyl radical activity capture assay.

Side effects

4-Methylimidazole is an eye irritant, causes burns, may cause corrosive damage to the upper respiratory tract and lungs if inhaled, and is harmful if ingested.
In vivo findings: No histopathological changes were observed in 15-day oral studies in rats and mice. A 14-week oral study showed tremors, ataxia, anaemia, vacuolisation of hepatocytes and testicular degeneration in rats and anaemia, vacuolisation of hepatocytoplasm and renal degeneration in mice.
Histopathological liver changes were also observed in a 106-week oral study in rats, causing neurological effects including hyperexcitability, convulsions and seizures in livestock and experimental animals. Reproductive organ toxicity and reduced fertility were observed in male rats.
Evidence of carcinogenicity: no carcinogenicity in male rats; ambiguous in female rats; clear evidence in male and female mice; irritating or corrosive to rabbit skin.

Purification Methods

Recrystallise 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.]

4-Methylimidazole(822-36-6)Related Product Information

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