Name | (R)-3,3'-BIS(3,5-BIS(TRIFLUOROMETHYL)PHE |
Synonyms | (R)-3,3'-BIS(3,5-BIS(TRIFLUOROMETHYL)PHE (R)-3,3''-BIS(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-1,1''-BINAPH-2,2''-DIYL HYDRPHOS |
CAS | 791616-62-1 |
InChIKey | DQORDVSQWPKAQJ-UHFFFAOYSA-N |
Molecular Formula | C36H17F12O4P |
Molar Mass | 772.476 |
Density | 1.63±0.1 g/cm3(Predicted) |
Melting Point | 162-175 °C |
Boling Point | 722.1±70.0 °C(Predicted) |
Appearance | Form Powder, color white to light-yellow |
pKa | 1.09±0.20(Predicted) |
Storage Condition | 2-8°C |
Use | Application (R)-3,3 '-bis (3,5-bis-trifluoromethoxyphenyl)-1,1'-bio-(2-naphthol) phosphate is a chiral binaphthol-phosphate derivative, which can be used as a catalyst for asymmetric Mannich-type reactions, asymmetric hydrophosphorylation reactions and asymmetric azadir reactions. |
Hazard Symbols | Xi - Irritant |
Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
WGK Germany | 3 |
HS Code | 29319090 |
Add (R)-3,3 '-bis (3,5-bis-trifluoromethoxyphenyl)-1,1'-bie-(2-naphthol)(1.91mmol) and pyridine (7.8mmol) to the two-necked egga-shaped flask, and add phosphoryl chloride (2.69mmol) dropwise to it for 7 minutes at room temperature, and then stir for 2 hours. Then heat reflux for 1 hour. The reaction solution is cooled to room temperature, distilled water (1.6ml) is added dropwise, and heated and refluxed for 1.5 hours. Subsequently, it was cooled to room temperature, subjected to reduced-pressure distillation to remove pyridine, and 6M hydrochloric acid (15ml) was added dropwise, and then heated and refluxed for 2 hours. The reaction liquid is cooled to 0°C, filtered, washed with water and dried. Recrystallization with dichloromethane/n-hexane, but the obtained crude product still contains impurities. Thus, it was dissolved in ethanol and reprecipitated with 6 equivalents of hydrochloric acid to give (R)-3,3 '-bis (3,5-bis-trifluoromethoxyphenyl)-1,1'-bie-(2-naphthol) phosphate (0.9g,1.14mM,73%).
optical rotation (optical activity) | [α]20/D -220°, c = 1 in chloroform (typical) |