ETHYL 1-METHYL-1H-IMIDAZOLE-2-CARBOXYLATE CAS 30148-21-1
ETHYL 1-METHYL-1H-IMIDAZOLE-2-CARBOXYLATE Basic information
| Product Name: | ETHYL 1-METHYL-1H-IMIDAZOLE-2-CARBOXYLATE |
| Synonyms: | 2-(Ethoxycarbonyl)-1-methyl-1H-imidazole;1--1H--2-MethyliMidazoleethyl forMate;1--1H- MethyliMidazole-2-ethyl forMate;ETHYL 1-METHYLIMIDAZOLE-2-CARBOXYLATE;ETHYL 1-METHYL-1H-IMIDAZOLE-2-CARBOXYLATE;RARECHEM AL BI 0638;Ethyl 1-methyl-1H-imidazole-2-carboxylate ,97%;1-Methyl-1H-iMidazole-2-carboxylic Acid Ethyl Ester |
| CAS: | 30148-21-1 |
| MF: | C7H10N2O2 |
| MW: | 154.17 |
| EINECS: | |
| Product Categories: | Miscellaneous Reagents |
| Mol File: | 30148-21-1.mol |
ETHYL 1-METHYL-1H-IMIDAZOLE-2-CARBOXYLATE Chemical Properties
| Melting point | 29-31°C |
| Boiling point | 110-111°C/ 0.5 mmHg |
| density | 1.14±0.1 g/cm3(Predicted) |
| storage temp. | 2-8°C |
| solubility | Soluble in dichloromethane, ether, ethyl acetate and methanol. |
| form | Solid |
| pka | 4.00±0.25(Predicted) |
| color | White Crystalline |
| InChI | InChI=1S/C7H10N2O2/c1-3-11-7(10)6-8-4-5-9(6)2/h4-5H,3H2,1-2H3 |
| InChIKey | NOTZYDYZBOBDFE-UHFFFAOYSA-N |
| SMILES | C1(C(OCC)=O)N(C)C=CN=1 |
| CAS DataBase Reference | 30148-21-1 |
Safety Information
| Hazard Codes | T |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| Hazard Note | Irritant |
| HS Code | 29339900 |
| Chemical Properties | White Crystalline Solid |
| Uses | Ethyl 1-methyl-1H-imidazole-2-carboxylate is a useful synthetic intermediate for solid phase synthesis of polyamides containing imidazole. |
| Uses | Ethyl 1-methylimidazole-2-carboxylate is used as a synthetic intermediate for solid phase synthesis of polyamides containing imidazole. |
| Synthesis | 616-47-7 541-41-3 30148-21-1 Synthesis of ethyl 1-methyl-1H-imidazole-2-carboxylate: triethylamine (3.40 mL, 24.4 mmol) and ethyl chloroformate (2.34 mL, 24.4 mmol) were added drop-wise to a solution of 1-methyl-1H-imidazole (1.00 g, 12.2 mmol) in acetonitrile (4.0 mL) at 0 °C. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the mixture was filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure to remove the solvent. The resulting crude product was purified by fast column chromatography (silica gel as stationary phase and hexane/ethyl acetate as eluent) to afford ethyl 1-methyl-1H-imidazole-2-carboxylate (1.50 g, 9.73 mmol, 80% yield) as a white solid. The structure of the product was confirmed by 1H-NMR (400 MHz, CDCl3) and ESI-MS: 1H-NMR δ 1.42 (3H, t, J = 7.2 Hz), 4.01 (3H, s), 4.40 (2H, q, J = 7.2 Hz), 7.01-7.03 (1H, m), 7.13-7.15 (1H, m); ESI-MS m /z = 155 (M + H)+. |
| References | [1] Journal of the American Chemical Society, 1996, vol. 118, # 26, p. 6141 - 6146 [2] Patent: EP3263565, 2018, A1. Location in patent: Paragraph 0386; 0387 [3] Patent: JP2017/66077, 2017, A. Location in patent: Page/Page column 7; 8; 9; 10; 11 [4] Patent: WO2005/33077, 2005, A1. Location in patent: Page/Page column 53 [5] Patent: WO2004/58763, 2004, A1. Location in patent: Page 43 |
ETHYL 1-METHYL-1H-IMIDAZOLE-2-CARBOXYLATE Preparation Products And Raw materials
| Raw materials | Tetrahydrofuran-->n-Butyllithium-->Ethyl chloroformate-->1-Methylimidazole-->Ethyl formate-->Acetonitrile-->Triethylamine |
| Preparation Products | ETHYL 1-METHYL-5-NITROIMIDAZOLE-2-CARBOXYLATE-->Ethyl 1-methyl-4-nitroimidazole-2-carboxylate-->1-Methyl-1H-imidazole-2-carboxylic acid |
