1-METHYLIMIDAZOLE

1-METHYLIMIDAZOLE

PRODUCT IDENTIFICATION

CAS NO.

616-47-7

1-METHYLIMIDAZOLE

EINECS NO.

210-484-7

FORMULA

C₄H₆N₂

MOL WT.

82.12

H.S. CODE

2933.29.9090

TOXICITY

Mouse LD50 (Oral) 1400mg/kg

SYNONYMS

N-Methylimidazole; 1-Methyl-1H-Imidazole; Methyl Imidazole;

Other RN: 69723-05-3; 110069-11-9; 120418-32-8; 142504-34-5; 674282-80-5; 864745-22-2; 955156-62-4

SMILES

n1(ccnc1)C

CLASSIFICATION

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE

Clear to slightly yellow liquid

MELTING POINT

-60 C

BOILING POINT

198 C

SPECIFIC GRAVITY

1.03

SOLUBILITY IN WATER

miscible (1.00E+06 mg/l)

VAPOR DENSITY

2.83

AUTOIGNITION

524 C

pKa

6.95 (at 25 C)

log Pow

-0.08 (Octanol-water)

VAPOR PRESSURE

0.478 (mmHg)

HENRY'S LAW

8.01E-05 (atm-m3/mole at 25 C)

3.61E-11 (cm3/molecule-sec at 25 C Atmospheric)

NFPA RATINGS

REFRACTIVE INDEX

1.4960

FLASH POINT

92 C

STABILITY

Stable under ordinary conditions

GENERAL DESCRIPTION & EXTERNAL LINKS

N-Methylimidazole is used as an intermediate for pharmaceuticals, agrochemicals, dyes, textile auxiliaries, pigments and other organic chemicals. It is also used in polyurethane manufacturing and epoxy resins as a curing agent.

Wikipedia Linking:http://en.wikipedia.org/wiki/1-Methylimidazole

http://www.rsc.org
A simple colorimetric method to monitor the production of ionic liquid precursors is developed, which is based on the determination of 1-methylimidazole with copper(II) chloride. The synthesis of 1-ethyl-3-methylimidazolium chloride, an industrially important ionic liquid precursor, can be followed and the purity of the final product can be readily assessed in a quick and convenient manner........

http://www.wag.caltech.edu/
Group III alkyl complexes supported by a ferrocene diamide ligand (1,1��-fc(NSitBuMe2)2) have been found to be reactive toward aromatic N-heterocycles such as 1-methylimidazole and pyridines. These reactions were investigated experimentally and computationally. An initial C-H activation event is followed by a coupling reaction to form biheterocyclic complexes, in which one of the rings is dearomatized. In the case of 1-methylimidazole, the biheterocyclic compound could not be isolated and further led to an imidazole ring-opened product; in the case of pyridines, it transformed into an isomer with extended conjugation of double bonds. Mechanisms for both reactions are proposed on the basis of experimental and computational results. DFT calculations were also used to show that an energetically accessible pathway for the ringopening of pyridines exists.....

http://www.sigmaaldrich.com
1-Methylimidazole is a derivative of imidazole that is utilized in the manufacture of such classes of items as pharmaceuticals, pesticides, ion-exchange resins, dye intermediates, textile auxiliaries, photographic chemicals, and corrosion inhibitors. It is also used as a catalyst for manufacturing polyurethanes and a curing agent for epoxy resins. 1-Methylimidazole has been utilized in the synthesis of inorganic complexes, ionic liquids, and catalytic deprotonation reagents. The use of 1-methylimidazole in the preparation of GDP-hexanolamine for the purification of fucosyltransferases has been reported.....

SALES SPECIFICATION

APPEARANCE

Clear to yellow liquid

ASSAY

99.0% min

WATER

0.5% max

TRANSPORTATION

PACKING

200kgs in drum

HAZARD CLASS

8 (Packing group:III)

UN NO.

3267

DESCRIPTION OF IMIDAZOLE

Imidazole is a heterocyclic compound of five-membered diunsaturated ring structure composed of three carbon atoms and two nitrogen atoms at nonadjacent positions. The simplest member of the imidazole family is imidazole itself, colorless to pale yellow crystalline solid with a weak aminelike odor; soluble in water and alcohol, melts at 89 C, boils at 256 C. Imidazoles are poorly soluble in water generally, but are dissolved in organic solvents, such as chloroform, propylene glycol, and polyethoxylated castor oil. Imidazole ring is found in histidine (an essential amino acid) and histamine, the decarboxylated compound from histamine. Some imidazole compounds inhibit the biosynthesis of ergosterol, required in cell membrane in fungal. They have antibacterial, antifungal, antiprotozoal, and anthelmintic activity. Several distinct phenylimidazoles are therapeutically useful antifungal agents against either superficial or systemic infections. Thiabendazoles which have anthelmintic and antifungal properties are imidazole class compounds. Benzimidazole is a dicyclic compound having midazole ring fused to benzene. Benzimidazole structure is a part of the nucleotide portion of vitamin B₁₂ and the nucleus in some drugs such as proton pump inhibitors and anthelmintic agents. Imidazole has two nitrogen atoms. The one is slightly acidic, while the other is basic. Imidazole and its derivatives are widely used as intermediates in synthesis of organic target compounds including pharmaceuticals, agrochemicals, dyes, photographic chemicals, corrosion inhibitors, epoxy curing agents, adhesives and plastic modifiers. Some imidazole analogues which contain nitrogen in five-membered ring structure are:

Triazole: An analog of imidazole.It has three nitrogen atoms and two carbon atoms at nonadjacent positions in the ring system.
Pyrrole: An analog of imidazole. It has only one nitrogen atom in the ring system. Pyrrole ring system is involved in coloured products (green pigment, chlorophyll; red, hemoglobin; , blue, indigo) in nature.
Pyrroline: A pyrrole in which one of the two solid bonds are hydrogenated.
Pyrrolidine: The saturated tetrahydropyrrole, a part of the structures of amino acids (proline, hydroxyproline and hygrine).
Pyrazole: 1,2-Diazole (Imidazole isomer). The nitrogen positions are 1 and 2. It is not found in nature
Pyrazolone: Pyrazole analog with ketone group at 5 positon
Oxazole: an analog of imidazole. The nitrogen atom in position 1 is replaced by oxygen.
Isoxazole: an analog of pyrazole. The nitrogen atom at position 1 is replaced by oxygen.
Isothiazole:an analog of pyrazole. The nitrogen atom at position 1 is replaced by sulfur.


1,2,4-Triazole	Pyrrole	1-Pyrroline	3-Pyrroline

Pyrrolidine	Pyrazole	Pyrazolone	Oxazole

Isoxazole	Isothiazole	Benzimidazole	Thiabendazole