6923-01-9

Basic information

• Product Name: IMIDAZOLE-D4
• Synonyms: IMIDAZOLE-D4;Imidazole-d4,98 atom %D;IMIDAZOLE-D4, 95 ATOM % D;1H-Imidazole-1,2,4,5-d4;1H-Imidazole;Imidazole-d4;1,2,4,5-tetradeuterioimidazole
• CAS NO: 6923-01-9
• Molecular Formula: C₃H₄N₂
• Molecular Weight: 72.1
• Product Categories: Alphabetical Listings;Biomolecular NMR;Buffers and ReagentsStable Isotopes;I-LStable Isotopes;NMR - Buffers and Reagents;NMR Solvents and Reagents;Stable Isotopes;Aromatics;Heterocycles;Intermediates;Isotope Labelled Compounds
• Mol File: 6923-01-9.mol

Chemical Properties

• Melting Point: 89-91 °C(lit.)
• Boiling Point: 256 °C(lit.)
• Flash Point: 145℃
• Appearance: /
• Density: 1.182 g/cm³
• Vapor Pressure: 0.024mmHg at 25°C
• Refractive Index: 1.528
• PKA: 6.953(at 25℃)
• CAS DataBase Reference: IMIDAZOLE-D4(CAS DataBase Reference)
• NIST Chemistry Reference: IMIDAZOLE-D4(6923-01-9)
• EPA Substance Registry System: IMIDAZOLE-D4(6923-01-9)

Safety Data

• Hazard Codes: C,T
• Statements: 22-34-61
• Safety Statements: 22-26-36/37/39-45-53
• RIDADR: UN 3259 8/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 6923-01-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
IMIDAZOLE-D4 is used as a key component in the synthesis of biologically active compounds for various pharmaceutical applications. Its presence in antifungal medications contributes to their effectiveness in treating fungal infections.
Used in Corrosion Inhibition:
IMIDAZOLE-D4 is used as a corrosion inhibitor for transition metals, such as copper, to protect them from degradation and extend their lifespan in various industrial applications.
Used in NMR Research and Analyses:
IMIDAZOLE-D4 is used as a deuterated NMR solvent, enabling researchers to conduct NMR-based studies and analyses with enhanced accuracy and precision.
Used in Synthesis of Perdeuterated Cellulose Solvents:
IMIDAZOLE-D4 is used as a reactant in the synthesis of 1-ethylimidazole-d8 and 1-butylimidazole-d12, which serve as precursors for the preparation of perdeuterated cellulose solvents, such as 1-ethyl-3-methylimidazolium acetate (EMIM-OAc-d14) and 1-butyl-3-methylimidazolium acetate (BMIM-OAc-d18). These solvents have potential applications in various chemical and industrial processes.

InChI:InChI=1/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)/i1D,2D,3D/hD

Upstream product

• 288-32-4 1H-imidazole 

Downstream Products

• 53716-58-8 4,5-dideuterio-1H-imidazole 
• 6745-43-3 (2,4,5-d3)imidazole 
• 887647-60-1 [(5,10,15,20-tetraphenylchlorin^(2-))Fe(imidazole-d4)2]Cl 

Relevant articles and documents

METHOD FOR PRODUCING COMPOUND HAVING DEUTERATED AROMATIC RING OR HETEROCYCLIC RING

A method for producing a compound having a deuterated aromatic ring or heterocyclic ring according to the invention includes heating a compound having an aromatic ring or heterocyclic ring in the presence of heavy water, a transition metal and a metal which generates deuterium. As the metal which generates deuterium, at least one metal selected from the group consisting of aluminum, magnesium, zinc, iron, lead and tin is preferred. As the transition metal, at least one metal selected from the group consisting of platinum, palladium, ruthenium and rhodium is preferred. The heating is preferably carried out by microwave irradiation.

Strong coupling effects in the polarized IR spectra of the chain hydrogen bond systems in imidazole crystals: H/D isotopic 'self-organization' effects in the IR spectra of isotopically diluted imidazole single crystals

This paper presents the investigation results of the polarized IR spectra of H1245 imidazole crystals and of D1H245, D1245 and H1D245 imidazole deuterium derivative crystals. The spectra were measured using polarized light at the room temperature and at 77 K by a transmission method, for two different crystalline faces. Theoretical analysis of the results concerned linear dichroic effects, H/D isotopic and temperature effects, observed in the spectra of the hydrogen and of the deuterium bonds in imidazole crystals, at the frequency ranges of νN-H and νN-D bands. The basic crystal spectral properties can be satisfactorily interpreted in a quantitative way for a hydrogen bond linear dimer model. Such a model explains not only a two-branch structure of the νN-H and νN-D bands in crystalline spectra, but also some essential linear dichroic effects in the band frequency ranges, for isotopically diluted crystals. Model calculations, performed within the limits of the strong-coupling model, allowed for quantitative interpretation and for understanding of the basic properties of the hydrogen bond IR spectra of imidazole crystals, H/D isotopic, temperature and dichroic effects included. The results allowed verification of theoretical models proposed recently for the imidazole crystal spectra generation mechanisms. In the scope of our studies, the mechanism of H/D isotopic self-organization processes, taking place in the crystal hydrogen bond lattices, was also recognized. It was proved that for isotopically diluted crystalline samples of imidazole, a non-random distribution of protons and deuterons exclusively occurs in some restricted fragments (domains) of open chains of the hydrogen-bonded molecules. Nevertheless, these co-operative interactions between the hydrogen bonds do not concern adjacent fragments of neighboring hydrogen bond chains in the lattice. Analysis of the isotopic self-organization effects in the spectra of imidazole crystals delivered crucial arguments for understanding of the nature of the hydrogen bond spectra generation mechanisms.

A highly efficient synthetic procedure for deuteriating imidazoles and imidazolium salts

Both substituted imidazoles and 1,3-dialkylimidazolium salts can be fully deuteriated on the heterocyclic ring using D2O over heterogeneous Pd catalysts: deuteriated 1-alkyl-3-methylimidazolium chloride and hexafluorophosphate ionic liquids can also be prepared in good yields utilising readily available and relatively low cost sources of deuterium.

Vibrational analysis of the imidazolate ring

IR and Raman spectra have been investigated for imidazolate and 4-methylimidazolate including five and three deuterated analogs, respectively.Assignment of the observed IR and Raman bands has been made on the basis of isotopic frequency shifts, Raman polarization properties, and normal coordinate calculations.The calculated normal frequencies are in good agreement with experimental ones: the average error below 1600 cm-1 is 4.5 cm-1 for 104 in-plane vibrations and 3.8 cm-1 for 43 out-of-plane vibrations.The calculated vibrational modes are useful in analyzing thc Raman bands of histidine residues in proteins.