DI-1-ADAMANTYLPHOSPHINE Chemical Properties

Melting point:

181-185 °C

Boiling point:

407.8±12.0 °C(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 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

Safety Information

Hazard Codes 

T

Risk Statements 

23/24/25-36/37/38

Safety Statements 

36/37/39-45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

HS Code 

2931.90.9051

HazardClass 

6.1

PackingGroup 

Ⅲ

DI-1-ADAMANTYLPHOSPHINE Usage And Synthesis

Appearance

White Powder

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

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