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| | Tricyclohexyl phosphine Chemical Properties |
| Melting point | 81-83 °C (lit.) | | Boiling point | 383.4±9.0 °C | Condition: Press: 760 Torr | | density | 0.909 g/mL at 25 °C | | Fp | 48 °F | | storage temp. | Inert atmosphere,2-8°C | | solubility | Chloroform (Slightly), DMSO (Slightly, Heated, Sonicaetd), Ethyl Acetate (Slightly) | | form | Solution | | Specific Gravity | 0.9 | | color | White to off-white | | Water Solubility | Soluble in most organic solvents. Insoluble in water. | | Sensitive | Air Sensitive | | Hydrolytic Sensitivity | 8: reacts rapidly with moisture, water, protic solvents | | BRN | 957171 | | Stability: | Air Sensitive, Moisture Sensitive | | InChI | 1S/C18H33P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h16-18H,1-15H2 | | InChIKey | WLPUWLXVBWGYMZ-UHFFFAOYSA-N | | SMILES | C1CCC(CC1)P(C2CCCCC2)C3CCCCC3 | | CAS DataBase Reference | 2622-14-2(CAS DataBase Reference) | | NIST Chemistry Reference | Phosphine, tricyclohexyl-(2622-14-2) | | EPA Substance Registry System | Phosphine, tricyclohexyl- (2622-14-2) |
| | Tricyclohexyl phosphine Usage And Synthesis |
| Description | Tricyclohexyl phosphine is the tertiary phosphine with the formula P( C 6H11) 3. Commonly used as a ligand in organometallic chemistry, it is
often abbreviated to PCy 3, where Cy stands for cyclohexyl. It is
characterized by both high basicity (pK a = 9.7) and a large ligand
cone angle (170°). Tricyclohexyl-phosphine is more basic (and so a
better c-donor) than tribu tyiphosphine, which in turn is more basic
than triphenyl phosphIne. | | Chemical Properties | clear colorless to pale yellow solution | | Uses |
- Tricyclohexyl Phosphine is a ligand catalyst used primarily in organometallic chemistry.
- Ligand used in the Pd-catalyzed coupling of malononitrile with aryl halides.
- suzuki reaction: Bulky phosphine ligand used with a Pd(0)-triolefinic macrocycle catalyst for Suzuki coupling of aryl bromides and chlorides.
- This ligand is applied with Ni as a key intermediate in the formation of cylcopentane compounds.
- As a reagent, Tricyclohexylphosphine is used for a range of metal-catalyzed organic transformations.
- Crabtree's catalyst is an organoiridium compound containing tricyclohexyl phosphine used for hydrogenation of mono-, di-, tri-, and tetra- substituted substrates and hydrogen transfer reactions.
- Grubbs' catalysts consists of transition metal ruthenium and tricylohexyl phosphine utilized in olefin metathesis in synthetic organic chemistry.
| | Uses | Tricyclohexylphosphine is used as a ligand in organometallic chemistry. As a reagent, it is used for a range of metal-catalyzed organic transformations. Crabtree's catalyst is an organoiridium compound containing tricyclohexyl phosphine used for hydrogenation of mono-, di-, tri-, and tetra- substituted substrates and hydrogen transfer reactions. Grubbscatalysts consists of transition metal ruthenium and tricylohexyl phosphine utilized in olefin metathesis in synthetic organic chemistry. | | reaction suitability | reaction type: Cross Couplings
reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Hiyama Coupling
reagent type: ligand
reaction type: Sonogashira Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling | | Synthesis | Triphenylphosphine oxide (1 mmol), dry n-hexane (1 mL) and complexed aluminum hydroxide reagent (1 mmol) were added to the Schlenk tube under nitrogen atmosphere and then the reaction was carried out with stirring at room temperature for 10 minutes. The completion of the reaction mixture was monitored by TLC spot plate and at the end of the reaction, the reaction mixture was filtered through silica gel and the reaction mixture was washed several times with ethyl acetate, the residue obtained from the evaporation of ethyl acetate was separated and purified by silica gel column chromatography using pure cyclohexane to obtain the tricyclohexylphosphine product. | | Purification Methods | It recrystallises from EtOH [Boert et al. J Am Chem Soc 109 7781 1987]. [Beilstein 16 IV 947.] |
| | Tricyclohexyl phosphine Preparation Products And Raw materials |
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