| Identification | More | [Name]
2-Methylimidazole-4-sulfonic acid | [CAS]
822-36-6 | [Synonyms]
4(5)-METHYLIMIDAZOLE
4-methyl-1h-imidazole
4-METHYLIMIDAZOLE
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
4-methyl-imidazol
5-Methyl-1H-imidazole
5-Methylimidazole
Imidazole, 4-methyl-
4-Methylimidazole,98% | [EINECS(EC#)]
212-497-3 | [Molecular Formula]
C4H6N2 | [MDL Number]
MFCD00005201 | [Molecular Weight]
82.1 | [MOL File]
822-36-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Slightly yellow chunks | [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 | [pka]
pK1:7.55(＋1) (25°C) | [color ]
Reddish-brown to green to brown | [Water Solubility ]
Soluble in water. | [Detection Methods]
GC,NMR | [BRN ]
1453 | [InChIKey]
XLSZMDLNRCVEIJ-UHFFFAOYSA-N | [LogP]
0.230 | [CAS DataBase Reference]
822-36-6(CAS DataBase Reference) | [IARC]
2B (Vol. 101) 2013 | [NIST Chemistry Reference]
4-Methylimidazole(822-36-6) | [Storage Precautions]
Store under nitrogen | [EPA Substance Registry System]
822-36-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R21/22:Harmful in contact with skin and if swallowed .
R34:Causes burns.
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S25:Avoid contact with eyes . | [RIDADR ]
UN 3263 8/PG 3
| [WGK Germany ]
2
| [RTECS ]
NI7350000
| [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29332900 | [Hazardous Substances Data]
822-36-6(Hazardous Substances Data) |
| Hazard Information | Back Directory | [Chemical Properties]
Slightly yellow chunks | [Uses]
4-Methylimidazole(822-36-6) 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]
2-Methylimidazole-4-sulfonic acid can be used as antineoplastic
| [Definition]
ChEBI: Imidazole substituted at position 4 by a methyl group. | [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). | [General Description]
4(5)-Methylimidazole was quantified in coffee by GC-MS method. | [Biological Activity]
4-Methylimidazole(822-36-6) 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(822-36-6) 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.] |
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