1-Methylimidazol
N-METHYLIMIDAZOLE · 1-methyl-1h-imidazole · MIM · MeIm · methyl imidazole · 1H-Imidazole, 1-methyl- · N-methylimidazole (1-methylimidazole) · 1-Methylimdazole
Identifikatoren & physikalische Daten
| CAS No. | 616-47-7 |
|---|---|
| Summenformel | C4H6N2 |
| Durchschnittliche Molmasse | 82,1 g/mol |
| Monoisotopische Masse | 82,05309819 g/mol |
| SMILES | Cn1ccnc1 |
| InChIKey | MCTWTZJPVLRJOU-UHFFFAOYSA-N |
| PubChem CID | 1390 |
| ChEMBL | CHEMBL543 |
| ChEBI | CHEBI:113454 |
| EC No. | 210-484-7 |
| DTXSID | DTXSID6052291 |
| Lokaler Name | 1-Methylimidazol |
Chemische & physikalische Eigenschaften
| XLogP | -0,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 17,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 6 |
| Formalladung | 0 |
| Komplexität | 44,8 |
| Stoffklassen | Nitrogen Compounds -> Imidazoles |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Density |
| Dichte | 1.0325 @25 °C1.03 g/mL at 25 °C(lit.) |
| Siedepunkt | 196 °C @760 [mm Hg]198 °C(lit.) |
| Schmelzpunkt | -6 °C−60 °C(lit.) |
| Dampfdruck | 0.47 [mmHg]0.4 mm Hg ( 20 °C) |
| Physical Description | LiquidColorless to yellow hygroscopic liquid[Alfa Aesar MSDS] |
| Dissociation Constants | 6.95 (at 25 °C) |
| Brechungsindex | n20/D 1.495(lit.) |
| Flammpunkt | 198 °F |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | Chloroform (Slightly), Methanol (Slightly)Miscible with water. |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 6.95(at 25℃) |
| Wichte | 1.031 |
| Farbe | Clear colorless to yellow |
| pH | 9.5-10.5 (50g/l, H2O, 20℃) |
| Biologische Quelle | synthetic |
| Explosionsgrenze | 2.7-15.7%(V) |
| BRN | 105197 |
| Henry-Konstante | 6.9×101 mol/(m3Pa) at 25℃, Du et al. (2017) |
| Stabilität | Stable, but moisture sensitive. Incompatible with acids, acid anhydrides, strong oxidizing agents, moisture, carbon dioxide, acid chlorides. |
| InChI | 1S/C4H6N2/c1-6-3-2-5-4-6/h2-4H,1H3 |
| InChIKey | MCTWTZJPVLRJOU-UHFFFAOYSA-N |
| SMILES | Cn1ccnc1 |
| LogP (Verteilungskoeffizient) | -0.19 at 25℃ |
| CAS Datenbank | 616-47-7(CAS DataBase Reference) |
| NIST chemische Informationen | 1H-Imidazole, 1-methyl-(616-47-7) |
| EPA chemische Informationen | 1H-Imidazole, 1-methyl- (616-47-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.1% (1 of 797) of reports.H302 (96.9%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Chemical: 1H-Imidazole, 1-methyl-1H-Imidazole, 1-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1H-Imidazole, 1-methyl- 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: 03-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/100381-Methylimidazole: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | Evaluation - 1H-Imidazole, 1-methyl- |
| Gefahrenübersicht | Causes convulsions in oral and intraperitoneal lethal-dose studies of mice[RTECS] Dermal LD50 (rabbit) = 400-640 mg/kgCauses burnsInhalation may cause corrosive injuries to upper respiratory tract and lungsHarmful by ingestion and skin absorption[Alfa Aesar MSDS] See Imidazole. |
| Hazard Classes and Categories | Acute Tox. 4 (96.9%)Acute toxicity (ingestion) - category 4Acute Tox. 4 * |
| Protective Action Criteria (PAC) | 2.3 [mg/m3]25 [mg/m3]150 [mg/m3] |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| F | 3-10 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3267 8/PG 2 |
| Zollcode | 29332990 |
| RTECS-Nr. | NI7000000 |
| R-Sätze (R) | 21/22-34-19-11-20/21/22-52/53-24-22-40-37-21 |
| Toxizität | LD50 orally in Rabbit: 1144 mg/kg LD50 dermal Rabbit > 400 - < 640 mg/kg |
| Gefahrensymbole | C,Xn,F,T |
| Sicherheitshinweise (S) | 26-36-45-1/2-36/37/39-16-33-29-61 |
| Gefahrenklasse | 8Acute Tox. 3 DermalAcute Tox. 4 OralEye Dam. 1Repr. 2Skin Corr. 1B |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Selbstentzündungstemperatur | 977 °F |
Anwendungen & Verwendung
Verwenden
1-Methylimidazole is an aprotic solvent. It is a derivative of imidazole used in the production of pharmaceuticals, pesticides, ion exchange resins, dye intermediates, textile auxiliaries, photographic chemicals, and corrosion inhibitors. It can also be used as a catalyst for the manufacture of polyurethane and a curing agent for epoxy resins. For example, when 1-methylimidazole is added to an aqueous diethylenetriamine (DETA) solution, high CO2 loading can be achieved through phase separation of the absorbent during CO2 absorption[1].
Herstellung & Synthese
synthetische
1-Methylimidazole is prepared mainly by two routes industrially. The main one is acid-catalysed methylation of imidazole by methanol. The second method involves the Radziszewski reaction from glyoxal, formaldehyde, and a mixture of ammonia and methylamine. (CHO)2 + CH2O + CH3NH2 + NH3 → H2C2N(NCH3)CH + 3 H2O The compound can be synthesized on a laboratory scale by methylation of imidazole at the pyridine-like nitrogen and subsequent deprotonation. Similarly, 1-methylimidazole may be synthesized by first deprotonating imidazole to form a sodium salt followed by methylation. H2C2N(NH)CH + CH3I → [H2C2(NH)(NCH3)CH]I [H2C2(NH)(NCH3)CH]I + NaOH → H2C2N(NCH3)CH + H2O + NaI