|
|
| | Tri-tert-butylphosphine tetrafluoroborate Basic information | | Reaction |
| | Tri-tert-butylphosphine tetrafluoroborate Chemical Properties |
| Melting point | 261 °C(lit.) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly) | | form | Crystals and Chunks | | color | White | | Water Solubility | Soluble in methylene chloride and chloroform. Slightly soluble in terahydro furan. Insoluble in hexane, toluene and water. | | Sensitive | Hygroscopic | | BRN | 8813613 | | InChI | InChI=1S/C12H28P.BF4/c1-10(2,3)13(11(4,5)6)12(7,8)9;2-1(3,4)5/h13H,1-9H3;/q2*-1 | | InChIKey | YSTLBJVHZMEEAC-UHFFFAOYSA-N | | SMILES | [P-](C(C)(C)C)(C(C)(C)C)C(C)(C)C.[B-](F)(F)(F)F | | CAS DataBase Reference | 131274-22-1(CAS DataBase Reference) |
| Hazard Codes | Xn | | Risk Statements | 36/37/38-20/21/22 | | Safety Statements | 22-24/25-36/37/39-26 | | RIDADR | UN 1759 8/PG III | | WGK Germany | 3 | | TSCA | No | | HazardClass | 8 | | PackingGroup | III | | HS Code | 29319090 | | Storage Class | 11 - Combustible Solids |
| | Tri-tert-butylphosphine tetrafluoroborate Usage And Synthesis |
| Reaction |
- Air-stable, non-pyrophoric precursor of the Tri-t-butylphosphine ligand which is used in a variety of catalytic processes.
- Ligand for Suzuki cross-couplings.
- Ligand for Heck Reactions.
- Ligand for Stille Cross-couplings.
- Ligand for α-Arylation and vinylation of arylmandelic acid derivatives.
- Ligand for direct arylation of hetercycles
- Synthesis of benzocyclobutenes by C-H activation.
- Cross-coupling of Grignard reagents and aryl bromides.
- Palladium catalyzed annulation of haloanilines.
- Palladium-Catalyzed Acylation.
- Palladium Catalyzed Carbonylative Heck Reaction.
- Palladium-catalyzed aminosulfonylation.
- Palladium-catalyzed intramolecular C–O bond formation.
- Ruthenium-catalyzed cross-coupling of aldehydes with arylboronic acid.
| | Chemical Properties | white to light yellow crystal powde | | Uses | Tri-tert-butylphosphonium Tetrafluoroborate is used in the synthesis of substituted biaryl compounds via palladium catalyzed tandem Heck-direct arylation and tandem- sequential Heck-direct arylation-hydrogenation. Also used in the synthesis of a novel organic dye with fluorenone as conjugation bridge which is used in dye sensitized solar cells. | | Uses | suzuki reaction
Hindered Phosphine salt employed with a Pd(0)-15-membered, triolefinic, macrocyle in Suzuki cross-coupling reactions of aryl bromides and chlorides. Also used in Heck coupling of non-activated vinyl tosylates with electron deficient olefins.
Ligand used in the Pd-catalyzed enantioselective αarylation of N-boc-pyrrolidine. | | Preparation | Addition of HBF4 to a solution of tri-tert-butylphosphine in methylene chloride. Separation of the organic layer and removal of the solvent gives analytically pure Tri-tert-butylphosphine tetrafluoroborate.
| | Application | Tri-tert-butylphosphonium tetrafluoroborate is a ligand used in the palladium-catalyzed enantioselective alfa-arylation of N-boc-pyrrolidine. It is also used with a palladium(0)-15-membered, triolefinic, macrocyle in Suzuki cross-coupling reactions of aryl bromides and chlorides. Further, it is used in the Heck coupling of vinyl tosylates with olefins. | | reaction suitability | reaction type: Cross Couplings
reagent type: ligand
reaction type: Addition Reactions
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: Carbonylations
reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Sonogashira Coupling
reagent type: ligand
reaction type: Stille Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling | | storage | Tri-tert-butylphosphine tetrafluoroborate is indefinitely stable as a solid and in solution and requires no special handling. This compound is considered non-hazardous. Protection from oxygen is required in the presence of the base, as the highly air-sensitive tri-tert-butylphosphine will be formed.
|
| | Tri-tert-butylphosphine tetrafluoroborate Preparation Products And Raw materials |
|