13716-12-6 Usage
Description
Tri-tert-butylphosphine is a colorless to light yellow liquid that is primarily used in the preparation of monoand bidentate phosphine ligands in metal complexes. These ligands are essential for catalytic chiral asymmetric hydrogenations, other asymmetric reactions, and transition metal coupling reactions. Additionally, this reagent is utilized in the synthesis of other phosphines for catalytic polymerization reactions.
Uses
Used in Chemical Synthesis:
Tri-tert-butylphosphine is used as a valuable ligand for several coupling reactions in the chemical synthesis industry. Its role in the preparation of phosphine ligands for metal complexes makes it a crucial component in the production of various chemical compounds.
Used in Catalytic Asymmetric Hydrogenations:
In the field of asymmetric hydrogenations, Tri-tert-butylphosphine is used as a ligand for metal complexes, enabling the selective formation of chiral products with high enantioselectivity and efficiency.
Used in Asymmetric Reactions:
Tri-tert-butylphosphine is employed as a ligand in various asymmetric reactions, contributing to the development of enantiomerically pure compounds, which are essential in the pharmaceutical and agrochemical industries.
Used in Transition Metal Coupling Reactions:
This reagent is used as a ligand in transition metal coupling reactions, facilitating the formation of carbon-carbon and carbon-heteroatom bonds, which are vital in the synthesis of complex organic molecules.
Used in Catalytic Polymerization:
Tri-tert-butylphosphine is used in the preparation of other phosphines that act as catalysts in polymerization reactions, leading to the production of various polymers with specific properties and applications.
Used in Convenient Handling:
The product is offered as a THF (tetrahydrofuran) solution, which provides more convenient handling and improved safety during the synthesis process. This form of the reagent is particularly useful in research and development settings, as well as in industrial applications where ease of use and safety are paramount.
Reaction
Useful as a ligand in a variety of palladium-catalyzed C-N, C-O and C-C bond-forming reactions under mild conditions.
Check Digit Verification of cas no
The CAS Registry Mumber 13716-12-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,7,1 and 6 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 13716-12:
(7*1)+(6*3)+(5*7)+(4*1)+(3*6)+(2*1)+(1*2)=86
86 % 10 = 6
So 13716-12-6 is a valid CAS Registry Number.
InChI:InChI=1/C12H27P/c1-10(2,3)13(11(4,5)6)12(7,8)9/h1-9H3
13716-12-6Relevant articles and documents
Reactivity of [Pt(PtBu3)2] with Zinc(I/II) Compounds: Bimetallic Adducts, Zn-Zn Bond Cleavage, and Cooperative Reactivity
Hidalgo, Nereida,Romero-Pérez, Carlos,Maya, Celia,Fernández, Israel,Campos, Jesús
, p. 1113 - 1119 (2021)
Metal-only Lewis pairs (MOLPs) based on zinc electrophiles are particularly interesting due to their relevance to Negishi cross-coupling reactions. Zinc-based ligands in bimetallic complexes also render unique reactivity to the transition metals at which
Oxidative ring expansion of a low-coordinate palladacycle: Synthesis of a robust T-shaped alkylpalladium(II) complex
Sinclair, Matthew J.G.,Chaplin, Adrian B.
, (2020)
The synthesis of an unusual T-shaped alkylpalladium(II) complex featuring a cyclometalated tri-tert-butylphosphineoxide ligand by oxidation of the corresponding cyclometalated tri-tert-butylphosphine complex with PhIO is reported. We speculate that this reaction proceeds by formation of a transient palladium oxo intermediate and there are structural similarities with a late transition metal exemplar: Milstein's seminal pincer ligated Pt(IV) oxo (Nature 2008, 455, 1093–1096).
Process for synthesizing tri-tert-butylphosphonium tetrafluoroborate
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Paragraph 0017-0018; 0020-0021; 0023-0024; 0026-0027; ..., (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.