131274-22-1 Usage
Description
Tri-tert-butylphosphine tetrafluoroborate is a white to light yellow crystalline powder that serves as a versatile ligand in various chemical reactions, particularly in palladium-catalyzed processes. It is known for its effectiveness in promoting enantioselectivity and facilitating cross-coupling reactions.
Uses
Used in Pharmaceutical Industry:
Tri-tert-butylphosphine tetrafluoroborate is used as a ligand for the palladium-catalyzed enantioselective α-arylation of N-boc-pyrrolidine, which is a crucial step in the synthesis of various pharmaceutical compounds.
Used in Chemical Synthesis:
Tri-tert-butylphosphine tetrafluoroborate is used as a hindered phosphine salt with a Pd(0)-15-membered, triolefinic, macrocycle in Suzuki cross-coupling reactions of aryl bromides and chlorides. This application aids in the formation of substituted biaryl compounds, which are essential in the synthesis of various organic molecules.
Used in Dye-Sensitized Solar Cells:
Tri-tert-butylphosphonium tetrafluoroborate is used in the synthesis of a novel organic dye with a fluorenone conjugation bridge, which is employed in dye-sensitized solar cells to improve their efficiency and performance.
Used in Heck Coupling Reactions:
Tri-tert-butylphosphine tetrafluoroborate is utilized in the Heck coupling of non-activated vinyl tosylates with electron-deficient olefins, contributing to the synthesis of complex organic molecules and materials.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 131274-22-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,1,2,7 and 4 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 131274-22:
(8*1)+(7*3)+(6*1)+(5*2)+(4*7)+(3*4)+(2*2)+(1*2)=91
91 % 10 = 1
So 131274-22-1 is a valid CAS Registry Number.
InChI:InChI=1/C12H27P.BF4/c1-10(2,3)13(11(4,5)6)12(7,8)9;2-1(3,4)5/h1-9H3;/q;-1/p+1
131274-22-1Relevant articles and documents
Convenient preparation of tri-tert-butylphosphonium tetrafluoroborate
Saget, Tanguy,Cramer, Nicolai
, p. 2369 - 2371 (2011)
The versatile tri-tert-butylphosphonium tetrafluoroborate ligand is prepared in a convenient, simple, and high-yielding procedure without the isolation of sensitive intermediates. Georg Thieme Verlag Stuttgart New York.
Process for synthesizing tri-tert-butylphosphonium tetrafluoroborate
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Paragraph 0017; 0019-0020; 0022-0023; 0025-0026; ..., (2021/11/26)
A tert-butyl Grignard reagent is reacted with phosphorus trihalide and boron trifluoride, the reaction is finished, a hydrofluoric acid aqueous solution is added to form a salt, the layering is extracted, and the tri-tert-butylphosphonium - tetrafluoroborate is obtained through recrystallization. The method is simple, feasible, safe and environment-friendly. When the tert-butyl Grignard reagent is reacted with the phosphorus trihalide, the tert-butyl phosphorus intermediate acts in the reaction process by adding the boron trifluoride complex, thereby improving the halogen ion release property, improving the tri-substituted product to 94 - 95%, the reaction yield 85 - 87% and the organic solvent can be recycled.
Effect of side chain substituents on the electron injection abilities of unsymmetrical perylene diimide dyes
Dinalp, Haluk,Akar, Zuhal,Zafer, Ceylan,Li, Sddk
experimental part, p. 182 - 191 (2012/01/13)
Three near-infrared (NIR) absorbing unsymmetrical perylene diimide D-A-D type dyes containing 6-undecanoxy as donor group were utilized in dye-sensitized nanocrystalline TiO2 solar cells. Structure of the acceptor side of the molecules were improved by adding 4-[2-methyl-5-(cyanoacrylic acid)-3-thienyl]-phenyl (V), 3-carboxy-2-pyridil (VI) and 3-carboxy-2-pyrazyl (VII) moieties attached to one of the N-side of the dye. The relationship between the molecular structure of the acceptor sites of the dyes and the photovoltaic performances were discussed. Electrochemical measurements indicated that band gaps of the dyes were energetically favorable for electron injection from the excited state of the dyes to the conduction band of TiO2 nanoparticles. However, three dyes gave lower conversion efficiency on DSSC applications. Strong electron-withdrawing nature of perylene core might not permit to transfer the photo-generated electrons to the carboxyl groups anchoring to TiO2 surface, and then solar-to-electricity conversion efficiencies of the dyes were reduced.
