1192-53-6

Basic information

• Product Name: 4,5-DICHLORO-1-METHYLIMIDAZOLE
• Synonyms: 4,5-dichloro-1-methyl-1H-imidazole;4,5-DICHLORO-1-METHYLIMIDAZOLE;BUTTPARK 121\04-73
• CAS NO: 1192-53-6
• Molecular Formula: C₄H₄Cl₂N₂
• Molecular Weight: 150.99
• Mol File: 1192-53-6.mol

Chemical Properties

• Melting Point: 53-55°C
• Boiling Point: 286.8°Cat760mmHg
• Flash Point: 127.2°C
• Appearance: /
• Density: 1.49g/cm³
• Vapor Pressure: 0.00446mmHg at 25°C
• Refractive Index: 1.595
• Water Solubility: Soluble in water.
• CAS DataBase Reference: 4,5-DICHLORO-1-METHYLIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-DICHLORO-1-METHYLIMIDAZOLE(1192-53-6)
• EPA Substance Registry System: 4,5-DICHLORO-1-METHYLIMIDAZOLE(1192-53-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 1192-53-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
4,5-Dichloro-1-methylimidazole is used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique chemical structure allows it to be a key component in the development of new drugs and pesticides, contributing to advancements in healthcare and agriculture.
Used in Polyurethane Foam Production:
4,5-Dichloro-1-methylimidazole serves as a stabilizer in the production of polyurethane foam. Its presence helps to maintain the desired properties of the foam, such as its flexibility, durability, and resistance to degradation, making it suitable for various applications, including furniture, bedding, and insulation materials.
Used in Water Treatment as a Corrosion Inhibitor:
In the water treatment industry, 4,5-dichlor0-1-methylimidazole is utilized as a corrosion inhibitor. It helps to prevent the corrosion of metal surfaces in contact with water, thereby extending the lifespan of pipelines, storage tanks, and other water handling equipment. This application is particularly important in industries that rely on water for their processes, such as power generation, oil and gas, and chemical manufacturing.

InChI:InChI=1/C4H4Cl2N2/c1-8-2-7-3(5)4(8)6/h2H,1H3

Upstream product

• 15965-30-7 4,5-dichloroimidazole 
• 74-88-4 methyl iodide 

Downstream Products

• 1258870-78-8 4,5-dichloro-1-methyl-3-benzylimidazolium bromide 
• 1307297-20-6 4,5-dichloro-1-methyl-3-(4-nitrobenzyl)imidazolium bromide 

Relevant articles and documents

[(NHC)(NHCewg)RuCl2(CHPh)] complexes with modified NHCewg ligands for efficient ring-closing metathesis leading to tetrasubstituted olefins

Imidazolium salts (NHCewg-HCl) with electronically variable substituents in the 4,5-position (H,H or C1,C1 or H,NO2 or CN 5CN) and sterically variable substituents in the 1,3-position (Me,Me or Et,Et or iPr,iPr or Me,iPr) were synthesized and converted into the respective [AgI(NHC)ewg] complexes. The reactions of [(NHC)RuCl 2(CHPh)(Py)2] with the [AgI(NHQw8)] complexes provide the respective [(NHC)(NHCewg)RuCl2(CHPh)] complexes in excellent yields. The catalytic activity of such complexes in ring-closing metathesis (RCM) reactions leading to tetrasubstituted olefins was studied. To obtain quantitative substrate conversion, catalyst loadings of 0.2-0.5 mol% at 80°C in toluene are sufficient. The complex with the best catalytic activity in such RCM reactions and the fastest initiation rate has an NHCewg group with l,3-Me,iPr and 4,5-Cl,Cl substituents and can be synthesized in 95 % isolated yield from the ruthenium precursor. To learn which one of the two NHC ligands acts as the leaving group in olefin metathesis reactions two complexes, [(FL-NHC)-(NHCcwg)RuCl2(CHPh)] and [(FLNHCewg)(NHC)RuCl2(CHPh)], with a dansyl fluorophore (FL)-tagged electron-rich NHC ligand (FL-NHC) and an electron-deficient NHC ligand (FLNHCewg) were prepared. The fluorescence of the dansyl fluorophore is quenched as long as it is in close vicinity to ruthenium, but increases strongly upon dissociation of the respective fluorophore-tagged ligand. In this manner, it was shown for ring-opening metathesis ploymerization (ROMP) reactions at room temperature that the NHCewg ligand normally acts as the leaving group, whereas the other NHC ligand remains ligated to ruthenium.

Synthesis, stability, and antimicrobial studies of electronically tuned silver acetate N-heterocyclic carbenes

A series of methylated imidazolium salts with varying substituents on the 4 and 5 positions of the imidazole ring were synthesized. These salts were reacted with silver acetate to afford their corresponding silver N-heterocyclic carbene (NHC) complexes. These complexes were then evaluated for their stability in water as well as for their antimicrobial efficacy against a variety of bacterial strains associated with cystic fibrosis and chronic lung infections.

Novel Chloroimidazolium-Based Ionic Liquids: Synthesis, Characterisation and Behaviour as Solvents to Control Reaction Outcome

Novel ionic liquids containing chlorine atoms on the imidazolium cation were synthesised. The physicochemical properties of these ionic liquids were investigated extensively, including glass transition, melting and decomposition temperatures, density, vis

Synthesis, cytotoxicity and antibacterial studies of novel symmetrically and non-symmetrically p-nitrobenzyl-substituted N-heterocyclic carbene-silver(i) acetate complexes

From the reaction of 1H-imidazole (1a), 4,5-dichloro-1H-imidazole (1b), 1H-benzimidazole (1c), 1-methylimidazole (1d), 4,5-dichloro-1-methylimidazole (1e) and 1-methylbenzimidazole (1f) with p-nitrobenzyl bromide (2), symmetrically and non-symmetrically p

Synthesis, cytotoxicity and antibacterial studies of symmetrically and non-symmetrically benzyl- or p-cyanobenzyl-substituted N-Heterocyclic carbene - Silver complexes

From the reaction of 1H-imidazole (1a), 4,5-dichloro-1H-imidazole (1b) and 1H-benzimidazole (1c) with p-cyanobenzyl bromide (2), symmetrically substituted N-heterocyclic carbene (NHC) [(3a-c)] precursors, 1-methylimidazole (5a), 4,5-dichloro-1-methylimida

Estimated rate constants for hydrogen abstraction from n-heterocyclic carbene-borane complexes by an alkyl radical

Rate constants for hydrogen abstraction by a nonyl radical from 20 complexes of N-heterocyclic carbenes and boranes (NHC-boranes) have been determined by the pyridine-2-thioneoxycarbonyl (PTOC) competition kinetic method at a single concentration point. The rate constants range from 4 to 8 × 104 M-1 s-1. They show little dependence on the electronic properties of the carbene core, but there is a trend for increasing rate constants with decreasing size of the carbene N-substituents. Two promising new reagents with small N-substituents (R = Me) have been identified.