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CAS RN: 81290-20-2 | 產品編碼: T1570
(Trifluoromethyl)trimethylsilane [Trifluoromethylating Reagent]
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純度/分析方法: >97.0%(GC)
別名：
- (三氟甲基)三甲基硅烷 [三氟甲基化試劑]
- (三甲基硅烷基)三氟甲烷
- Ruppert-Prakash試劑
- (Trimethylsilyl)trifluoromethane
- Ruppert-Prakash Reagent
產品文檔：
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技術規(guī)格
| Appearance | Colorless to Light yellow clear liquid |
| Purity(GC) | min. 97.0 % |
物性（參考值）
| 沸點 | 55 °C |
| 閃點 | -32 °C |
| 比重 | 0.96 |
| 折射率 | 1.33 |
GHS
| 象形圖 |
|
| 信號詞 | 危險 |
| 危險性說明 | H225 : 高度易燃液體和蒸氣。 |
| 防范說明 | P501 : 將內裝物/容器送到批準的廢物處理廠處理。 P240 : 容器和裝載設備接地/等勢聯接。 P210 : 遠離熱源/火花/明火/熱表面。禁止吸煙。 P233 : 保持容器密閉。 P243 : 采取防止靜電放電的措施。 P241 : 使用防爆的電氣/通風/照明設備。 P242 : 只能使用不產生火花的工具。 P280 : 戴防護手套/戴防護眼罩/戴防護面具。 P370 + P378 : 火災時：使用干砂、干粉或抗醇泡沫滅火。 P303 + P361 + P353 : 如皮膚（或頭發(fā)）沾染：立即脫掉所有沾污的衣物。用水清洗皮膚/淋浴。 P403 + P235 : 存放在通風良好的地方。保持低溫。 |
相關法規(guī)
| 新化學物質備案回執(zhí)號 | B1A232215762 |
運輸信息
| UN編號 | UN1993 |
| 類別 | 3 |
| 包裝類別 | II |
| 監(jiān)管條件代碼(*) |
應用
Synthesis of Trifluoromethylketones from Weinreb Amides
Typical Procedure:
To a 50 mL round bottom flask equipped with a stir bar is added CsF (0.1512 g, 1.0 mmol, 0.2 eq.). Toluene (2.5 mL) is added to the flask, followed by 4-(tert-butyl)-N-methoxy-N-methylbenzamide (1.11 g, 5.0 mmol, 1 eq.). The flask is sealed with a septum equipped with an inlet needle as an exit valve. The flask is cooled to 0 °C for 10 minutes. Once cooled, TMSCF3 (1.42 g, 10.0 mmol, 2 eq.) is added to the reaction mixture dropwise over a period of ≈ 10 minutes. After completion of addition, the reaction mixture is allowed to stir at 0 °C for 10 minutes. The cooling bath is removed and the reaction mixture is allowed to stir at room temperature overnight. (Upon reaching room temperature, the reaction occurs and is mildly exothermic and gas is evolved.) Reaction progress is monitored by 1H NMR.
Once complete conversion to the silylated intermediate is confirmed, water (5 mL) followed by TBAF (5 mL, 1 M in THF, 1 eq.) is added to the reaction flask. The flask is equipped with a reflux condenser, open to air. The contents are then heated to 50 °C, and allowed to stir at that temperature for 2 hours. Once cooled to room temperature, the reaction mixture is diluted with Et2O (≈ 30 mL), and transferred to a separatory funnel. The organic layer is washed with deionized water (3 × 30 mL), followed with a brine solution (1 × 30 mL). The organic layer is dried with Na2SO4 and the solvent is removed in vacuo by rotary evaporation to yield crude trifluoromethylketone. Further purification is accomplished by flash chromatography (hexane : EtOAc = 8 : 2) to produce the pure CF3 ketone as an orange solid (0.935 g, Y. 81%).
To a 50 mL round bottom flask equipped with a stir bar is added CsF (0.1512 g, 1.0 mmol, 0.2 eq.). Toluene (2.5 mL) is added to the flask, followed by 4-(tert-butyl)-N-methoxy-N-methylbenzamide (1.11 g, 5.0 mmol, 1 eq.). The flask is sealed with a septum equipped with an inlet needle as an exit valve. The flask is cooled to 0 °C for 10 minutes. Once cooled, TMSCF3 (1.42 g, 10.0 mmol, 2 eq.) is added to the reaction mixture dropwise over a period of ≈ 10 minutes. After completion of addition, the reaction mixture is allowed to stir at 0 °C for 10 minutes. The cooling bath is removed and the reaction mixture is allowed to stir at room temperature overnight. (Upon reaching room temperature, the reaction occurs and is mildly exothermic and gas is evolved.) Reaction progress is monitored by 1H NMR.
Once complete conversion to the silylated intermediate is confirmed, water (5 mL) followed by TBAF (5 mL, 1 M in THF, 1 eq.) is added to the reaction flask. The flask is equipped with a reflux condenser, open to air. The contents are then heated to 50 °C, and allowed to stir at that temperature for 2 hours. Once cooled to room temperature, the reaction mixture is diluted with Et2O (≈ 30 mL), and transferred to a separatory funnel. The organic layer is washed with deionized water (3 × 30 mL), followed with a brine solution (1 × 30 mL). The organic layer is dried with Na2SO4 and the solvent is removed in vacuo by rotary evaporation to yield crude trifluoromethylketone. Further purification is accomplished by flash chromatography (hexane : EtOAc = 8 : 2) to produce the pure CF3 ketone as an orange solid (0.935 g, Y. 81%).
References
應用
Nucleophilic Trifluoromethylation
Reference
應用
Difluorocarbene Precursor
Reference
- Synthesis of gem-difluorinated cyclopropanes and cyclopropenes: trifluoromethyltrimethylsilane as a difluorocarbene source
參考文獻
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