57090-88-7
1H-Imidazole-4-carbonitrile
CAS: 57090-88-7
Molecular Formula: C4H3N3
57090-88-7 - Names and Identifiers
| Name | 1H-Imidazole-4-carbonitrile |
| Synonyms | 4-Cyanoimidazole 4-Cyano-1H-imidazole 4-Imidazolecarbonitrile lH-IMidazole-4-carbonitrile 1H-Imidazole-5-carbonitrile 1H-imidazole-5-carbonitrile 1H-IMIDAZOLE-4-CARBONITRILE 1H-Imidazole-4-carbonitrile |
| CAS | 57090-88-7 |
| EINECS | 611-464-4 |
| InChI | InChI=1/C4H3N3/c5-1-4-2-6-3-7-4/h2-3H,(H,6,7) |
57090-88-7 - Physico-chemical Properties
| Molecular Formula | C4H3N3 |
| Molar Mass | 93.09 |
| Density | 1.28±0.1 g/cm3(Predicted) |
| Melting Point | 143.5-144.5 °C |
| Boling Point | 388.1±15.0 °C(Predicted) |
| Flash Point | 130.8°C |
| Vapor Presure | 3.13E-06mmHg at 25°C |
| pKa | 9.17±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.551 |
57090-88-7 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36 - Irritating to the eyes |
| Safety Description | 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| HS Code | 29339900 |
| Hazard Class | IRRITANT |
57090-88-7 - Reference Information
| Overview | 1h-imidazole-4-carbonitrile is a very important pharmaceutical intermediate, the preparation method is only disclosed in US2009/101921234A: 4-imidazolecarboxylate, concentrated ammonia and ammonium chloride react to form 4-amide imidazole, 4-amideimidazole reacts with a cyanating agent to form 1H-imidazole-4-carbonitrile, but its raw material is not easy to obtain and expensive, and is not suitable for industrial production. In order to meet the market demand, it is urgent to research and develop a preparation method of 1H-imidazole-4-carbonitrile with easily available raw materials, simple industrialization process and low cost. |
| preparation | ① preparation of 1h-imidazole-4-formaldehyde, the steps are as follows: In a 500ml four-mouth bottle, 25.1g(0.254mol) of 4-hydroxymethylimidazole and 125.5g of methanol were added sequentially. The mass ratio of 4-hydroxymethylimidazole to methanol was 1:5, add 66.3g(0.762mol) manganese dioxide at room temperature, the molar ratio of 4-hydroxymethylimidazole and manganese dioxide is 1:3, complete feeding, heat up to 70 ℃ and react for 6 hours, then, the reaction solution was cooled to 25 ° C., and manganese sludge was removed by filtration. The filtrate was 1H-imidazole -4-formaldehyde reaction solution (0.229mol), and the yield was 90%. (2) the preparation of 4-oxime imidazole, the steps are as follows: 1H-imidazole -4-formaldehyde reaction solution (0.229mol) obtained in step (1) is stirred and cooled to 25 ℃, Slowly add hydroxylamine hydrochloride 19.1g(0.275mol),1H-imidazole -4-Formaldehyde, hydroxylamine hydrochloride molar ratio of 1:1.2, control temperature 30 ℃, room temperature for 2 hours, A viscous kettle solution of 4-methyloxime imidazole (0.227mol) was obtained with a yield of 99%. The next step was directly synthesized. (3) preparation of 1H-imidazole-4-carbonitrile, the steps are as follows: (2) step to get the viscous kettle solution of 4-(0.227mol), add acetic anhydride 69.5g(0.681mol), the dehydration reaction conditions: 4-oximazole, acetic anhydride molar ratio of 1:3, heating to 100 ℃, heat preservation reaction for 1 hour, distillation of acetic anhydride under reduced pressure, after the end of distillation, control temperature is less than or equal to 30 deg C Dropwise adding 25% sodium hydroxide aqueous solution to adjust the pH value to 8.0, then add ethyl acetate extraction two times, the extraction layers were combined and washed twice with 25% aqueous solution of sodium chloride. After washing, the oil layer was distilled off under reduced pressure, and then dehydrated by adding toluene, After completion of the dehydration, a large amount of solid was precipitated from the toluene, which was filtered. The filter cake was washed with dichloromethane and dried to obtain 17.6g of 1H-imidazole-4-carbonitrile with a content of 97% and a yield of 81%. |
Last Update：2024-04-09 21:04:16
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