2-Methylindole
2-METHYL-1H-INDOLE · 1H-INDOLE, 2-METHYL- · NSC 7514 · AURORA 15496 · METHYLKETOLE · a-Methylindol · -Methylindole · 2-METHYLINDOLE
Identifiers & Physical Properties
| CAS No. | 95-20-5 |
|---|---|
| Molecular formula | C9H9N |
| Average molar mass | 131.17 g/mol |
| Monoisotopic mass | 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 |
Chemical & Physical Properties
| XLogP | 2.5 |
|---|---|
| Topological polar surface area | 15.8 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 0 |
| Rotatable bonds | 0 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 122 |
| Chemical classes | Nitrogen Compounds -> Indoles |
| SpringerMaterials Properties | Angular frequency |
| LogP (partition coefficient) | 2.53 |
| Food additives | Food |
| Flavoring agents | EU Flavoring substances |
| Vapor pressure | 0.00603 [mmHg] |
| Physical Description | Off-white crystalline solid[Alfa Aesar MSDS] |
| Melting point | 57-59 °C (lit.) |
| Boiling point | 273 °C (lit.) |
| Density | 1,07 g/cm3 |
| Refractive index | 1.6070 (estimate) |
| FLAVIS Number | 14.131 | 2-Methylindole |
| Flash point | 141 °C |
| Storage conditions | Keep in dark place,Inert atmosphere,Room temperature |
| Solubility | Chloroform (Sparingly), Methanol (Slightly)Insoluble in water. |
| pKa (acidity coefficient) | 17.57±0.30(Predicted) |
| Physical state | Crystals, Flakes, or Crystalline Powder |
| Color | Yellow to reddish-purple or brown |
| Odor | at 0.10 % in dipropylene glycol. animal indole fresher than skatole with no fecal odor |
| Odor type | animal |
| Sensitivity | Light Sensitive |
| 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 (partition coefficient) | 2.530 |
| CAS DataBase Reference | 95-20-5(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | I7CN58827I |
| NIST Chemistry Reference | 1H-Indole, 2-methyl-(95-20-5) |
| EPA Substance Registry System | 1H-Indole, 2-methyl- (95-20-5) |
| UNSPSC Code | 12352200 |
| NACRES | NA.24 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302 |
| GHS precautionary statements | P264-P270-P301+P312-P501 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xn,Xi |
| Risk statements (R) | 20/21/22-41 |
| Safety statements (S) | 36/37-24/25-39-26 |
| UN transport number | 3335 |
| Water hazard class (WGK) | 3 |
| RTECS number | NM0345000 |
| F | 8-10-13-23 |
| TSCA inventory status | TSCA listed |
| Customs code | 29339990 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Acute Tox. 4 Oral |
Safety & Regulations
| GHS classification | 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. |
|---|---|
| Regulatory information | 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 |
| Hazards summary | 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 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | NM0345000 |
| UN transport number | 3335 |
| Customs code | 29339990 |
| Risk statements (R) | 20/21/22-41 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn,Xi |
| Safety statements (S) | 36/37-24/25-39-26 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H302 |
| Hazard class | Acute Tox. 4 Oral |
| GHS precautionary statements | P264-P270-P301+P312-P501 |
Applications & Uses
Uses
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.
Uses
2-Methylindole is used as a reactant for regioselective synthesis of oxopyrrolidine analogs via iodine-catalyzed Markovnikov addition reaction, Friedel-Crafts alkylation reactions, preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators, Michael addition reactions and in synthesis of cyclooxygenase-1 (COX-1)/cyclooxygenase-2 (COX-2) inhibitors.
Preparation & Synthesis
Preparation
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.