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4-Methylimidazole

Product Name
4-Methylimidazole
CAS No.
822-36-6
Chemical Name
4-Methylimidazole
Synonyms
4-methyl-1h-imidazole;5-Methyl-1H-imidazole;1H-Imidazole, 4-methyl-;Methyl-1H-imidazole;4(5)-METHYLIMIDAZOLE;4-Me-i;NSC 40744;1H-Imidaz;4-MethyliMidaz;4-methyl-imidazol
CBNumber
CB5424070
Molecular Formula
C4H6N2
Formula Weight
82.1
MOL File
822-36-6.mol
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4-Methylimidazole Property

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)
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
199885
Product name
4(5)-Methylimidazole
Purity
98%
Packaging
50g
Price
$69.7
Updated
2024/03/01
Sigma-Aldrich
Product number
04535
Product name
4(5)-Methylimidazole
Purity
analytical standard
Packaging
100mg
Price
$80.1
Updated
2022/05/15
TCI Chemical
Product number
M0636
Product name
4-Methylimidazole
Purity
>98.0%(GC)
Packaging
25g
Price
$38
Updated
2024/03/01
TCI Chemical
Product number
M0636
Product name
4-Methylimidazole
Purity
>98.0%(GC)
Packaging
100g
Price
$93
Updated
2024/03/01
Alfa Aesar
Product number
B24139
Product name
4-Methylimidazole, 98%
Packaging
10g
Price
$24.65
Updated
2024/03/01
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4-Methylimidazole Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Methylglyoxal Formaldehyde Ammonium oxalate Methanol Ammonia

Preparation Products

4-[[(2-aminoethyl)thio]methyl]-5-methylimidazole Cimetidine
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4-Methylimidazole Suppliers

Americas 1 Belgium 2 Canada 2 China 500 Europe 2 France 2 Germany 7 India 15 Japan 3 Slovakia 1 South Korea 1 Switzerland 3 The Netherlands 1 Ukraine 1 United Kingdom 11 United States 39 Global 591
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View Lastest Price from 4-Methylimidazole manufacturers

Jinan Finer Chemical Co., Ltd
Product
4-Methylimidazole 822-36-6
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
99%
Supply Ability
200mt/year
Release date
2021-09-03
Hebei Longbang Technology Co., Ltd
Product
4-Methylimidazole 822-36-6
Price
US $3.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20TONS
Release date
2024-04-30
Ningxia Jinhua Chemical Co.,Ltd
Product
4-Methylimidazole 822-36-6
Price
US $0.00/Kg/Drum
Min. Order
25Kg/Drum
Purity
98
Supply Ability
1mt
Release date
2020-10-19

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