| Identification | Back Directory | [Name]
DI-1-ADAMANTYLPHOSPHINE | [CAS]
131211-27-3 | [Synonyms]
Diadamantylphosphine DI-1-ADAMANTYLPHOSPHINE Di-1-adamantylphosphine> Bis(adamant-1-yl)phosphine Di(adamantan-1-yl)phosphine Di-1-adamantylphosphine,97% Di-1-adamantylphosphine 97% Bis(1-adamantyl)phosphine, 98% Di-1-adamantylphosphine,min.97% Di-1-adamantylphosphine, min. 97% Phosphine, bis(tricyclo[3.3.1.13,7]dec-1-yl)- Bis(adamant-1-yl)phosphine, Bis(tricyclo[3.3.1.13,7]dec-1-yl)phosphine | [Molecular Formula]
C20H31P | [MDL Number]
MFCD06658117 | [MOL File]
131211-27-3.mol | [Molecular Weight]
302.43 |
| Chemical Properties | Back Directory | [Melting point ]
181-185 °C | [Boiling point ]
407.8±12.0 °C(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
Powder | [color ]
white | [Sensitive ]
air sensitive | [InChI]
InChI=1S/C20H31P/c1-13-2-15-3-14(1)8-19(7-13,9-15)21-20-10-16-4-17(11-20)6-18(5-16)12-20/h13-18,21H,1-12H2 | [InChIKey]
RRRZOLBZYZWQBZ-UHFFFAOYSA-N | [SMILES]
P(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2 |
| Hazard Information | Back Directory | [Uses]
Di-1-adamantylphosphine is a useful research chemical. | [reaction suitability]
reaction type: Buchwald-Hartwig Cross Coupling Reaction reaction type: Heck Reaction reaction type: Hiyama Coupling reaction type: Negishi Coupling reaction type: Sonogashira Coupling reaction type: Stille Coupling reaction type: Suzuki-Miyaura Coupling reagent type: ligand | [Synthesis]
The general procedure for the synthesis of di-1-adamantylphosphine using bis(1-adamantyl)phosphinic chloride as starting material was as follows: at -10 °C, LiAlH4 (2.54 g, 67.0 mmol) was slowly added to a cooled solution of bis(1-adamantyl)phosphinic chloride (10.00 g, 28.3 mmol) dissolved in dry THF (120 cm3) over 90 min. The reaction mixture was gradually warmed to room temperature and stirred continuously for 20 hours. Subsequently, the gray suspension was re-cooled to -10 °C and a mixed solution consisting of concentrated hydrochloric acid (5 cm3) and degassed water (50 cm3) was slowly added via syringe (due to the exothermic nature of the reaction, the initial rate of addition needed to be very slow), at which point a two-phase system was formed, with solids visible in the lower phase. To further improve the phase separation, concentrated hydrochloric acid (5 cm3) was added. The upper organic phase was removed using a flat cannula and the remaining organic phase was dried with MgSO4 and filtered through a cannula. Volatiles were removed under vacuum to give a white powdery product which was separated in a glove box. The final product yield was 6.00 g in 70% yield. The product showed a single peak (δ=17 ppm) by 31P NMR and was 100% pure. The molecular weight of the product was 302.44. | [References]
[1] Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 102, # 1-4, p. 211 - 216 [2] Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 81, # 1-4, p. 141 - 148 [3] Organometallics, 2018, vol. 37, # 19, p. 3243 - 3247 [4] Patent: US9802185, 2017, B2. Location in patent: Page/Page column 38; 39 [5] J. Gen. Chem. USSR (Engl. Transl.), 1990, vol. 60, # 8.1, p. 1603 - 1606 |
|
|