Imidazole

Catalog Number	ACM288324-5
CAS Number	288-32-4
Structure
Description	Imidazole is a biocompatible molecule that is used as a scaffold for biomimetic applications. It is used as a bioreagent with an ability to hydrogen bond with drugs and proteins. It can be also be used as an additive for the formation of an electrolyte for fuel cell applications.
Synonyms	Glyoxaline
IUPAC Name	1H-imidazole
Molecular Weight	68.08
Molecular Formula	C3H4N2
Canonical SMILES	C1=CN=CN1
InChI	InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
InChI Key	RAXXELZNTBOGNW-UHFFFAOYSA-N
Boiling Point	256 °C
Melting Point	88-91 °C
Flash Point	145 °C - closed cup
Purity	99%+
Density	Relative density (water = 1): 1.03;
Solubility	Very soluble in water;In water, 241 g/100 g at 20 deg C;In water, 2060 g/kg H₂O at 19 deg C;In water, 663 g/L at 20 deg C;Very soluble in ethanol; soluble in diethyl ether, acetone, pyridine; slightly soluble in benzene;Solubility in water, g/100ml at 20 °C: 63.3 (good);
Appearance	Crystalline
Application	Metal Plating, Electropolishing, Metal Reprocessing, Phase transfer media, Batteries Fuel Cells, Nanomaterials, Industrial Solvents, Nuclear Fuel Red Waste, Enzymatic Catalysis, Lubricants Heat Transfer and Solar Energy Conversion.
Storage	Store below +30 °C
EC Number	206-019-2
Exact Mass	68.037448136
Hydrogen-Bond Acceptor Count	1
Hydrogen-Bond Donor Count	1
Monoisotopic Mass	68.037448136
Odor	Amine-like odor;
pH	pH 10.5 for 38 g/L at 20 deg C;
Refractive Index	1.62
Rotatable-Bond Count	0
Specific Gravity	1.16
Topological Polar Surface Area	28.7 Ų

Case Study

Imidazole and 1,4-Butanediol Diglycidyl Ether Copolymer as an Efficient Suppressive Additive for Copper Electroplating

Hai, N. T. M., et al. Journal of the electrochemical society 161.9 (2014): D381.

A multifunctional suppressive additive (IBDGE) for copper electroplating was synthesized through the copolymerization of imidazole and 1,4-butanediol diglycidyl ether (BDGE). This novel copolymer contains ether, hydroxyl, and imidazolium functional groups, which are commonly found in polyalkylene glycol (PAG) suppressors and state-of-the-art leveling agent additives.
The IBDGE copolymer was synthesized based on the amine-epoxide reaction, using imidazole and 1,4-butanediol diglycidyl ether as reactants. Imidazole (0.1 mol) and BDGE (0.1 mol) were added to 200 mL of anhydrous ethanol in a round-bottom flask. The resulting solution was stirred at 60°C and 200 rpm for 6 hours. After the reaction was completed, the solvent was removed via rotary evaporation, and the product was dried overnight under a vacuum of 10⁻² mbar.

Structural Analysis of Polymer Contaminants in Electroplated Copper Films Using Imidazole-Containing Additive Packages

Moreno-García, Pavel, et al. Electrochimica Acta 199 (2016): 394-402.

Copper test samples were electrodeposited using a novel prototype dual-component additive package designed for advanced Damascene applications. This package consists of a mixed suppressive additive (Imep: a polymer of epichlorohydrin and imidazole) and its essential co-additive (SPS: sodium bis(3-sulfopropyl) disulfide). The tunable nonlinear interaction between Imep and SPS during oscillatory copper electrodeposition was utilized to produce samples with spatially confined layers featuring continuous high and edge additive incorporation.
These test samples provide an excellent platform for true quantitative chemical depth profile analysis of electrodeposited copper films. Specifically, LIMS (laser ionization mass spectrometry) depth profiling measurements, with unparalleled nanometer depth resolution, revealed that contaminants preferentially accumulate at grain boundaries within the copper deposits, while the copper grains themselves remain largely uncontaminated.
A novel LIMS desorption method was developed, enabling molecular structural analysis of the polymer additives preferentially embedded at the grain boundaries of the copper deposits. Our LIMS analysis supports recently discussed mechanisms of action for these mixed additives, which rely on their interaction with thiol salt-stabilized Cu(I) intermediates.

Two-Step Synthesis of IDZ-PE (Imidazole-Polyether) Suppressors

Han, Silin, et al. Electrochimica Acta 483 (2024): 144001.

In this study, a mixed additive IDZ-PE, composed of imidazole and polyether with varying degrees of polymerization, was designed and synthesized to investigate the intermolecular and intramolecular synergy between super-filling and leveling suppressors. Electrochemical tests and quantum calculations demonstrated that IDZ-PE possesses both super-filling and leveling capabilities. Moreover, void-free filling of vias was achieved using IDZ-PE, indicating its effectiveness as a suppressor for copper electrodeposition in vias.
Two-Step Synthesis of IDZ-PE Suppressors
The synthesis involved two reaction steps. First, tosyl-terminated polyethylene glycol (PEG) with varying degrees of polymerization was synthesized via tosylation of PEG to produce polymers with "tail" groups of different lengths. Second, IDZ-PE was synthesized by reacting Ots-PEG, cetyltrimethylammonium bromide (CTAB), NaOH, 1H-imidazole, and toluene, forming an imidazole "head" group for the polymer.
Three types of IDZ-PE with different degrees of polymerization were synthesized: 7, 45, and 113, featuring tail groups with molecular weights of 350 g/mol, 2000 g/mol, and 5000 g/mol, respectively. Based on their molecular weights, the suppressors were designated as M350, M2000, and M5000. Corresponding mixtures with the same degree of polymerization as IDZ-PE, represented as IDZ+PE, were named IP350, IP2000, and IP5000, respectively.

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