18637-83-7

Basic information

• Product Name: 1,1'-OXALYLDIIMIDAZOLE
• Synonyms: 1,1'-Oxalyldi(1H-imidazole);1,2-Bis(1H-imidazole-1-yl)-1,2-ethanedione;1,2-Bis(1H-imidazole-1-yl)ethane-1,2-dione;1,2-Bis(1H-imidazole-1-yl)ethanedione;1,2-Bis(1-imidazolyl)ethane-1,2-dione;1H-Imidazole, 1,1'-(1,2-dioxo-1,2-ethanediyl)bis-;1,1'-OxalyldiiMidazole, technical;1,2-di(1H-iMidazol-1-yl)ethane-1,2-dione
• CAS NO: 18637-83-7
• Molecular Formula: C₈H₆N₄O₂
• Molecular Weight: 190.16
• Product Categories: Peptide Synthesis;Biochemistry;Condensation & Active Esterification;Coupling Reactions (Peptide Synthesis);Peptide Synthesis;Synthetic Organic Chemistry;Carbonyldiimidazole DerivativesSynthetic Reagents;Coupling;Others
• Mol File: 18637-83-7.mol

Chemical Properties

• Melting Point: 114-116 °C(lit.)
• Boiling Point: 441.4°Cat760mmHg
• Flash Point: 220.7°C
• Appearance: Yellow to brown/Powder
• Density: 1.46g/cm³
• Storage Temp.: Refrigerator
• PKA: 1.92±0.10(Predicted)
• BRN: 611833
• CAS DataBase Reference: 1,1'-OXALYLDIIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-OXALYLDIIMIDAZOLE(18637-83-7)
• EPA Substance Registry System: 1,1'-OXALYLDIIMIDAZOLE(18637-83-7)

Safety Data

• Hazard Codes: C
• Statements: 21/22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3259 8/PG 3
• WGK Germany: 3
• F: 8-10-21
• Hazardous Substances Data: 18637-83-7(Hazardous Substances Data)

Usage

Uses

Used in Coordination Chemistry:
1,1'-OXALYLDIIMIDAZOLE is used as a ligand for forming stable complexes with metal ions, which is crucial in the study and application of coordination chemistry. Its ability to chelate metal ions enhances the stability and reactivity of metal complexes, facilitating various chemical reactions.
Used in Synthetic Organic Chemistry:
As a reagent in synthetic organic chemistry, 1,1'-OXALYLDIIMIDAZOLE aids in the synthesis of complex organic molecules. Its unique structure and metal-chelating properties make it a valuable component in the development of new synthetic pathways and methodologies.
Used in Catalysis:
1,1'-OXALYLDIIMIDAZOLE is employed as a catalyst or a catalyst precursor in various chemical reactions. Its metal-complexing ability contributes to the activation of substrates and the acceleration of reaction rates, making it a useful component in catalytic processes.
Used in Metal-Mediated Organic Synthesis:
In metal-mediated organic synthesis, 1,1'-OXALYLDIIMIDAZOLE serves as a key intermediate that facilitates the formation of desired products through metal-catalyzed reactions. Its role in these processes is essential for the synthesis of complex organic compounds that are otherwise difficult to access.
Used in Pharmaceutical Production:
1,1'-OXALYLDIIMIDAZOLE is utilized in the production of pharmaceuticals, where its metal-chelating and synthetic properties are harnessed to create novel drug candidates with potential therapeutic applications.
Used in Agrochemical Production:
In the agrochemical industry, 1,1'-OXALYLDIIMIDAZOLE is applied in the synthesis of compounds with pesticidal or herbicidal properties, leveraging its chemical reactivity and metal-complexing characteristics to develop effective crop protection agents.
Used in Specialty Chemicals Production:
1,1'-OXALYLDIIMIDAZOLE is also used in the production of specialty chemicals, where its unique attributes are exploited to create high-value products for specific applications in various industries.
Used in Antimicrobial and Antifungual Applications:
1,1'-OXALYLDIIMIDAZOLE is used as an antimicrobial and antifungal agent in industrial and agricultural applications. Its properties help control the growth of harmful microorganisms, contributing to the preservation of materials and the protection of crops from diseases.

Upstream product

• 71638-08-9 1-(diphenylphosphinoyl)imidazole 
• 288-32-4 1H-imidazole 
• 1165-91-9 bis(2,4,6-trichlorophenyl) oxalate 
• 16536-30-4 bis(2,4-dinitrophenyl) oxalate 
• 79-37-8 oxalyl dichloride 
• 18156-74-6 1-(Trimethylsilyl)imidazole 
• 66778-06-1 diphenyl (1H-imidazol-1-yl)phosphonate 

Downstream Products

• 10347-11-2 4-(methylbenzoyl)imidazoline 
• 3197-61-3 N-formylimidazole 

Relevant articles and documents

Preparation of N'-[2-(5,6-dimethylbenzothiazolyl)]-N-furfuryloxamide with plant growth regulatory activity

The reaction of the N-furfuryloxamic acid sodium salt (12) with 1,1'-oxalyldiimidazole (ODI) yielded the imidazolide (13) as an intermediate, and this directly reacted with 2-aminothiazole derivatives (14) or 2-aminobenzothiazole derivatives (15) under es

Kinetics and mechanism of the nucleophilic substitution reaction of imidazole with bis(2,4,6-trichlorophenyl) oxalate and bis(2,4-dinitrophenyl) oxalate

The kinetics of the imidazole-catalyzed decomposition of bis(2,4,6-trichlorophenyl) oxalate (TCPO) and bis(2,4-dinitrophenyl) oxalate (DNPO) was investigated by the stopped-flow technique. Pseudo-first-order rate constants were determined as a function imidazole concentration in the temperature range 6-45 °C by fitting the temporal changes in absorbance throughout the 245 to 345 nm wavelength range for TCPO and at 420 nm for DNPO. The reaction proceeds by release of two molecules of substituted phenol and formation of 1,1′-oxalyldiimidazole (ODI) for both esters. The identity of ODI was confirmed in the reaction of imidazole with TCPO by its UV absorbance spectrum and 13C-NMR spectrum. The reaction of imidazole with TCPO has a second-order dependence on imidazole concentration and an observed negative activation energy of -6.2 ± 0.3 kJ/mol, whereas the DNPO reaction has a first-order dependence on imidazole concentration and an observed positive activation energy of 12.0 ± 0.6 kJ/mol. The differences in the temperature dependence and order of the reaction with respect to imidazole for the two oxalate esters are explained by a shift in the rate-determining step from addition to the acyl group for DNPO to imidazole-catalyzed release of the phenol leaving group for TCPO. These kinetics results are useful in interpreting the initial reaction steps in peroxyoxalate chemiluminescence.

Stopped-Flow Kinetics Investigation of the Imidazole-Catalyzed Peroxyoxalate Chemiluminescence Reaction

The stopped-flow technique was used to study the temperature-dependent kinetics of the imidazole- catalyzed peroxyoxalate reaction in order to further elucidate the reaction mechanism. Pseudo- first-order rate constants were obtained from the chemiluminescence intensity vs time profiles for the sequential reaction model X → Y → Z over a wide range of initial concentrations of each of the following reagents: bis(2,4,6-trichlorophenyl) oxalate (TCPO), imidazole (ImH), and hydrogen peroxide. These measurements were complemented by UV absorbance measurements of the kinetics of the step X → Y. For both reaction conditions pseudo-flrst-order in TCPO ([ImH], [H2O2] [TCPO]) and pseudo-first-order in H2O2 ([ImH][TCPO][H2O2]), the first step of the reaction is nucleophilic substitution by two imidazole molecules to form 1,1′-oxalyldiimidazole (ODI). Under conditions of excess TCPO in the concentration range 0.075-0.25 mM, the Y → Z reaction probed the subsequent reaction of ODI with H2O2 to form the imidazoyl peracid intermediate, ImC(O)C(O)OOH, For excess H2O2 concentrations in the range 2.5-15 mM, the reaction of H2O2 with ODI is fast, and the Y → Z step of the sequential reaction model describes subsequent reactions of the imidazoyl peracid. An important unexpected finding necessary for interpreting the kinetics of this reaction is that under conditions of a large excess of H2O2 the faster rise of the chemiluminescence signal corresponds to the second step of the reaction (Y → Z), and the slower fall of the signal corresponds to the first step (X → Y). Lutidine and collidine, amine bases of similar aqueous pKa as imidazole, displayed very little catalytic effect on the PO-CL reaction in comparison to imidazole, corroborating the conclusion that nucleophilic catalysis with formation of ODI as an intermediate constitutes the principal reaction pathway under conditions of both excess oxalate ester and excess H2O2. Imidazole quenches the quantum yield of the reaction, a result that can be well explained by catalysis of the decomposition of the key energy-transfer intermediate.

Study of the characteristics of three high-energy intermediates generated in peroxyoxalate chemiluminescence (PO-CL) reactions

Perylene emission intensity generated from peroxyoxalate chemiluminescence (PO-CL) reactions was studied as a function of time and order of reagent addition. Based on 1H-NMR analyses, kinetics of UV absorbance and emission intensity vs. time profiles, we

Preparation and plant growth-regulatory activity of N'-substituted N- furfuryloxamides

N'-Substituted N-furfuryloxamides (4) were prepared via condensation of potassium methyl oxalate (8) with furfurylamine (5f) using 1,1'- oxalyldiimidazole (6), followed by hydrolysis of the resulting amide-ester (10), and finally condensation with aliphatic or aromatic amines (5). The prepared compounds (4) were examined for activity as plant growth regulators using two kinds of plant seeds, namely, those of rape, Brassica campestris L. (Dicotyledoneae) and leek, Allium tuberosum ROTTLER (Monocotyledoneae). N'- Benzyl- and N'-phenyl-N-furfuryloxamides (4b and 4c) and N,N'- difurfuryloxamide (4f) inhibited root growth in seedlings of both species.

Kinetic studies on the peroxyoxalate chemiluminescent reaction: imidazole as a nucleophilic catalyst

The peroxyoxalate system undergoes one of the most efficient chemiluminescence reactions and is the only one supposed to involve an intermolecular chemically induced electron exchange luminescence (CIEEL) mechanism, with proven high efficiency.In this work we report kinetic results on the reaction of bis(2,4,6-trichlorophenyl) oxalate (TCPO) with hydrogen peroxide, catalysed by imidazole (IMI), in the presence of chemiluminescence activators.The kinetics were followed by measurement of the intensity of light emission and the 2,4,6-trichlorophenol (TCP) release, observed as an absorption change.From the dependence of the observed rate constants on the concentrations of TCPO, imidazole, hydrogen peroxide and activator, we attribute rate constants to three elementary steps in the proposed simplified mechanistic scheme.The initial step consists of attack of the nucleophilic imidazole on TCPO.A bimolecular (k1(2) = 1.4 +/- 0.1 dm3 mol-1 s-1) and a trimolecular 1(3) = (9.78 +/- 0.08) 102 dm6 mol-2 s-1> rate constant can be attributed to this step.The imidazolide subsequently suffers imidazole-catalysed peroxide attack, leading to a peracid derivative; trimolecular rate constants k2(3) = (1.86 +/- 0.06) 104 dm6 mol-2 s-1 and k2(3)' = (8.7 +/- 0.2) 103 dm6mol-2s-1 can be obtained for this step from the peroxide and the imidazole dependence, respectively.The cyclization of the peracid affords the reactive intermediate, which we believe to be 1,2-dioxetanedione; a rough estimate of k3 ca. 0.2 s-1 (at = 1.0 mmol dm3) is obtained for this step.Finally, the interaction of the activator with the reactive intermediate, probably involving the CIEEL sequence and leading ultimately to light emission, is extremely fast and cannot be observed kinetically.

Neutral hydrolysis and imidazole-catalysed decomposition of bis(4-nitrophenyl) oxalate. 1,1'-Oxalyldiimidazole as an intermediate

Neutral hydrolysis and imidazole-catalysed decomposition of a peroxyoxalate chemiluminescence reagent type compound, bis(4-nitrophenyl) oxalate (4-NPO), have been studied in acetonitrile and in acetonitrile-water mixtures.For comparison, the rate coeffici

An experimental estimation of aromaticity relative to that of benzene. The synthesis and NMR properties of a series of highly annelated dimethyldihydropyrenes: Bridged benzannulenes

The synthesis of 13 trans-dimethyldihydropyrenes (bridged [14]annulenes) fused to one or more benzene, naphthalene, phenanthrene, phenalene, or quinoxaline rings and 6 cis-dihydropyrene derivatives from benzenoid precursors using either a thiacyclophane route or an electrocyclic addition of a furan to an annulyne followed by deoxygenation is reported. Their 1H NMR spectra are studied in detail to obtain correlations between 3JH,H coupling constants and the internal methyl proton chemical shifts and also between the latter and the more distant external annulene ring proton shifts. These linear correlations are then used to obtain a relationship between the relative aromaticity of benzene and the fused ring in question, such that the aromaticity of the fused ring can be estimated relative to that of a benzene ring simply from a measurement of chemical shift in the fused annulene.

New General Synthesis of Organophosphorus P-F Compounds via Reaction of Azolides of Phosphorus Acids with Acyl Fluorides: Novel Route to 2-Deoxynucleosidyl Phosphorofluoridates and Phosphorodifluoridates

Tetra- and tri-coordinate P-N-imidazole derivatives and their structural analogous react smoothly with acyl fluorides to give the corresponding P-F compounds an almost quantitative yield.This method has been successfully applied to produce 2-deoxynucleosidyl phosphorofluoridates and phosphorodifluoridates.