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CAS RN: 563-41-7 | 产品编码: S0032
Semicarbazide Hydrochloride
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技术规格
| Appearance | White to Almost white powder to crystal |
| Purity(Bromination Method) | min. 99.0 % |
物性（参考值）
| 溶解性（微溶于） | 醇 |
| 溶解性（不溶于） | 乙醚 |
GHS
| 象形图 |
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| 信号词 | Danger |
| 危险性说明 | H301 : Toxic if swallowed. H315 : Causes skin irritation. H319 : Causes serious eye irritation. H361 : Suspected of damaging fertility or the unborn child. H373 : May cause damage to organs through prolonged or repeated exposure. |
| 防范说明 | P501 : Dispose of contents/ container to an approved waste disposal plant. P260 : Do not breathe dust/ fume/ gas/ mist/ vapors/ spray. P270 : Do not eat, drink or smoke when using this product. P202 : Do not handle until all safety precautions have been read and understood. P201 : Obtain special instructions before use. P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection. P302 + P352 : IF ON SKIN: Wash with plenty of water. P308 + P313 : IF exposed or concerned: Get medical advice/ attention. P337 + P313 : If eye irritation persists: Get medical advice/ attention. P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P362 + P364 : Take off contaminated clothing and wash it before reuse. P332 + P313 : If skin irritation occurs: Get medical advice/ attention. P301 + P310 + P330 : IF SWALLOWED: Immediately call a POISON CENTER/doctor. Rinse mouth. P405 : Store locked up. |
相关法规
| RTECS# | VT3500000 |
运输信息
| UN编号 | UN2811 |
| 类别 | 6.1 |
| 包装类别 | III |
| HS编码* | 2928.00-000 |
应用
Synthesis of Alkynyl Ketones using Eschenmoser-Tanabe Fragmentation(alternative method)
Typical Procedure:
To a stirred solution of semicarbazide hydrochloride (12.94 g, 116.0 mmol) and sodium acetate trihydrate (0.95 g, 12 mmol) in water (116 mL) is added 1 (2.63 g, 11.6 mmol) at room temperature. Sufficient 95% ethanol is added to bring about a homogenous solution. After stirring at room temperature for 7 h, the reaction mixture is extracted with ethyl acetate. The combined organic phases are washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product is purified by silica gel chromatography (ethyl acetate → ethyl acetate : methanol = 9 : 1) to give 2 (2.92 g, 89%) as a white solid.
Next, to a stirred solution of 2 (1.86 g, 6.57 mmol) in dichloromethane (65.7 mL) is added portionwise 95% lead tetraacetate (6.42 g, 13.8 mmol), maintaining the bath temperature at –10 °C After stirring for 1 h at –10 °C, ethyl acetate is added to the reaction mixture, which is allowed to warm to room temperature. Then the mixture is filtered through a Celite pad and concentrated under reduced pressure. The crude product is purified by silica gel column chromatography (hexane : ethyl acetate = 4 : 1) to give 3 (0.83 g, 60%) as a colorless oil.
To a stirred solution of semicarbazide hydrochloride (12.94 g, 116.0 mmol) and sodium acetate trihydrate (0.95 g, 12 mmol) in water (116 mL) is added 1 (2.63 g, 11.6 mmol) at room temperature. Sufficient 95% ethanol is added to bring about a homogenous solution. After stirring at room temperature for 7 h, the reaction mixture is extracted with ethyl acetate. The combined organic phases are washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product is purified by silica gel chromatography (ethyl acetate → ethyl acetate : methanol = 9 : 1) to give 2 (2.92 g, 89%) as a white solid.
Next, to a stirred solution of 2 (1.86 g, 6.57 mmol) in dichloromethane (65.7 mL) is added portionwise 95% lead tetraacetate (6.42 g, 13.8 mmol), maintaining the bath temperature at –10 °C After stirring for 1 h at –10 °C, ethyl acetate is added to the reaction mixture, which is allowed to warm to room temperature. Then the mixture is filtered through a Celite pad and concentrated under reduced pressure. The crude product is purified by silica gel column chromatography (hexane : ethyl acetate = 4 : 1) to give 3 (0.83 g, 60%) as a colorless oil.
References
- 1)Thermolysis of Δ3-1 ,3,4-oxadiazolin-2-ones and 2-phenylimino-Δ3-l,3,4-oxadiazolinesderived from α,β-epoxyketones. An alternative method for the conversion of α,β-epoxyketones to alkynones and alkynals
- 2)Total Synthesis of (–)-Mersicarpine
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