20185-22-2

Basic information

• Product Name: 1,4,5-Trimethyl-1H-imidazole
• Synonyms: 1,4,5-Trimethyl-1H-imidazole;1,4,5-Trimethylimidazole
• CAS NO: 20185-22-2
• Molecular Formula: C₆H₁₀N₂
• Molecular Weight: 110
• Mol File: 20185-22-2.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 242℃
• Flash Point: 100℃
• Appearance: /
• Density: 0.97
• Vapor Pressure: 0.0552mmHg at 25°C
• Refractive Index: 1.514
• PKA: 7.92±0.61(Predicted)
• CAS DataBase Reference: 1,4,5-Trimethyl-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,5-Trimethyl-1H-imidazole(20185-22-2)
• EPA Substance Registry System: 1,4,5-Trimethyl-1H-imidazole(20185-22-2)

Safety Data

• Hazardous Substances Data: 20185-22-2(Hazardous Substances Data)

Usage

General Description

1,4,5-Trimethyl-1H-imidazole, also known as TMIO or TMI, is a chemical compound with the molecular formula C6H10N2. It is a derivative of imidazole and is classified as a substituted imidazole. TMIO is a colorless liquid at room temperature and is soluble in water and most organic solvents. It is commonly used as a corrosion inhibitor in metalworking fluids and as a stabilizer for halogenated solvents. TMIO also has pharmaceutical applications, as it is an intermediate in the synthesis of various pharmaceutical compounds. Furthermore, it has been studied for its potential use in organic synthesis and as a reagent in biochemical research. Overall, 1,4,5-Trimethyl-1H-imidazole has a variety of industrial and scientific applications due to its unique chemical properties.

InChI:InChI=1/C6H10N2/c1-5-6(2)8(3)4-7-5/h4H,1-3H3

Upstream product

• 50-00-0 formaldehyd 
• 431-03-8 dimethylglyoxal 
• 74-89-5 methylamine 
• 63455-73-2 1,4,5-trimethyl-1H-imidazole 3-oxide 
• 512-42-5 sodium methyl sulfate 
• 593-51-1 methylamine hydrochloride 
• 2302-39-8 4,5-dimethylimidazole 
• 74-88-4 methyl iodide 

Downstream Products

• 25812-77-5 1,2,3,4,5-pentamethyl-1H-imidazol-3-ium iodide 
• 152536-39-5 1,4,5-Trimethyl-2-phenylimidazole 
• 1207454-70-3 ethyl 2-(4-fluorophenyl)-4-oxo-3-(1,4,5-trimethyl-1H-imidazol-2-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate 
• 1207454-69-0 8-(4-fluorophenyl)-9-(1,4,5-trimethyl-1H-imidazol-2-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one 
• 618442-71-0 1,4,5-trimethylimidazole-tris(pentafluorophenyl)borane adduct 
• 185910-12-7 1,4,5-trimethyl-1H-imidazole-2-carbaldehyde 
• 185910-13-8 (1,4,5-Trimethyl-1H-imidazol-2-yl)-methanol 

Relevant articles and documents

ELECTRONIC STRUCTURE OF ALKYLATED IMIDAZOLES AND ELECTRONIC SPECTRA OF TETRAKIS(IMIDAZOLE)COPPER(II) COMPLEXES. MOLECULAR STRUCTURE OF TETRAKIS(1,4,5-TRIMETHYLIMIDAZOLE)COPPER(II) DIPERCHLORATE.

The synthesis, crystal structure, electronic spectra, and ESR spectra are reported for the title complex (1). Energies of the molecular orbitals and electronically excited states of imidazole and of several methylated imidazoles have been calculated. Ligand to metal charge-transfer (LMCT) absorptions of the title complex and other Cu(II)-imidazole complexes are discussed and compared. preliminary LMCT spectra are presented for the yellow diamagnetic tetrakis(1,2-dimethylimidazole)nickel(II) diperchlorate complex and its Cu(II) analogue. An experimental justification for assigning the charge-transfer absorptions as LMCT instead of MLCT is presented.

Syntheses of polyalkylated imidazoles

We have developed improved general simple methods for large-scale preparation of polyalkylated imidazoles by improved multicomponent synthesis from commercially available starting materials. A large range of NH- and N-alkyl-polyalkylimidazoles (40 in total, including novel compounds) has been synthesized.

Asymmetric Copper(II)-catalysed nitroaldol (Henry) reactions utilizing a chiral C1-symmetric dinitrogen ligand

A series of stable chiral C1-symmetric dinitrogen ligands were conveniently synthesized in high yields by condensation of chiral amines [(-)-exo-bornylamine or (+)-(1S,2S,5R)-menthylamine] with various substituted imidazolecarbaldehydes. With the assistance of base, the ligand L1 in combination with CuCl2·2H2O (2.5 mol-% or 5.0 mol-%) can efficiently promote nitroaldol (Henry) reactions between a variety of aldehydes and nitromethane. Both aromatic and aliphatic aldehydes were tolerated in our catalytic system, affording the expected nitroalcohol products in high yields (up to 97%) and with good enantioselectivities (up to 96%) under mild reaction conditions. A series of chiral C1-symmetric dinitrogen ligands were conveniently synthesized in high yields by condensations of chiralamines with various substituted imidazolecarbaldehydes. The ligand L1 in conjunction with CuCl2·2H2O can efficiently promote nitroaldol (Henry) reactions between various aldehydes and nitromethane in high yields (up to 97%) and with good enantioselectivities (up to 96%).