alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol CAS 24155-42-8
alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol Basic information
| Product Name: | alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol |
| Synonyms: | -(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol;1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YL)ETHANOL;1-(2,4-dichlorophenyl)-2-(1-imidazolyl)ethanol;1-(2,4-DICHLOROPHENYL)-2-IMIDAZOL-1-YL ETHANOL;1H-IMIDAZOLE-1-ETHANOL, ALPHA-(2,4-DICHLOROPHENYL)-;ALPHA-(2,4-DICHLOROPHENYL)-1H-IMIDAZOLE-1-ETHANOL;ALPHA-(2,4-DICHLOROPHENYL)-2-1H-IMIDAZOLE-1-ETHANOL;ALPHA-(2,4-DICHLORO PHENYL)-B-(IMIDAZOLE-YL)ETHANOL |
| CAS: | 24155-42-8 |
| MF: | C11H10Cl2N2O |
| MW: | 257.12 |
| EINECS: | 246-042-5 |
| Product Categories: | Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Imidazol&Benzimidazole;Imidazoles;11 |
| Mol File: | 24155-42-8.mol |
alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol Chemical Properties
| Melting point | 134-138 °C |
| Boiling point | 468.5±45.0 °C(Predicted) |
| density | 1.4133 (rough estimate) |
| vapor pressure | 0Pa at 20℃ |
| refractive index | 1.5500 (estimate) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | DMSO (Slightly), Methanol (Slightly) |
| pka | 12.25±0.20(Predicted) |
| form | solid |
| color | White to Pale Yellow |
| Water Solubility | 1300 g/L (20 ºC) |
| InChI | 1S/C11H10Cl2N2O/c12-8-1-2-9(10(13)5-8)11(16)6-15-4-3-14-7-15/h1-5,7,11,16H,6H2 |
| InChIKey | UKVLTPAGJIYSGN-UHFFFAOYSA-N |
| SMILES | OC(Cn1ccnc1)c2ccc(Cl)cc2Cl |
| LogP | 2.31 at 20℃ |
| CAS DataBase Reference | 24155-42-8(CAS DataBase Reference) |
| EPA Substance Registry System | 1H-Imidazole-1-ethanol, ?-(2,4-dichlorophenyl)- (24155-42-8) |
Safety Information
| Hazard Codes | Xn,Xi |
| Risk Statements | 22-36/37/38 |
| Safety Statements | 38-28B-36-26 |
| WGK Germany | 3 |
| RTECS | NI5485000 |
| HS Code | 2933290000 |
| Storage Class | 11 - Combustible Solids |
| Chemical Properties | cream-coloured to beige powder |
| Uses | Intermediate in the preparation of Miconazole.An impurity in the synthesis of Fenticonazole.An impurity in the synthesis of Ketoconazole. |
| Uses | Intermediate in the preparation of Miconazole.An impurity in the synthesis of Fenticonazole.An impurity in the synthesis of Ketoconazole.Econazole EP Impurity A. |
| Application | In the pharmaceutical field, alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol is an important precursor for the synthesis of various imidazole antifungal drugs (such as econazole and miconazole), which are widely used to treat fungal infections. Furthermore, it is an intermediate in the production of agricultural fungicides (such as imidazoles), which are used in agriculture to control various plant diseases, such as powdery mildew and black rot, thereby increasing crop yields. |
| Flammability and Explosibility | Not classified |
| Synthesis | 46503-52-0 24155-42-8 General procedure for the synthesis of alpha-(2,4-dichlorophenyl)-1H-imidazole-1-ethanol from 2'-(1H-imidazol-1-yl)-2,4-dichloroacetophenone: In a 1000 mL three-necked flask equipped with a stirrer, a thermometer, and a dropping funnel, add 102 g of 2'-(1H-imidazol-1-yl)-2,4-dichloroacetophenone (0.4 mol) and 300 mL of methanol. Potassium borohydride was added in batches and slowly heated to reflux. After completion of the reaction, stirring was continued for 1 h and the progress of the reaction was monitored by thin layer chromatography (TLC) (unfolding agent was ethyl acetate: methanol = 10:1, v/v). At the end of the reaction, methanol was recovered by distillation under reduced pressure. The concentrate was adjusted to pH 4-5 with 5% hydrochloric acid solution and subsequently diafiltrated. The filtrate was adjusted pH to 7-8 with 5% sodium bicarbonate solution, when a white solid precipitated. The solid was collected by filtration, washed with water, dried and recrystallized to give 93.1 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol in 90.5% yield with a melting point of 134-135 °C. |
| References | [1] Patent: CN102180835, 2016, B. Location in patent: Paragraph 0015; 0016 [2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1665 - 1674 [3] Polyhedron, 2013, vol. 52, p. 106 - 114 [4] Organic and Biomolecular Chemistry, 2018, vol. 16, # 23, p. 4288 - 4294 [5] Medicinal Chemistry Research, 1999, vol. 9, # 3, p. 162 - 175 |
alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol Preparation Products And Raw materials
| Raw materials | 1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOLE-1-YL) ETHANONE-->1-Butanaminium, N,N,N-tributyl-, salt with 1H-imidazole (1:1)-->Imidazole-->ALPHA-(CHLOROMETHYL)-2,4-DICHLOROBENZYL ALCOHOL-->α-(Bromomethyl)-2,4-dichlorobenzenemethanol-->(2,4-dichlorophenyl)oxirane-->Potassium borohydride-->Methanol |
| Preparation Products | Imazalil-->1-(2-(2-(4-Chlorophenoxy)ethoxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imida zole nitrate-->Isoconazole |
