2-Methylbenzimidazol
2-METHYL-1H-BENZO[D]IMIDAZOLE · 2-methyl-benzimidazol · 1H-Benzimidazole, 2-methyl- · MethylbenziMidazole · AKOS 90363 · RARECHEM AQ NN 0067 · 2-METHYLENZIMIDAZOLE · 2-METHYLBENZIMIDAZOLE
Identifikatoren & physikalische Daten
| CAS No. | 30304-58-6 |
|---|---|
| Summenformel | C8H8N2 |
| Durchschnittliche Molmasse | 132,16 g/mol |
| Monoisotopische Masse | 132,06874826 g/mol |
| SMILES | Cc1nc2ccccc2[nH]1 |
| InChIKey | LDZYRENCLPUXAX-UHFFFAOYSA-N |
| PubChem CID | 11984 |
| ChEMBL | CHEMBL309135 |
| ChEBI | CHEBI:194887 |
| EC No. | 210-411-9 |
| DTXSID | DTXSID5060641 |
| Lokaler Name | 2-Methylbenzimidazol |
Chemische & physikalische Eigenschaften
| XLogP | 2,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 28,7 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 124 |
| Stoffklassen | Nitrogen Compounds -> Imidazoles |
| SpringerMaterials Properties | Chemical shift |
| LogP (Verteilungskoeffizient) | 1.84 |
| Dampfdruck | 0.0000274 [mmHg] |
| Physical Description | Beige crystalline solid[Sigma-Aldrich MSDS] |
| Schmelzpunkt | 175-177 °C (lit.) |
| Siedepunkt | 234.08°C (rough estimate) |
| Dichte | 1.1083 (rough estimate) |
| Brechungsindex | 1.6013 (estimate) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Löslichkeit | DMSO (Slightly), Methanol (Slightly)slightly soluble |
| pKa (Säurekonstante) | 6.19(at 25℃) |
| Aggregatzustand | Crystalline Powder |
| Farbe | Light beige to brown |
| BRN | 112264 |
| InChI | 1S/C8H8N2/c1-6-9-7-4-2-3-5-8(7)10-6/h2-5H,1H3,(H,9,10) |
| InChIKey | LDZYRENCLPUXAX-UHFFFAOYSA-N |
| SMILES | Cc1nc2ccccc2[nH]1 |
| CAS Datenbank | 615-15-6(CAS DataBase Reference) |
| NIST chemische Informationen | 1H-benzimidazole, 2-methyl-(615-15-6) |
| EPA chemische Informationen | 1H-Benzimidazole, 2-methyl- (615-15-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302 (89.6%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 48 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 1H-Benzimidazole, 2-methyl-1H-Benzimidazole, 2-methyl-: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | An irritant that may cause serious eye injuryHarmful by ingestion[Sigma-Aldrich MSDS] See Benzimidazole. |
| Hazard Classes and Categories | Acute Tox. 4 (89.6%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29339990 |
| RTECS-Nr. | DD9100000 |
| R-Sätze (R) | 22-37/38-41-20/21/22 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26-39-45-44 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 OralEye Dam. 1Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Verwenden
2-Methylbenzimidazole is an important pharmacophore widely used in medicinal chemistry for the synthesis of various antibacterial and antifungal agents.It can be used as a key precursor to synthesize substituted benzimidazo[1,2-a]quinolones.It can be used in the synthesis of reversible solid-to-liquid phase transition coordination polymer crystals.2-Methylbenzimidazole also exhibits corrosion inhibition.
Herstellung & Synthese
synthetische
2-Methylbenzimidazole is synthesized by the condensation of o-phenylenediamine with acetic acid. The mixture of o-phenylenediamine and acetic acid is heated at 100°C for 2 hours and then cooled slowly. 10% sodium hydroxide solution is added slowly to the mixture until it is slightly alkaline. The mixture is filtered and washed with cold water. The crude product is then recrystallized with water and decolorized with activated charcoal to obtain the final product. The yield is 68%.