Products

2-Methylimidazole

Product Introduction

2-Methylimidazole Basic information

Product Name:	2-Methylimidazole
Synonyms:	1H-Imidazole,2-methyl-;2-methyl-1h-imidazol;2-methyl-imidazol;2MZ;1H-2-MethyliMidazole;2MZ-H;2MZ-PW;Actiron 2MI
CAS:	693-98-1
MF:	C4H6N2
MW:	82.1
EINECS:	211-765-7
Product Categories:	Physisorption;Pharmaceutical intermediates;Alternative Energy;Materials for Hydrogen Storage;Cross-linker and Accelerator;Pyridines;Imidazol&Benzimidazole;Imidaxoles;Metal Organic Frameworks (MOFs);Organic Linker Molecules;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Materials Science;Imidazoles;Heterocyclic Compounds;693-98-1;bc0001
Mol File:	693-98-1.mol

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
pka	14.44±0.10(Predicted)
form	Crystalline Powder
color	White to light yellow
PH	10.5-11.5 (100g/l, H2O, 20℃)
PH Range	10.5
Water Solubility	Soluble in water and ethanol.
BRN	1368
InChIKey	LXBGSDVWAMZHDD-UHFFFAOYSA-N
LogP	0.22 at 25℃
CAS DataBase Reference	693-98-1(CAS DataBase Reference)
NIST Chemistry Reference	1H-Imidazole, 2-methyl-(693-98-1)
IARC	2B (Vol. 101) 2013
EPA Substance Registry System	2-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 Data	693-98-1(Hazardous Substances Data)
Toxicity	LD50 orally in Rabbit: 1500 mg/kg

MSDS Information

Provider	Language
2-Methylimidazole	English
SigmaAldrich	English
ACROS	English
ALFA	English

2-Methylimidazole Usage And Synthesis

Chemical Properties	2-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 Properties	The 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].
Uses	2-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.
Uses	2-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.
Preparation	2-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 Description	It 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.
Hazard	Possible carcinogen.
Flammability and Explosibility	Not classified
Purification Methods	Recrystallise 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.

2-Methylimidazole Preparation Products And Raw materials

Raw materials	Ammonia-->Acetonitrile-->Ethylenediamine-->Glyoxal-->Acetaldehyde-->2-METHYL-2-IMIDAZOLINE-->1,8-Diaminooctane-->Imidazole-2-carboxaldehyde-->1,12-Dodecanediamine-->2-METHYL-4(5)-IODO-1(H)-IMIDAZOLE
Preparation Products	Ondansetron-->5-BROMO-1,2-DIMETHYL-1H-IMIDAZOLE-->1,2-Dimethyl-5-nitroimidazole-->Metronidazole-->2-Methyl-5-nitroimidazole-->1-Benzyl-2-methyl-1H-imidazole-->2-Methyl-4-nitroimidazole-->1-(2-HYDROXYETHYL)-2-METHYLIMIDAZOLE-->Hexamethylenediamine

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