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CAS RN: 131274-22-1 | 产品编码: T2584
Tri-tert-butylphosphonium Tetrafluoroborate
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| 产品编码 | T2584 |
| 纯度/分析方法 | >98.0%(T) |
| 分子式/分子量 | C__1__2H__2__8BF__4P = 290.13 |
| 外观与形状（20°C） | 固体 |
| 储存温度 | 室温 (15°C以下阴凉干燥处) |
| 包装和容器 | 1G-带有塑料内管的玻璃瓶 （查看图片） |
| CAS RN | 131274-22-1 |
| Reaxys-RN | 8813613 |
| PubChem物质ID | 125307337 |
| MDL编号 | MFCD04039975 |
技术规格
| Appearance | White to Almost white powder to crystal |
| Purity(Iodometric Titration) | min. 98.0 % |
| NMR | confirm to structure |
物性（参考值）
| 熔点 | 261 °C |
GHS
| 象形图 |
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| 信号词 | 危险 |
| 危险性说明 | H302 : 吞咽有害。 H314 : 造成严重皮肤灼伤和眼损伤。 |
| 防范说明 | P501 : 将内装物/容器送到批准的废物处理厂处理。 P260 : 不要吸入粉尘。 P270 : 使用本产品时不要进食、饮水或吸烟。 P264 : 作业后彻底清洗皮肤。 P280 : 戴防护手套/穿防护服/戴防护眼罩/戴防护面具。 P303 + P361 + P353 : 如皮肤（或头发）沾染：立即脱掉所有沾污的衣物。用水清洗皮肤/淋浴。 P301 + P330 + P331 : 如误吞咽：漱口。不要诱导呕吐。 P363 : 沾染的衣服清洗后方可重新使用。 P301 + P312 + P330 : 如误吞咽：如感觉不适，呼叫急救中心/医生。漱口。 P304 + P340 + P310 : 如误吸入：将人转移到空气新鲜处，保持呼吸舒适体位。立即呼叫急救中心/医生。 P305 + P351 + P338 + P310 : 如进入眼睛：用水小心冲洗几分钟。如戴隐形眼镜并可方便地取出，取出隐形眼镜。继续冲洗。立即呼叫急救中心/医生。 P405 : 存放处须加锁。 |
相关法规
| 新化学物质备案回执号 | B1A232216137 |
运输信息
| UN编号 | UN1759 |
| 类别 | 8 |
| 包装类别 | III |
| 监管条件代码(*) |
应用
TCI Practical Example: Buchwald-Hartwig amination using a palladium catalyst and an alkylphosphine ligand
Used Chemicals
Procedure
Aniline (1.0 g, 10.7 mmol) and 4-chlorotoluene (1.4 g, 11.8 mmol) were dissolved in degassed toluene (10 mL) under nitrogen atmosphere. To this solution was added sodium tert-butoxide (1.54 g, 16.1 mmol), tri-tert-butylphosphonium tetrafluoroborate (31.1 mg, 0.1 mmol) and Pd(dba)2 (61.7 mg, 0.1 mmol, 1.5mol%). The reaction mixture was refluxed for 24 h and cooled to room temperature and quenched with H2O (10 mL). The organic phase was separated and washed with brine (10 mL), dried over MgSO4 (10 g), concentrated under reduced pressure to afford the crude product as a brown liquid. The crude product was purified by column chromatography on silica-gel (hexane : ethyl acetate = 95 : 5) to afford the desired product as a pale yellow crystalline solid (1.21 g, 6.6 mmol, 62%).
Experimenter’s Comments
Toluene was degassed by bubbling with N2 gas for 30 min.
The reaction mixture was analyzed by TLC (hexane : ethyl acetate = 1 : 1, Rf = 0.30) and GC.
Analytical Data (4-Methyl-N-phenylaniline)
1H NMR (400 MHz, CDCl3); δ 7.24-7.20 (t, J = 8.7 Hz, 3H), 7.07 (d, J = 8.7 Hz, 2H), 7.00-6.88 (m, 4H), 6.88-6.84 (m, 1H), 5.58 (s, 1H), 2.29 (s, 3H).
Lead Reference
- Tetramethoxybenzene is a Good Building Block for Molecular Wires: Insights from Photoinduced Electron Transfer
Used Chemicals
Procedure
To a 3-necked 300 mL round bottom flask was charged with diphenylamine (5.01 g, 29.6 mmol, 1.0 eq.), 4-chloroanisole (4.48 g, 31.4 mmol, 1.05 eq.) and degassed toluene (150 mL). To this solution was added Pd2(dba)3 (0.287 g, 0.131 mmol, 1 mol%), tri-tert-butylphosphonium tetrafluoroborate (0.198 g, 0.683 mmol, 2 mol%) and sodium tert-butoxide (6.34 g, 66.0 mmol, 2.2 eq.). The reaction mixture was refluxed for 16 hr under nitrogen atmosphere. After cooled to room temperature, the reaction was diluted with CH2Cl2 (300 mL). The suspension was filtered and the filtrate was dried over Na2SO4 and concentrated under reduced pressure to afford the crude and brown solid. The crude product was purified by silica-gel column chromatography (hexane/EtOAc = 99/1 then 8/1) to afford the light brown solid (7.0 g) containing 10 mol% of diphenylamine. Removal of the residual diphenylamine by recrystallization from hexane (55 mL, 60 °C then 15 °C) gave 4-methoxytriphenylamine as a white solid (5.26 g, 65 %).
Experimenter’s Comments
The reaction mixture was monitored by TLC (EtOAc/hexane = 1/10. Starting materials: Rf = 0.36 (diphenylamine), 0.59 (4-chloroanisole); target product: Rf = 0.46).
Analytical Data（4-Methoxytriphenylamine）
1H NMR (400 MHz, CD2Cl2); δ 7.26-7.17 (m, 4H), 7.10-6.98 (m, 6H), 6.98-6.91 (m, 2H), 6.89-6.82 (m, 2H), 3.79 (s, 3H).
13C NMR (101 MHz, CD2Cl2); δ 156.72, 148.56, 141.00, 129.39, 127.72, 123.12, 122.15, 115.05, 55.77.
Lead References
- Air-Stable Trialkylphosphonium Salts: Simple, Practical, and Versatile Replacements for Air-Sensitive Trialkylphosphines. Applications in Stoichiometric and Catalytic Processes
- An Air and Thermally Stable One- Component Catalyst for the Amination of Aryl Chlorides
Other References
- A Simple Catalytic Method for the Conversion of Aryl Bromides to Arylamines
- Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in the absence of tin reagents
- Air-stable trialkylphosphonium salts
应用
TCI Practical Example: Buchwald-Hartwig Amination Using Pd2(dba)3 and tBu3P・HBF4
应用
Air-stable Tri-tert-butylphosphone Equinalent
References
参考文献
TCIMail
[TCIMAIL No.150] Air-Stable Tri-tert-butylphosphine Equivalent[产品拾贝] Air-stable Tri-tert-butylphosphine Equivalent
[TCI应用实例] 使用Pd2(dba)3和tBu3P·HBF4的Buchwald-Hartwig 胺化反应
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