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2-Methylimidazole

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CAS:693-98-1
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2-Methylimidazole Basic information
Product Name:2-Methylimidazole
Synonyms:2-Methylimidazole,97%;RESICURE(TM) 46;2-METHYLIMIDAZOLE pure;2-MethyliMidazole, 99% 100GR;2-MethyliMidazole, 99% 500GR;Curezol 2MZ;Denka CN 25;2-Methylimidazole,99%
CAS:693-98-1
MF:C4H6N2
MW:82.1
EINECS:211-765-7
Product Categories:Physisorption;Pharmaceutical intermediates;Pyridines;Cross-linker and Accelerator;Alternative Energy;Materials for Hydrogen Storage;Metal Organic Frameworks (MOFs);Organic Linker Molecules;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Materials Science;Imidaxoles;Imidazol&Benzimidazole;Imidazoles;Heterocyclic Compounds;693-98-1;bc0001
Mol File:693-98-1.mol
2-Methylimidazole Structure
2-Methylimidazole Chemical Properties
Melting point 142-143 °C (lit.)
Boiling point 267-268 °C (lit.)
density 1.0500 (rough estimate)
vapor pressure <1 mm Hg ( 0 °C)
refractive index 1.4970 (estimate)
Fp 155 °C
storage temp. 2-8°C
solubility 780g/l
form Crystalline Powder
pka14.44±0.10(Predicted)
color White to light yellow
PH10.5-11.5 (100g/l, H2O, 20℃)
PH Range10.5
Water Solubility Soluble in water and ethanol.
BRN 1368
InChIKeyLXBGSDVWAMZHDD-UHFFFAOYSA-N
LogP0.22 at 25℃
CAS DataBase Reference693-98-1(CAS DataBase Reference)
IARC2B (Vol. 101) 2013
NIST Chemistry Reference1H-Imidazole, 2-methyl-(693-98-1)
EPA Substance Registry System2-Methylimidazole (693-98-1)
Safety Information
Hazard Codes C
Risk Statements 22-34
Safety Statements 26-36/37/39-45-25
RIDADR UN 3259 8/PG 2
WGK Germany 2
RTECS NI7175000
Autoignition Temperature>600 °C DIN 51794
Hazard Note Harmful/Corrosive
TSCA Yes
HazardClass 8
PackingGroup III
HS Code 29332990
Hazardous Substances Data693-98-1(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 1500 mg/kg
MSDS Information
ProviderLanguage
2-Methylimidazole English
SigmaAldrich English
ACROS English
ALFA English
2-Methylimidazole Usage And Synthesis
Chemical Properties2-Methylimidazole is a white to light yellow crystalline powder with an amine-like odor. It is highly soluble in polar organic solvents. Insoluble in ether and cold benzene, easily soluble in water, alcohols and ketones. Irritating to skin and mucous membranes. Mice orally LD50 1400mg/kg.
Chemical PropertiesThe 2-methylimidazole molecule is approximately planar, and the maximum deviation of all non-H atoms from the plane of the least squares imidazole is 0.006(2)?. N–H··· N hydrogen bonds link molecules together to form infinite chains of hydrogen bond pattern C(4). The crystal of 2-methylimidazole is in orthorhombic crystal system with space group P212121 (Z = 4), lattice parameters: a = 5.9957(12) ?, b = 8.1574(16) ? and c = 9.7010(19) ?, V = 474.47(16) ?[1].
Uses2-Methylimidazole is used as a raw material for the preparation of nitroimidazole antibiotics, which is useful in combat anaerobic bacterial and parasitic infections. It acts as a ligand in coordination chemistry. It is also employed as a hardener or accelerator for epoxy resin and auxiliary agent for textile dyes. Further, it acts as a catalyst for refolding of enhanced colored fluorescent protein. It is also useful as a building block in the synthesis of biologically active compounds. In addition to this, it is used as an active pharmaceutical ingredient intermediate such as metronidazole and dimetridazole.
Uses2-Methylimidazole is a monomethylated imidazole that can be used as a building block in the preparation of a wide range of biologically active compounds. 2-Methylimidazole as well as other imidazoles can be use as catalyst for refolding of enhanced coloured fluorescent protein. 2-Methylimidazole has been identified as a byproduct of fermentation and is detected in foods and mainstream and side-str eam tobacco smoke.
Preparation2-Methylimidazole is prepared by condensation of glyoxal, ammonia and acetaldehyde, a Radziszewski reaction. It is widely used as a polymeriza tion cross-linking accelerator and a hardener for epoxy resin systems for semiconductor potting compounds and soldering masks.
It is obtained by eliminating dehydrogenation of 2-methylimidazoline. 2-methylimidazoline heated to melt (melting point 107 ℃), carefully add active nickel, raise the temperature to 200-210 ℃ reaction 2h. cool down to below 150 ℃, add water to dissolve, while hot pressure filtration, separation of active nickel, the filter Chemicalbook liquid concentrated to a temperature of 140 ℃ or more, put the material cooling that 2-methylimidazole. Use the method to produce purity of ≥ 98% of the product, 1t product consumption of ethylenediamine (95%) 1095kg, acetonitrile 975kg. better method is to use glyoxal and aldehyde as raw materials.
General DescriptionIt is a white or colorless solid that is highly soluble in polar organic solvents and water. It is a precursor to a range of drugs and is a ligand in coordination chemistry.
HazardPossible carcinogen.
Flammability and ExplosibilityNot classified
Purification MethodsRecrystallise 2-methylimidazole from *benzene or pet ether. The picrate has m 215o (from H2O). [Beilstein 23 III/IV 594, 23/5 V 35.]
References[1] Hachu?a B, et al. Crystal and Molecular Structure Analysis of 2-Methylimidazole. Journal of Chemical Crystallography, 2009; 40: 201–206.
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