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CAS RN: 564483-18-7 | 产品编码: D5038

2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl


纯度/分析方法: >98.0%(GC)
别名:
  • 2-二环己基膦-2',4',6'-三异丙基联苯
  • 二环己基(2',4',6'-三异丙基-[1,1'-联苯]-2-基)膦
  • Dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine
  • XPhos
产品文档:
1G
¥640.00
3   1   ≥100 
5G
¥2,720.00
6   2   ≥100 
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补充产品信息:

This product is intended for research and development purposes only. It may not be used for (i) any human or veterinary use, including without limitation therapeutic and prophylactic use, (ii) any clinical use, including without limitation diagnostic use. Any use of this product for any of the above mentioned purposes requires a license from the Massachusetts Institute of Technology.

List of Patent Applications and Patents (PDF)

产品编码 D5038
纯度/分析方法 >98.0%(GC)
分子式/分子量 C__3__3H__4__9P = 476.73 
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 564483-18-7
Reaxys-RN 9448497
PubChem物质ID 354334782
MDL编号

MFCD04117682

技术规格
Appearance White to Almost white powder to crystal
Purity(GC) min. 98.0 %
Melting point 186.0 to 190.0 °C
物性(参考值)
熔点 186 °C
溶解性(可溶于) 氯仿
GHS
象形图 Pictogram
信号词 警告
危险性说明 H315 : 造成皮肤刺激。
H319 : 造成严重眼刺激。
防范说明 P264 : 作业后彻底清洗皮肤。
P280 : 戴防护手套/戴防护眼罩/戴防护面具。
P302 + P352 : 如皮肤沾染:用水充分清洗。
P337 + P313 : 如仍觉眼刺激:求医/就诊。
P305 + P351 + P338 : 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。
P362+P364 : 脱掉沾污的衣服,清洗后方可重新使用。
P332 + P313 : 如发生皮肤刺激:求医/就诊。
相关法规
新化学物质备案回执号 B1A232215479
运输信息
监管条件代码(*)
应用
TCI Practical Example: Buchwald-Hartwig amination using Pd2(dba)3 and XPhos as catalysts

Used Chemicals

Procedure

1,4-Dichlorobenzene (500 mg, 3.40 mmol) and piperidine (869 mg, 10.2 mmol) were dissolved in degassed toluene (15.0 mL). To this solution was added sodium tert-butoxide (817 mg, 8.50 mmol), XPhos (65 mg, 0.136 mmol, 4 mol%) and Pd2(dba)3 (47 mg, 0.051 mmol, 1.5 mol%). The reaction was refluxed for 16 h and quenched with H2O (15 mL) after cooling to room temperature. The organic phase was separated and washed with H2O (10 mL) and brine (10 mL), dried over Na2SO4 (30 g), concentrated under reduced pressure to afford the crude product as brown solid, which was purified by column chromatography on silica gel (CH2Cl2 100% → CH2Cl2: EtOAc = 30: 70) to afford the product 1 as a pale yellow solid. The obtained solid was dissolved in hexane and decolorized by activated carbon. After removal of activated carbon by filtration, the filtrate was concentrated to afford the product 1 as a white powder (782 mg, 2.66 mmol, 78%).

Experimenter's Comments

Toluene was degassed by refluxing under nitrogen atmosphere.
Completion of the reaction was confirmed by HPLC.
Obtained product was colorized gradually by the exposure of air and light.

Analytical Data(Compound 1)

1H NMR (400 MHz, CDCl3); δ 6.92 (s, 4H), 2.92 (t, J = 5.9, 8H), 1.54 (m, 8H), 1.32 (m, 4H).

Other References


应用
TCI Practical Example: Stille Coupling using Pd(OAc)2 and Xphos

Used Chemicals

Procedure

To a solution of palladium(II) acetate (44.9 mg, 0.200 mmol, 4 mol%), XPhos (143 mg, 0.300 mmol, 6 mol%), cesium fluoride (2.28 g, 15.0 mmol) and 2-chlorophenothiazine (1.17 g, 5.00 mmol) in toluene (15.0 mL) was added tributyl(2-thienyl)tin (2.24 g, 1.90 mL, 6.00 mmol) and the reaction solution was stirred at 80 ºC for 24 h. After reaction mixture was cooled to room temperature, dichloromethane (15 mL) and H2O (15 mL) were added. Separated water phase was extracted with dichloromethane (15 mL) for 3 times. Combined organic layer was dried over MgSO4 (10 g) and concentrated under reduced pressure to afford the crude product as a brown solid. Crude was purified by column chromatography on silica-gel (hexane: EtOAc = 50 : 1 ~ 5 : 1 → dichloromethane) to afford 2-(thiophen-2-yl)-10H-phenothiazine as a yellow solid (990 mg, 3.51 mmol, 70%).

Experimenter's Comments

Completion of the reaction was confirmed by TLC (Hexane:EtOAc = 10:1, Rf: S.M.=0.28 T.M.=0.18) and GC.

Analytical Data(2-(Thiophen-2-yl)-10H-phenothiazine)

1H NMR (400 MHz, CDCl3); δ 7.92 (brs, 1H), 7.42 (dd, J = 0.9, 5.0 Hz, 1H), 7.35 (dd, J = 0.9, 3.6 Hz, 1H), 7.08-7.13 (m, 2H), 6.94-7.03 (m, 4H), 6.73-6.82 (m, 2H).

Lead Reference


应用
TCI Practical Example: Buchwald-Hartwig Amination

Used Chemicals

Procedure

To a 2-necked flask was charged with bis(dibenzylideneacetone)palladium (0) (36 mg, 0.0633 mmol, 1.5 mol%), XPhos (60 mg, 0.127 mmol, 3.0 mol%), sodium tert-butoxide (811 mg, 8.44 mmol, 2.0 equiv.) and toluene (5 mL) under nitrogen atmosphere. The mixture was stirred at room temperature for 5 min. 4-chlorotoluene (0.5 mL, 4.22 mmol, 1.0 equiv.), and morpholine (0.55 mL, 6.33 mmol, 1.5 equiv.) were added in one portion. The resulting mixture was stirred at reflux for 6 h. The reaction mixture was cooled to room temperature and quenched with water (10 mL). The organic layer was washed with water (10 mL), and brine (10 mL), dried with Na2SO4 (20 g) and then concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (hexane : ethyl acetate = 9 : 1) to afford the corresponding compound as an orange solid (700 mg, 94%).

Experimenter's Comments

Toluene was degassed by bubbling with nitrogen gas for 30 min.
The reaction mixture was monitored by GC.

Analytical Data(Compound 1)

1H NMR (400 MHz, CDCl3); δ 7.10 (d, J = 8.7 Hz, 2H), 6.84 (d, J = 8.7 Hz, 2H), 3.87 (t, J = 4.8 Hz, 4H), 3.11 (t, J = 4.8 Hz, 4H), 2.28 (s, 3H).

13C NMR (101 MHz, CDCl3); δ 149.1, 129.7, 129.5, 116.0, 66.9, 49.9, 20.4.

Lead Reference


参考文献


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