PRODUCTS

IMIDAZOLE

Imidazole (ImH) is an organic compound with the formula C3N2H4.
Imidazole is a white or colourless solid that is soluble in water, producing a mildly alkaline solution.
In chemistry, Imidazole is an aromatic heterocycle, classified as a diazole, and has non-adjacent nitrogen atoms in meta-substitution.

CAS Number: 288-32-4
EC Number: 206-019-2
Chemical Formula: C3H4N2
Molar Mass: 68.077 g/mol

Imidazole is a five-membered heterocycle that is found in many naturally occurring compounds.
Imidazole exhibits both acidic and basic properties.

Imidazole is reported to be an inhibitor of thromboxane formation.
Imidazole vertical spectrum and the radiationless decay have been recorded and analyzed.

Imidazole is useful as a buffer in the pH range of 6.2-7.8 One of the applications of imidazole is in the purification of His-tagged proteins in immobilised metal affinity chromatography(IMAC).
Imidazole is used to elute tagged proteins bound to Ni ions attached to the surface of beads in the chromatography column.

An excess of imidazole is passed through the column, which displaces the His-tag from nickel co-ordination, freeing the His-tagged proteins.
Imidazole has become an important part of many pharmaceuticals.

Synthetic imidazoles are present in many fungicides and antifungal, antiprotozoal, and antihypertensive medications.
Imidazole is part of the theophylline molecule, found in tea leaves and coffee beans, which stimulates the central nervous system.
Imidazole is present in the anticancer medication mercaptopurine, which combats leukemia by interfering with DNA activities.

Imidazole is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 tonnes per annum.
Imidazole is used by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

Many natural products, especially alkaloids, contain the imidazole ring.
These imidazoles share the 1,3-C3N2 ring but feature varied substituents.

This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.
Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.

When fused to a pyrimidine ring, Imidazole forms a purine, which is the most widely occurring nitrogen-containing heterocycle in nature.
The name "imidazole" was coined in 1887 by the German chemist Arthur Rudolf Hantzsch (1857–1935).

Imidazole, any of a class of organic compounds of the heterocyclic series characterized by a ring structure composed of three carbon atoms and two nitrogen atoms at nonadjacent positions.
The simplest member of the imidazole family is imidazole itself, a compound with molecular formula C3H4N2.

Imidazole was first prepared in 1858.
Other imidazole compounds have been known longer: allantoin (discovered in 1800) and parabanic acid were prepared in 1837 from uric acid.
The amino acid histidine and Imidazole decomposition product histamine have the imidazole structure, as does biotin, a growth factor for both humans and yeast.

Imidazoles, benzimidazoles, imidazolines, imidazolidines, and related carbenes are classes of heterocyclic compounds possessing unique chemical and physical properties.
Tremendous advances in imidazole chemistry have been made in the decade since 1995, and are manifested in the large body of the literature related to imidazole and Imidazole analogs.

This chapter reviews important developments in imidazole chemistry from 1996 to 2006.
Major portions of the chapter are devoted to the reactivity and synthesis of imidazole and Imidazoles analogs.

Special attention has been given to the transformations involving transition metal catalysts and N-heterocyclic carbenes.
Theoretical, experimental, structural and thermodynamic studies, and the applications of imidazole and Imidazole analogs are also covered.

Imidazole (ImH) is an organic compound with the formula C3N2H4.
Imidazole is a white or colourless solid that is soluble in water, producing a mildly alkaline solution.

In chemistry, Imidazole is an aromatic heterocycle, classified as a diazole, and has non-adjacent nitrogen atoms in meta-substitution.
Many natural products, especially alkaloids, contain the imidazole ring.

These imidazoles share the 1,3-C3N2 ring but feature varied substituents.
This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.

Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.
When fused to a pyrimidine ring, Imidazole forms a purine, which is the most widely occurring nitrogen-containing heterocycle in nature.
The name "imidazole" was coined in 1887 by the German chemist Arthur Rudolf Hantzsch (1857–1935).

Imidazoles have occupied a unique position in heterocyclic chemistry, and Imidazole derivatives have attracted considerable interests in recent years for their versatile properties in chemistry and pharmacology.
Imidazole is nitrogen-containing heterocyclic ring which possesses biological and pharmaceutical importance.

Thus, imidazole compounds have been an interesting source for researchers for more than a century.
The imidazole ring is a constituent of several important natural products, including purine, histamine, histidine, and nucleic acid.

Being a polar and ionisable aromatic compound, Imidazole improves pharmacokinetic characteristics of lead molecules and thus is used as a remedy to optimize solubility and bioavailability parameters of proposed poorly soluble lead molecules.
There are several methods used for the synthesis of imidazole-containing compounds, and also their various structure reactions offer enormous scope in the field of medicinal chemistry.

The imidazole derivatives possess extensive spectrum of biological activities such as antibacterial, anticancer, antitubercular, antifungal, analgesic, and anti-HIV activities.
Imidazole nucleus forms the main structure of some well-known components of human organisms, that is, the amino acid histidine, Vit-B12, a component of DNA base structure and purines, histamine, and biotin.

Imidazole is also present in the structure of many natural or synthetic drug molecules, that is, cimetidine, azomycin, and metronidazole.
Imidazole-containing drugs have a broaden scope in remedying various dispositions in clinical medicine.

Imidazole was first synthesized by Heinrich Debus in 1858, but various imidazole derivatives had been discovered as early as the 1840s.
His synthesis used glyoxal and formaldehyde in ammonia to form imidazole.
This synthesis, while producing relatively low yields, is still used for creating C-substituted imidazoles.

Imidazole is a 5-membered planar ring, which is soluble in water and other polar solvents.
Imidazole exists in two equivalent tautomeric forms because the hydrogen atom can be located on either of the two nitrogen atoms.

Imidazole is a highly polar compound, as evidenced by a calculated dipole of 3.61D, and is entirely soluble in water.
Imidazole is amphoteric; that is, Imidazole can function as both an acid and a base.
Imidazole is classified as aromatic due to the presence of a sextet of π-electrons, consisting of a pair of electrons from the protonated nitrogen atom and one from each of the remaining four atoms of the ring.

Salts of Imidazole:
Salts of imidazole where the imidazole ring is the cation are known as imidazolium salts (for example, imidazolium chloride or nitrate).
These salts are formed from the protonation or substitution at nitrogen of imidazole.

These salts have been used as ionic liquids and precursors to stable carbenes.
Salts where a deprotonated imidazole is an anion are also well known; these salts are known as imidazolates (for example, sodium imidazolate, NaC3H3N2).

Biological Significance and Applications:
Imidazole is incorporated into many important biological compounds.
The most pervasive is the amino acid histidine, which has an imidazole side-chain.
Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.

Imidazole-based histidine compounds play a very important role in intracellular buffering.
Histidine can be decarboxylated to histamine.
Histamine can cause urticaria (hives) when Imidazole is produced during allergic reaction.

Imidazole substituents are found in many pharmaceuticals.
Synthetic imidazoles are present in many fungicides and antifungal, antiprotozoal, and antihypertensive medications.

Imidazole is part of the theophylline molecule, found in tea leaves and coffee beans, that stimulates the central nervous system.
Imidazole is present in the anticancer medication mercaptopurine, which combats leukemia by interfering with DNA activities.

A number of substituted imidazoles, including clotrimazole, are selective inhibitors of nitric oxide synthase, which makes them interesting drug targets in inflammation, neurodegenerative diseases and tumors of the nervous system.
Other biological activities of the imidazole pharmacophore relate to the downregulation of intracellular Ca2+ and K+ fluxes, and interference with translation initiation.

Pharmaceutical derivatives:
The substituted imidazole derivatives are valuable in treatment of many systemic fungal infections.
Imidazoles belong to the class of azole antifungals, which includes ketoconazole, miconazole, and clotrimazole.

For comparison, another group of azoles is the triazoles, which includes fluconazole, itraconazole, and voriconazole.
The difference between the imidazoles and the triazoles involves the mechanism of inhibition of the cytochrome P450 enzyme.

The N3 of the imidazole compound binds to the heme iron atom of ferric cytochrome P450, whereas the N4 of the triazoles bind to the heme group.
The triazoles have been shown to have a higher specificity for the cytochrome P450 than imidazoles, thereby making them more potent than the imidazoles.

Some imidazole derivatives show effects on insects, for example sulconazole nitrate exhibits a strong anti-feeding effect on the keratin-digesting Australian carpet beetle larvae Anthrenocerus australis, as does econazole nitrate with the common clothes moth Tineola bisselliella.

Applications of Imidazole:

Industrial Applications:
Imidazole itself has few direct applications.
Imidazole is instead a precursor to a variety of agrichemicals, including enilconazole, climbazole, clotrimazole, prochloraz, and bifonazole.

Uses of Imidazole:
Imidazole is used as an intermediate (pharmaceuticals, pesticides, dye intermediates, auxiliaries for textile dyeing and finishing, photographic chemicals, and corrosion inhibitors) and hardener for epoxy resins.
Imidazole is also used in process regulators, anti-freeze agents, photographic application, laboratory applications, glues/adhesives, cement fillers or sealing compounds, paints, varnishes, lacquers, consumer cleaning and washing agents, swimming pool applications, and in publishing, printing, and reproduction of recorded media.

Imidazole is Karl Fischer reagent in analytical chemistry.
Imidazole is reagent in synthetic organic chemistry.

The bulk of imidazole produced is used in the preparation of biologically active compounds.

Imidazole is used in the chemical industry as an intermediate in the production of pharmaceuticals, pesticides, dye intermediates, auxiliaries for textile dyeing and finishing, photographic chemicals and corrosion inhibitors.
Imidazole is used in cosmetics as a buffering agent

Widespread uses by professional workers:
Imidazole is used in the following products: laboratory chemicals and pH regulators and water treatment products.
Imidazole is used in the following areas: scientific research and development and health services.
Other release to the environment of Imidazole is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use resulting in inclusion into or onto a materials (e.g. binding agent in paints and coatings or adhesives).

Uses at industrial sites:
Imidazole is used in the following products: laboratory chemicals, metal surface treatment products and polymers.
Imidazole has an industrial use resulting in manufacture of another substance (use of intermediates).

Imidazole is used in the following areas: scientific research and development.
Imidazole is used for the manufacture of: chemicals.
Release to the environment of Imidazole can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates), in processing aids at industrial sites, in the production of articles and for thermoplastic manufacture.

Industrial Processes with risk of exposure:
Textiles (Fiber & Fabric Manufacturing)
Painting (Pigments, Binders, and Biocides)
Plastic Composites Manufacturing
Photographic Processing

Use in Biological Research of Imidazole:
Imidazole is a suitable buffer for pH 6.2-7.8.
Pure imidazole has essentially no absorbance at protein relevant wavelenths (280 nm), however lower purities of imidazole can give notable absorbance at 280 nm.
Imidazole can interfere with the Lowry protein assay.

Coordination Chemistry of Imidazole:
Imidazole and its derivatives have high affinity for metal cations.
One of the applications of imidazole is in the purification of His-tagged proteins in immobilised metal affinity chromatography (IMAC).

Imidazole is used to elute tagged proteins bound to nickel ions attached to the surface of beads in the chromatography column.
An excess of imidazole is passed through the column, which displaces the His-tag from nickel coordination, freeing the His-tagged proteins.

Structure and Properties of Imidazole:
Imidazole is a planar 5-membered ring, that exists in two equivalent tautomeric forms because hydrogen can be bound to one or another nitrogen atom.
Imidazole is a highly polar compound, as evidenced by Imidazole electric dipole moment of 3.67 D, and is highly soluble in water.
Imidazole is classified as aromatic due to the presence of a planar ring containing 6 π-electrons (a pair of electrons from the protonated nitrogen atom and one from each of the remaining four atoms of the ring).

Amphoterism:
Imidazole is amphoteric, which is to say that Imidazole can function both as an acid and as a base.
As an acid, the pKa of imidazole is 14.5, making Imidazole less acidic than carboxylic acids, phenols, and imides, but slightly more acidic than alcohols.

The acidic proton is the one bound to nitrogen.
Deprotonation gives the imidazolide anion, which is symmetrical.

As a base, the pKa of the conjugate acid (cited as pKBH+ to avoid confusion between the two) is approximately 7, making imidazole approximately sixty times more basic than pyridine.
The basic site is the nitrogen with the lone pair (and not bound to hydrogen).
Protonation gives the imidazolium cation, which is symmetrical.

Preparation of Imidazole:
Imidazole was first reported in 1858 by the German chemist Heinrich Debus, although various imidazole derivatives had been discovered as early as the 1840s.
Imidazole was shown that glyoxal, formaldehyde, and ammonia condense to form imidazole (glyoxaline, as Imidazole was originally named).
This synthesis, while producing relatively low yields, is still used for generating C-substituted imidazoles.

In one microwave modification, the reactants are benzil, benzaldehyde and ammonia in glacial acetic acid, forming 2,4,5-triphenylimidazole ("lophine").

Imidazole can be synthesized by numerous methods besides the Debus method.
Many of these syntheses can also be applied to different substituted imidazoles and imidazole derivatives by varying the functional groups on the reactants.

These methods are commonly categorized by which and how many bonds form to make the imidazole rings.
For example, the Debus method forms the (1,2), (3,4), and (1,5) bonds in imidazole, using each reactant as a fragment of the ring, and thus this method would be a three-bond-forming synthesis.
A small sampling of these methods is presented below.

Formation of one bond:
The (1,5) or (3,4) bond can be formed by the reaction of an imidate and an α-aminoaldehyde or α-aminoacetal.
The example below applies to imidazole when R1 = R2 = hydrogen.

Formation of two bonds:
The (1,2) and (2,3) bonds can be formed by treating a 1,2-diaminoalkane, at high temperatures, with an alcohol, aldehyde, or carboxylic acid.
A dehydrogenating catalyst, such as platinum on alumina, is required.

The (1,2) and (3,4) bonds can also be formed from N-substituted α-aminoketones and formamide with heat.
Imidazole will be a 1,4-disubstituted imidazole, but here since R1 = R2 = hydrogen, imidazole itself is Imidazole.
The yield of this reaction is moderate, but Imidazole seems to be the most effective method of making the 1,4 substitution.

Formation of four bonds:
This is a general method that is able to give good yields for substituted imidazoles.
In essence, Imidazole is an adaptation of the Debus method called the Debus-Radziszewski imidazole synthesis.
The starting materials are substituted glyoxal, aldehyde, amine, and ammonia or an ammonium salt.

Formation from other heterocycles:
Imidazole can be synthesized by the photolysis of 1-vinyltetrazole.
This reaction will give substantial yields only if the 1-vinyltetrazole is made efficiently from an organotin compound, such as 2-tributylstannyltetrazole.
The reaction, shown below, produces imidazole when R1 = R2 = R3 = hydrogen.

Imidazole can also be formed in a vapor-phase reaction.
The reaction occurs with formamide, ethylenediamine, and hydrogen over platinum on alumina, and Imidazole must take place between 340 and 480 °C.
This forms a very pure imidazole product.

Van Leusen reaction:
The Van Leusen reaction can also be employed to form imidazoles starting from TosMIC and an aldimine.
The Van Leusen Imidazole Synthesis allows the preparation of imidazoles from aldimines by reaction with tosylmethyl isocyanide (TosMIC).
The reaction has later been expanded to a two-step synthesis in which the aldimine is generated in situ: the Van Leusen Three-Component Reaction (vL-3CR).

Manufacturing Methods of Imidazole:
In the generally applicable Radziszewski reaction, a 1,2-dicarbonyl compound is condensed with an aldehyde and ammonia in a molar ratio of 1:1: 2, respectively.
Replacement of a molar equivalent of ammonia with a primary amine leads to the corresponding 1-substituted imidazoles.

The reaction is usually carried out in water or a water-alcohol mixture at 50-100 °C.
Work-up may involve the usual processes (e.g., distillation, extraction, and crystallization).

Distillation leads to imidazole with a purity > 99%.
The yield is generally 60-85%.

General Manufacturing Information of Imidazole:

Industry Processing Sectors:
All Other Basic Organic Chemical Manufacturing
Plastics Material and Resin Manufacturing

Human Metabolite Information of Imidazole:

Tissue Locations:
Adrenal Cortex
Adrenal Gland
Epidermis
Liver
Neuron
Placenta
Platelet
Testis

Cellular Locations:
Cytoplasm

Handling and Storage of Imidazole:

Safe Storage:
Separated from strong acids and food and feedstuffs.

Storage Conditions:
Keep container tightly closed in a dry and well-ventilated place.
Storage class (TRGS 510): 6.1D: Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects.

Safety of Imidazole:
Imidazole has low acute toxicity as indicated by the LD50 of 970 mg/kg (Rat, oral).

Accidental Release Measures of Imidazole:

Personal protection:
Use complete protective clothing including self-contained breathing apparatus.
Sweep spilled substance into covered containers.
Then wash away with plenty of water.

Cleanup Methods of Imidazole:

Personal precautions, protective equipment and emergency procedures:
Use personal protective equipment.
Avoid dust formation.

Avoid breathing vapors, mist or gas.
Ensure adequate ventilation.

Evacuate personnel to safe areas.
Avoid breathing dust.

Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.

Methods and materials for containment and cleaning up:
Pick up and arrange disposal without creating dust.
Sweep up and shovel.
Keep in suitable, closed containers for disposal.

Personal protection:
Use complete protective clothing including self-contained breathing apparatus.
Sweep spilled substance into covered containers.
Then wash away with plenty of water.

Disposal Methods of Imidazole:
Recycle any unused portion of the material for Imidazole approved use or return it to the manufacturer or supplier.

Ultimate disposal of the chemical must consider:
Imidazole's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations.
If Imidazole is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Contact a licensed professional waste disposal service to dispose of Imidazole.
Dissolve or mix Imidazole with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Offer surplus and non-recyclable solutions to a licensed disposal company;

Contaminated packaging:
Dispose of as unused product.

Identifiers of Imidazole:
CAS Number: 288-32-4
ChEBI: CHEBI:16069
ChEMBL: ChEMBL540
ChemSpider: 773
ECHA InfoCard: 100.005.473
EC Number: 206-019-2
KEGG: C01589
PubChem CID: 795
RTECS number: NI3325000
UNII: 7GBN705NH1
CompTox Dashboard (EPA): DTXSID2029616
InChI: InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
Key: RAXXELZNTBOGNW-UHFFFAOYSA-N
InChI=1/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
Key: RAXXELZNTBOGNW-UHFFFAOYAS
SMILES: c1cnc[nH]1

Synonym(s): 1,3-Diaza-2,4-cyclopentadiene, Glyoxaline
Empirical Formula (Hill Notation): C3H4N2
CAS Number: 288-32-4
Molecular Weight: 68.08
Beilstein: 103853
EC Number: 206-019-2
MDL number: MFCD00005183
eCl@ss: 39161001
PubChem Substance ID: 24895975
NACRES: NA.21

EC / List no.: 206-019-2
CAS no.: 288-32-4
Mol. formula: C3H4N2

CAS number: 288-32-4
EC index number: 613-319-00-0
EC number: 206-019-2
Hill Formula: C₃H₄N₂
Molar Mass: 68.08 g/mol
HS Code: 2933 29 90

Properties of Imidazole:
Chemical formula: C3H4N2
Molar mass: 68.077 g/mol
Appearance: White or pale yellow solid
Density: 1.23 g/cm3, solid
Melting point: 89 to 91 °C (192 to 196 °F; 362 to 364 K)
Boiling point: 256 °C (493 °F; 529 K)
Solubility in water: 633 g/L
Acidity (pKa): 6.95 (for the conjugate acid)
UV-vis (λmax): 206 nm

Grade: ACS reagent
Quality Level: 200
Vapor pressure: <1 mmHg ( 20 °C)
Assay: ≥99% (titration)
Impurities: ≤0.2% water
Ign. residue: ≤0.1%
pH: 9.5-11.0 (25 °C, 5% in H2O)
pKa (25 °C): 6.95
bp: 256 °C (lit.)
mp: 88-91 °C (lit.)
Cation traces: Fe: ≤0.001%
SMILES string: c1c[nH]cn1
InChI: 1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
InChI key: RAXXELZNTBOGNW-UHFFFAOYSA-N

Boiling point: 256 °C (1013 hPa)
Density: 1.233 g/cm3 (20 °C)
Flash point: 145 °C
Ignition temperature: 480 °C
Melting Point: 90.5 °C
pH value: 10.5 (67 g/l, H₂O, 20 °C)
Vapor pressure: 0.003 hPa (20 °C)
Bulk density: 500 - 600 kg/m3
Solubility: 633 g/l

Molecular Weight: 68.08
XLogP3: -0.1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 0
Exact Mass: 68.037448136
Monoisotopic Mass: 68.037448136
Topological Polar Surface Area: 28.7 Å²
Heavy Atom Count: 5
Complexity: 28.1
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of Imidazole:
Assay (GC, area%): ≥ 99.0 % (a/a)
Melting range (lower value): ≥ 88 °C
Melting range (upper value): ≤ 91 °C
Water (K. F.): ≤ 0.20 %
Identity (IR): passes test

Structure of Imidazole:
Crystal structure: Monoclinic
Coordination geometry: Planar 5-membered ring
Dipole moment: 3.61 D

Related heterocycles:
Benzimidazole, an analog with a fused benzene ring
Dihydroimidazole or imidazoline, an analog where the 4,5-double bond is saturated
Pyrrole, an analog with only one nitrogen atom in position 1
Oxazole, an analog with the nitrogen atom in position 1 replaced by oxygen
Thiazole, an analog with the nitrogen atom in position 1 replaced by sulfur
Pyrazole, an analog with two adjacent nitrogen atoms
Triazoles, analogs with three nitrogen atoms

Names of Imidazole:

Regulatory process names:
1,3-Diaza-2,4-cyclopentadiene
1,3-Diazole
Formamidine, N,N'-vinylene-
Glioksal
Glyoxalin
Glyoxaline
IMD
Imidazol
Imidazole
Iminazole
Imutex
Methanimidamide, N,N'-1,2-ethenediyl-
Miazole
Pyrro(b)monazole

Translated names:
imidasool (et)
Imidatsoli (fi)
imidazol (cs)
imidazol (da)
Imidazol (de)
imidazol (es)
imidazol (hr)
imidazol (hu)
imidazol (pl)
imidazol (ro)
imidazol (sk)
imidazol (sl)
imidazol (sv)
imidazolas (lt)
imidazole (fr)
imidazole (pt)
imidazolo (it)
imidazols (lv)
Imidazool (nl)
imidażol (mt)
ιμιδαζόλιο (el)
имидазол (bg)

CAS names
1H-Imidazole

IUPAC names
(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid
1, 3-diaea-2, 4-cyclopentadiene
1,3- diazole Imidazole
1,3-diaza-2,4-ciclopentadieno
1,3-Diaza-2,4-cyclopentadien
1,3-diaza-2,4-cyclopentadiene
1,3-Diaza-2,4-cyclopentadiene, Glyoxaline
1-H-Imidazole
1H-IMIDAZOLE
1H-Imidazole
1H-imidazole
1H-imidazole
Imidazol
Imidazol
IMIDAZOLE
Imidazole
imidazole
IMIDAZOLE
Imidazole
imidazole

Preferred IUPAC name:
1H-Imidazole

Systematic IUPAC name:
1,3-Diazacyclopenta-2,4-diene

Trade names:
Imidazole

Other names:
1,3-Diazole
Glyoxaline (archaic)

Other identifiers:
116421-26-2
116421-26-2
146117-15-9
146117-15-9
288-32-4

Synonyms of Imidazole:
imidazole
1H-Imidazole
288-32-4
Glyoxaline
Imidazol
Iminazole
Miazole
1,3-Diazole
Glyoxalin
Imutex
1,3-Diaza-2,4-cyclopentadiene
Pyrro(b)monazole
USAF EK-4733
Pyrro[b]monazole
Formamidine, N,N'-vinylene-
Glioksal [Polish]
Glioksal
Methanimidamide, N,N'-1,2-ethenediyl-
IMD
CCRIS 3345
AI3-24703
NSC 60522
BRN 0103853
1H-Imidazole, dimer
DTXSID2029616
N,N'-vinyleneformamidine
CHEMBL540
7GBN705NH1
CHEBI:16069
N,N'-1,2-ethenediylmethanimidamide
MFCD00005183
NSC-60522
227760-40-9
DTXCID809616
1H-imidazol
CAS-288-32-4
Imidazole (8CI)
NSC51860
Imidazole, puriss. p.a., >=99.5% (GC)
EINECS 206-019-2
NSC 51860
UNII-7GBN705NH1
Immidazole
imidazole-
1-H-imidazole
Glyoxaline solution
Imidazole, Reagent
{Pyrro[b]monazole}
1,4-cyclopentadiene
Imidazole, ACS grade
1H-Imidazole (9CI)
IMIDAZOLE [MI]
IMIDAZOLE [INCI]
Imidazole buffer Solution
Formamidine,N'-vinylene-
bmse000096
bmse000790
WLN: T5M CNJ
EC 206-019-2
ENALAPRIL IMPURITY I
IMIDAZOLE [USP-RS]
IMIDAZOLE [WHO-DD]
NCIStruc1_001975
NCIStruc2_000693
Imidazole, LR, >=99%
5-23-04-00191 (Beilstein Handbook Reference)
MLS001055465
BDBM7882
Imidazole-buffered saline (5X)
Imidazole-[2-13C,15N2]
HSDB 8449
1,3-Diaza-2,4-cyclopentadiene-
Imidazole, ReagentPlus(R), 99%
ZINC901039
Imidazole, for synthesis, 99.5%
BCP26547
HY-D0837
NSC60522
Methanimidamide,N'-1,2-ethenediyl-
Tox21_201504
Tox21_303345
s6006
STK362967
AKOS000120177
AM82000
CS-5135
DB03366
Imidazole, BioUltra, >=99.5% (GC)
NCGC00090984-01
NCGC00090984-02
NCGC00257344-01
NCGC00259055-01
2,4-Diazonia-2,4-cyclopentadiene-1-ide
BP-11451
Him
SMR000057825
1,3-Diaza-2,4-cyclopentadiene;Glyoxaline
Imidazole, SAJ special grade, >=99.0%
Imidazole, Vetec(TM) reagent grade, 98%
DB-002018
CLOTRIMAZOLE IMPURITY D [EP IMPURITY]
FT-0627179
FT-0670295
I0001
I0014
I0288
I0290
Imidazole, >=99% (titration), crystalline
EN300-19083
Imidazole Zone Refined (number of passes:30)
Imidazole, ACS reagent, >=99% (titration)
C01589
P17516
ENALAPRIL MALEATE IMPURITY I [EP IMPURITY]
Q328692
J-200340
SILDENAFIL CITRATE IMPURITY E [EP IMPURITY]
Imidazole, for molecular biology, >=99% (titration)
F2190-0638
Z104472692
Imidazole, BioUltra, for molecular biology, >=99.5% (GC)
Imidazole, European Pharmacopoeia (EP) Reference Standard
4286D518-643C-4C69-BCE7-519D073F4992
Imidazole, pharmaceutical impurity standard, >=95.0% (HPLC)
Imidazole, United States Pharmacopeia (USP) Reference Standard
Imidazole;1,3-diazole; glyoxaline; 1,3-diazacyclopenta-2,4-diene
ONDANSETRON HYDROCHLORIDE DIHYDRATE IMPURITY E [EP IMPURITY]
ONDANSETRON HYDROCHLORIDE IMPURITY, IMIDAZOLE- [USP IMPURITY]
Imidazole, anhydrous, free-flowing, Redi-Dri(TM), ACS reagent, >=99%
Imidazole, Pharmaceutical Secondary Standard; Certified Reference Material
Ondansetron impurity E, European Pharmacopoeia (EP) Reference Standard
1,3-Diaza-2,4-cyclopentadiene
103853 [Beilstein]
1H-Imidazol [German] [ACD/IUPAC Name]
1H-Imidazole [ACD/Index Name] [ACD/IUPAC Name]
1H-Imidazole [French] [ACD/Index Name] [ACD/IUPAC Name]
206-019-2 [EINECS]
288-32-4 [RN]
36364-49-5 [RN]
Glyoxaline
imidazol
Imidazole [Wiki]
MFCD00005183 [MDL number]
mono-imidazole
1,3-Diazacyclopenta-2,4-diene
1,3-Diazole
116421-26-2 secondary RN [RN]
146117-15-9 secondary RN [RN]
5-23-04-00191 [Beilstein]
5-dihydro-1H-imidazole
6745-43-3 [RN]
6923-01-9 [RN]
Formamidine, N,N'-vinylene-
Glyoxalin
Glyoxaline, 1
Glyoxaline, Iminazole
IMD
Imidazole buffermissing
Imidazole-buffered saline (5X)
imidazole-d3
Imidazolemissing
iminazole
Imutex
Methanimidamide, N,N'-1,2-ethenediyl-
Methanimidamide, N,N-1,2-ethenediyl-
Miazole
missing
N,N'-1,2-ethenediylmethanimidamide
N,N'-vinyleneformamidine
OmniPur Imidazole - CAS 288-32-4 - Calbiochem
OmniPur(R) Imidazole
Pyrro(b)monazole
pyrro[b]monazole
STR00036
T5M CNJ [WLN]