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Imidazol
1H-IMIDAZOLE · Imidazol · IMD · IMZ · IMINAZOLE · GLYOXALINE · LMIDAZOLE · Imidazoie
Identifikatoren & physikalische Daten
| CAS No. | 288-32-4 |
|---|---|
| Summenformel | C3H4N2 |
| Durchschnittliche Molmasse | 68,08 g/mol |
| Monoisotopische Masse | 68,03744813 g/mol |
| SMILES | c1c[nH]cn1 |
| InChIKey | RAXXELZNTBOGNW-UHFFFAOYSA-N |
| PubChem CID | 795 |
| ChEMBL | CHEMBL540 |
| ChEBI | CHEBI:16069 |
| EC No. | 206-019-2 |
| DTXSID | DTXSID2029616 |
| Lokaler Name | Imidazol |
Chemische & physikalische Eigenschaften
| XLogP | -0,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 28,7 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 28,1 |
| Stoffklassen | Nitrogen Compounds -> Imidazoles |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Kosmetika | Buffering |
| pH | pH 10.5 for 38 g/L at 20 °C9.5-11.0 (25℃, 50mg/mL in H2O) |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| Pestizide | Environmental transformation -> Pesticide transformation products (metabolite, successor) |
| LogP (Verteilungskoeffizient) | log Kow = -0.08-0.02 |
| Geruch | Amine-like odor |
| Dichte | Density: 1.0303 g/cu m at 101 °CRelative density (water = 1): 1.031.0303 @ 101°C1.01 g/mL at 20 °C |
| Viscosity | 2.617 mm²/s at 100 °C |
| Color/Form | Monoclinic prisms from benzeneColorless crystalsColorless-yellow solid |
| Löslichkeit | Very soluble in waterIn water, 241 g/100 g at 20 °CIn water, 2060 g/kg H2O at 19 °CIn water, 663 g/L at 20 °CVery soluble in ethanolsoluble in diethyl ether, acetone, pyridineslightly soluble in benzeneSolubility in water, g/100ml at 20 °C: 63.3 (good)H2O: 0.1 M at 20 °C, clear, colorless633 g/L (20 ºC) |
| Schmelzpunkt | 88-91 °C(lit.) |
| Siedepunkt | 256 °C(lit.) |
| Dampfdruck | <1 mm Hg ( 20 °C) |
| Brechungsindex | 1.4801 |
| Flammpunkt | 293 °F |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | 6.953(at 25℃) |
| Aggregatzustand | crystalline |
| Farbe | white |
| Wichte | 1.03 |
| Geruch | Amine like |
| Merck | 14,4912 |
| BRN | 103853 |
| Henry-Konstante | 3.3×103 mol/(m3Pa) at 25℃, Du et al. (2017) |
| Dielektrizitätskonstante | 23.0(Ambient) |
| Stabilität | Stable. Incompatible with acids, strong oxidizing agents. Protect from moisture. |
| Kosmetik-Inhaltsstoffe Funktionen | BUFFERING |
| InChI | 1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5) |
| InChIKey | RAXXELZNTBOGNW-UHFFFAOYSA-N |
| SMILES | c1c[nH]cn1 |
| LogP (Verteilungskoeffizient) | -0.02 at 25℃ |
| CAS Datenbank | 288-32-4(CAS DataBase Reference) |
| NIST chemische Informationen | 1H-Imidazole(288-32-4) |
| EPA chemische Informationen | Imidazole (288-32-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P318, P321, P330, P363, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.2% (2 of 945) of reports.H302 (97.9%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Chemical: 1H-ImidazoleHazard Traits - Reproductive Toxicity1H-Imidazole is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1H-Imidazole are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 21-08-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/2052Imidazole: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 1H-Imidazole: Human health tier II assessment |
| Brandgefahren | Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. |
| Brandpotenzial | Combustible. |
| Gefahrenübersicht | Corrosive to skin and irritating to eyes in rabbits--may cause permanent eye injuryA 90-day oral study of rats showed histopathological changes of the liver and kidney at 180 mg/kg/dayNo evidence of neurotoxicityNo effects on sperm parameters or toxicity to male or female reproductive organs observed in the 90-day studyTeratogenicity and developmental toxicity observed at doses maternally toxic in rats[OECD SIDS] No increase in abnormalities of offspring in rats dosed 240 mg/kg by gavage during embryogenesis (non-standard study, no information on maternal toxicity)[REPROTOX] Causes burnsInhalation may cause corrosive injuries to upper respiratory tract and lungsHarmful by ingestionMay be toxic to human reproduction and cause harm to the unborn child[Sigma-Aldrich MSDS] |
| UN-Einstufung | UN Hazard Class: 8UN Pack Group: III |
| Chemical Dangers | Decomposes on burning. This produces toxic fumes including nitrogen oxides. The solution in water is a weak base. Reacts violently with strong acids. |
| Physical Dangers | Dust explosion possible if in powder or granular form, mixed with air. |
| Packaging and Labelling | Do not transport with food and feedstuffs. |
| Toxic Combustion Products | Gives off irritating or toxic fumes (or gases) in a fire. |
| Hazard Classes and Categories | Acute Tox. 4 (97.9%)Acute toxicity (ingestion) - category 4Acute toxicity (Oral) - Category 4Reproductive toxicity - Category 1BRepr. 1B |
| Explosive Limits and Potential | Dust explosion possible if in powder or granular form, mixed with air. |
| Brandbekämpfung | Use water spray, foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer immediately for medical attention.Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.Rinse mouth. Rest. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer immediately for medical attention. |
| Sichere Lagerung | Separated from strong acids and food and feedstuffs. |
| Brandbekämpfungsverfahren | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.Use water spray, foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| Lagerbedingungen | 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.Separated from strong acids and food and feedstuffs. |
| Reinigungsverfahren | ACCIDENTAL RELEASE MEASURES: 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: complete protective clothing including self-contained breathing apparatus. Sweep spilled substance into covered containers. Then wash away with plenty of water. |
| Entsorgungsverfahren | SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.Product: Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material 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 companyContaminated packaging: Dispose of as unused product. |
| Verschüttetes entsorgen | Personal protection: complete protective clothing including self-contained breathing apparatus. Sweep spilled substance into covered containers. Then wash away with plenty of water. |
| Preventive Measures | ACCIDENTAL RELEASE MEASURES: 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.Precautions for safe handling: Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.For more Preventive Measures (Complete) data for Imidazole (7 total), please visit the HSDB record page. |
| Eye Prevention | Wear face shield or eye protection in combination with breathing protection if powder. |
| Fire Prevention | NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust. |
| Inhalation Risk | No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 19(SRC), determined from a log Kow of -0.08(2) and a regression-derived equation(3), indicates that imidazole is expected to have very high mobility in soil(SRC). The pKa of imidazole is 7.0(4), indicating that this compound will exist partially in cation form and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of the neutral species of imidazole from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 3.8X10-6 atm-cu m/mole(6)(SRC), using a fragment constant estimation method(6). Imidazole's neutral species is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.44X10-2 mm Hg at 25 °C(SRC), determined from a fragment constant method(3). Volatilization is not expected for the cationic form because cations do not volatilize(SRC). A 90% of theoretical BOD using activated sludge in the Japanese MITI test(7) suggests that biodegradation is an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 19(SRC), determined from a log Kow of -0.08(2) and a regression-derived equation(3), indicates that imidazole is not expected to adsorb to suspended solids and sediment(SRC). Volatilization of the neutral species from water surfaces may be expected(4) based upon an estimated Henry's Law constant of 3.8X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 8 days and 62 days, respectively(SRC). A pKa of 7.0(6) indicates imidazole will exist partially in the cation form at pH values of 5 to 9 and, therefore, volatilization of the ion from water surfaces is not expected to be an important fate process because cations do not volatilize(SRC). According to a classification scheme(7), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 90% of theoretical BOD using activated sludge in the Japanese MITI test(8) suggests that biodegradation is an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), imidazole, which has an estimated vapor pressure of 4.44X10-2 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase imidazole is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 11 days(SRC), calculated from its rate constant of 3.6X10-11 cu cm/molecule-sec at 25 °C(3). Imidazole does not absorb at light wavelengths >240 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight, since sunlight consists of wavelengths above 290 nm(SRC). |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Expositionspfade | The substance can be absorbed into the body by ingestion. |
| Toxizitätsübersicht | IDENTIFICATION AND USE: Imidazole, an organic alkaloid, is an important pharmacophore in drug discovery. Imidazole is used as a Karl Fischer reagent in analytical chemistry and a reagent in synthetic organic chemistry. It is also used in the biological control of pests, especially fabric-feeding insects, often in combination with dl-p-fluorophenylalanine. HUMAN STUDIES: Autophagic events are induced by imidazole in HEC-1B cells. Accumulation of autophagic vacuoles in imidazole-treated cells was verified by conversion of LC3 protein, as well as confocal and transmission electron microscopy. Furthermore, imidazole blocked autophagic degradation by impairing maturation of autophagosomes into autolysosomes. Concurrently, imidazole treatment induced apoptosis in HEC-1B cells, accompanied by activation of caspase 9 and 3. The proapoptotic effect was mediated by increased Bim expression. Moreover, imidazole upregulated the protein level of FoxO3a and induced its increased nuclear localization. In addition, siRNA-mediated silencing of FoxO3a effectively attenuated imidazole-induced Bim upregulation and cell death, indicating direct involvement of this pathway in the imidazole-induced apoptosis. ANIMAL STUDIES: When 80% Imidazole was applied to the intact rabbit skin as an aqueous paste for 1 or 4 hours under occlusive dressing skin reactions were noted as early as one hour after removal of the dressing. Focal necrosis developed overnight in all animals and was described as leather-like at the end of the observation period. The application of 0.1 g of unchanged imidazole to the rabbit's eye (Draize test) affected conjunctiva, cornea, and the nictating membrane of the animals. In rats, the symptoms of acute oral exposure were described as convulsions and disequilibria with lateral posture. Deaths occurred within one day. Apathy and accelerated respiration was noted in survivors. Imidazole was given daily by gavage to rats at 20, 60, and 180 mg/kg bodyweight per day. Liver and the male kidney were identified as target organs in the animal groups receiving 180 mg/kg bw per day as substantiated by significantly increased relative liver weights in males and females which correlated with minimal to slight centrilobular liver cell hypertrophy in males and females, and by a significant increase of absolute and relative kidney weight in high-dose males that was accompanied by an accumulation of alpha2u-microglobulin in the epithelia and lumina of the proximal tubules of the male rat renal cortex. No changes of the male and female reproductive organs including sperm quality were noted in a rat 3-month study. In a developmental study in rats, the incidence of external malformations (anasarca and/or cleft palate) was significantly increased. About 10% of the high dose fetuses (180 mg/kg) were affected while no such changes were observed in the control. Skeletal malformations were also statistically significantly increased: 7.8% affected fetuses per litter were noted in the high dose group compared to 1.1% in the control. The incidences of shortened scapula, bent radius, bent ulna, malpositioned and bipartite sternebrae were statistically significantly increased. Soft tissue variations (dilated renal pelvis and ureter) were significantly increased in fetuses from high dose dams compared to controls (27% vs. 6.4%). The incidences of skeletal variations, mainly delays of the ossification process, were statistically significantly increased from 91% in the control group to 98.4% in the high dose group. Imidazole was not mutagenic when tested with Salmonella typhimurium TA 1535, TA 100, TA 1537, and TA 98 both in the presence and absence of metabolic activation. |
| Signs and Symptoms | Cough. Sore throat. Burning sensation.Redness. Pain. Serious skin burns.Redness. Pain. Blurred vision. Temporary loss of vision.Sore throat. Burning sensation in the throat and chest. |
| Ongoing Test Status | EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPAICSS Dashboard ApplicationAvailable from, as of August 9, 2018: http://actor.epa.gov/dashboard/] |
| Soil Adsorption/Mobility | The Koc of imidazole is estimated as 19(SRC), using a log Kow of -0.08(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that imidazole is expected to have very high mobility in soil. The first pKa of imidazole is 7.0(4), indicating that this compound will exist partially in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). |
| Human Toxicity Excerpts | /ALTERNATIVE and IN VITRO TESTS/ Imidazole, an organic alkaloid, is an important pharmacophore in drug discovery. Anti-neoplastic potential of imidazole derivatives has been documented in several studieshowever, mechanisms by which tumor cells respond to these stimuli remain to be elucidated. Autophagy and apoptosis have key roles in tumorigenesis and tumor treatment. In this study, we systematically examined autophagic events induced by imidazole in HEC-1B cells. Accumulation of autophagic vacuoles in imidazole-treated cells was verified by conversion of LC3 protein, as well as confocal and transmission electron microscopy. Furthermore, imidazole blocked autophagic degradation by impairing maturation of autophagosomes into autolysosomes. Concurrently, imidazole treatment induced apoptosis in HEC-1B cells, accompanied by activation of caspase 9 and 3. The proapoptotic effect was mediated by increased Bim expression. Moreover, imidazole upregulated the protein level of FoxO3a and induced its increased nuclear localization. In addition, siRNA-mediated silencing of FoxO3a effectively attenuated imidazole-induced Bim upregulation and cell death, indicating direct involvement of this pathway in the imidazole-induced apoptosis. Taken together, our data provided a molecular link between imidazoles and anticancer therapiesunderstanding of these properties of imidazole is essential for development of effective cancer therapeutics using imidazoles. |
| Artificial Pollution Sources | Imidazole's production and use as a chemical intermediate in the production of pharmaceuticals, pesticides, dye intermediates, auxiliaries for textile dyeing and finishing, photographic chemicals and corrosion inhibitors(1), and its use as a buffering agent in cosmetics(2) may result in its release to the environment through various waste streams(SRC). Imidazole has been identified as a constituent of tobacco, tobacco smoke, and tobacco smoke substitute(3). |
| Environmental Biodegradation | AEROBIC: Imidazole, present at 100 mg/L, reached 90% of its theoretical BOD(NH3) in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(1). Other screening studies give similar results, imidazole reached 98% degradation after 18 days meeting the 10-day window criteria in the OECD 301A DOC Die-Away test(2), and is confirmed to be readily biodegradable. |
| Environmental Bioconcentration | An estimated BCF of 3 was calculated in fish for imidazole(SRC), using a log Kow of -0.08(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for the neutral species of imidazole is estimated as 3.8X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that the neutral species of imidazole may volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 8 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 62 days(SRC). Imidazole's Henry's Law constant indicates that volatilization of the neutral species from moist soil surfaces may occur(SRC). A pKa of 7.0(3) indicates imidazole will exist partially in the cation form at pH values of 5 to 9 and, therefore, volatilization of the ion from water surfaces is not expected to be an important fate process because cations do not volatilize(SRC). |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2923 8/PG 3 |
| Zollcode | 29332990 |
| RTECS-Nr. | NI3325000 |
| R-Sätze (R) | 36/38-63-34-22-20/21/22-61 |
| Toxizität | LD50 in mice (mg/kg): 610 i.p.1880 orally (Nishie) |
| Gefahrensymbole | C,Xi,T |
| Sicherheitshinweise (S) | 26-36/37/39-45-22-36-27-53 |
| Gefahrenklasse | 8Acute Tox. 4 OralEye Dam. 1Repr. 1BSkin Corr. 1C |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 288-32-4(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 480 °C |
Anwendungen & Verwendung
Beschreibung
Imidazole group denotes a heterocyclic organic compound whose molecule contains a five-membered hetero-aromatic ring of two non-adjacent nitrogen atoms, that a carbon atom is placed between two nitrogen atoms. Imidazole is the universally used trivial name for 1,3-azole. Earlier given names were glyoxaline and iminazole. The importance of this aromatic ring system is reflected by its presence in naturally occurring histidine, histamine and the purines, and in several classes of pharmaceuticals. Imidazole can act as a base and as a weak acid. It exists in two tautomeric forms with the hydrogen atom taking position between the two nitrogen atoms.
History
Imidazole[288-32-4] was first synthesized in 1858 by Debus from ammonia and glyoxal; it was originally named glyoxalin. The name imidazole was introduced by Hantzsch. Industrial production of imidazole began in the 1950s; a wide range of derivatives is now available in industrial quantities.
Herstellung & Synthese
synthetische
Imidazole is formed by reacting glyoxal with formaldehyde in the presence of ammonium acetate in acetic acid. The driving energy is microwave radiation. More generally, this reaction is used to produce substituted imidazoles.Although there had been discoveries of various derivatives of imidazole in 1840, it was first reported in 1858. The synthesis process of imidazole follows the reaction between formaldehyde in ammonia and glyoxal. This process gives low yield of imidazole but it is still used to form imidazole with C-substitution (Wolkenberg et al., 2004).