2-Methylindol
2-METHYL-1H-INDOLE · 1H-INDOLE, 2-METHYL- · NSC 7514 · AURORA 15496 · METHYLKETOLE · a-Methylindol · -Methylindole · 2-METHYLINDOLE
Identifikatoren & physikalische Daten
| CAS No. | 95-20-5 |
|---|---|
| Summenformel | C9H9N |
| Durchschnittliche Molmasse | 131,17 g/mol |
| Monoisotopische Masse | 131,07349929 g/mol |
| SMILES | Cc1cc2ccccc2[nH]1 |
| InChIKey | BHNHHSOHWZKFOX-UHFFFAOYSA-N |
| PubChem CID | 7224 |
| ChEMBL | CHEMBL259419 |
| ChEBI | CHEBI:49402 |
| EC No. | 202-398-3 |
| DTXSID | DTXSID5059117 |
| Lokaler Name | 2-Methylindol |
Chemische & physikalische Eigenschaften
| XLogP | 2,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 15,8 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 0 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 122 |
| Stoffklassen | Nitrogen Compounds -> Indoles |
| SpringerMaterials Properties | Angular frequency |
| LogP (Verteilungskoeffizient) | 2.53 |
| Lebensmittelzusatzstoffe | Food |
| Aromastoffe | EU Flavoring substances |
| Dampfdruck | 0.00603 [mmHg] |
| Physical Description | Off-white crystalline solid[Alfa Aesar MSDS] |
| Schmelzpunkt | 57-59 °C (lit.) |
| Siedepunkt | 273 °C (lit.) |
| Dichte | 1,07 g/cm3 |
| Brechungsindex | 1.6070 (estimate) |
| Flammpunkt | 141 °C |
| Lagerbedingungen | Keep in dark place,Inert atmosphere,Room temperature |
| Löslichkeit | Chloroform (Sparingly), Methanol (Slightly)Insoluble in water. |
| pKa (Säurekonstante) | 17.57±0.30(Predicted) |
| Aggregatzustand | Crystals, Flakes, or Crystalline Powder |
| Farbe | Yellow to reddish-purple or brown |
| Geruch | at 0.10 % in dipropylene glycol. animal indole fresher than skatole with no fecal odor |
| Geruchsart | animal |
| BRN | 109781 |
| InChI | 1S/C9H9N/c1-7-6-8-4-2-3-5-9(8)10-7/h2-6,10H,1H3 |
| InChIKey | BHNHHSOHWZKFOX-UHFFFAOYSA-N |
| SMILES | Cc1cc2ccccc2[nH]1 |
| LogP (Verteilungskoeffizient) | 2.530 |
| CAS Datenbank | 95-20-5(CAS DataBase Reference) |
| NIST chemische Informationen | 1H-Indole, 2-methyl-(95-20-5) |
| EPA chemische Informationen | 1H-Indole, 2-methyl- (95-20-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302 (13.8%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P264+P265, P270, P280, P301+P317, P305+P354+P338, P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 80 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 1H-Indole, 2-methyl-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)2-Methylindole: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Intraperitoneal LD50 (mouse) > 262 mg/kg[RTECS] An irritantHarmful by ingestion[Alfa Aesar MSDS] See 3-Methylindole. |
| Hazard Classes and Categories | Acute Tox. 4 (13.8%) |
| F | 8-10-13-23 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | 3335 |
| Zollcode | 29339990 |
| RTECS-Nr. | NM0345000 |
| R-Sätze (R) | 20/21/22-41 |
| Gefahrensymbole | Xn,Xi |
| Sicherheitshinweise (S) | 36/37-24/25-39-26 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 Oral |
Anwendungen & Verwendung
Verwenden
2-Methylindole is an intermediate in the synthesis of indole derivative with potential antifungal activities. It can be used as a raw material for the preparation of deacetylase (HDAC) inhibitor panobinostat.
Herstellung & Synthese
synthetische
2-Methylindole was synthesized from 2-Acetamidotoluene by the following procedure. 2-Acetamidotoluene was added to the mixture of anhydrous ether and sodium amide, heated to 240-260°C under the protection of nitrogen flow, kept for 10min, a large amount of gas was generated in the reaction, and the reaction ended when the gas stopped escaping, and cooled. Ethanol and warm water were added and heated to decompose the sodium derivative of 2-Methylindole and excess sodium amide. After cooling, it was extracted with ether. The extract was concentrated and then distilled, and the fractions at 119-126°C (0.4-0.53kPa) were collected to obtain 2-Methylindole with a yield of 80%-83%. The product can be purified by methanol recrystallization.