149968-36-5

Basic information

• Product Name: 1,3-BIS(DI-T-BUTYLPHOSPHINOMETHYL)BENZENE
• Synonyms: 1,3-BIS(DI-T-BUTYLPHOSPHINOMETHYL)BENZENE;1,3-BIS(DI-TERT-BUTYLPHOSPHINOMETHYL)BENZENE;1,3-Bis(di-t-butylphosphinomethyl)benzene,99%;1,3-Bis(di-tert-butylphosphinomethyl)benzene 97%;ditert-butyl-[[3-(ditert-butylphosphanylmethyl)phenyl]methyl]phosphane
• CAS NO: 149968-36-5
• Molecular Formula: C₂₄H₄₄P₂
• Molecular Weight: 394.55
• Product Categories: organophosphine ligand;Achiral Phosphine;Aryl Phosphine
• Mol File: 149968-36-5.mol

Chemical Properties

• Melting Point: 68-75°C
• Boiling Point: 459.3±38.0 °C(Predicted)
• Appearance: white/Powder
• Sensitive: air sensitive
• CAS DataBase Reference: 1,3-BIS(DI-T-BUTYLPHOSPHINOMETHYL)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BIS(DI-T-BUTYLPHOSPHINOMETHYL)BENZENE(149968-36-5)
• EPA Substance Registry System: 1,3-BIS(DI-T-BUTYLPHOSPHINOMETHYL)BENZENE(149968-36-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 149968-36-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
1,3-BIS(DI-T-BUTYLPHOSPHINOMETHYL)BENZENE is used as a phosphine ligand in the synthesis of pharmaceuticals for its ability to form stable complexes with transition metals, facilitating various catalytic processes that are essential in the production of medicinal compounds.
Used in Agrochemical Production:
In the agrochemical industry, 1,3-BIS(DI-T-BUTYLPHOSPHINOMETHYL)BENZENE is utilized as a ligand in transition metal catalysis to enhance the efficiency of reactions involved in the synthesis of agrochemicals, contributing to the development of effective and targeted pesticides and fertilizers.
Used in Advanced Material Synthesis:
1,3-BIS(DI-T-BUTYLPHOSPHINOMETHYL)BENZENE is employed as a key component in the synthesis of advanced materials, where its role as a phosphine ligand in metal catalysis aids in the creation of materials with specific properties required for high-tech applications.
Used in Transition Metal Catalysis:
1,3-BIS(DI-T-BUTYLPHOSPHINOMETHYL)BENZENE is used as a ligand in transition metal catalysis for its chelating ability and steric protection, which are crucial for enhancing the selectivity and efficiency of various catalytic processes, including coupling reactions and hydrogenation reactions.

Upstream product

• 415707-44-7 ((C₄H₉)2PCH₂)2C₆H₃PtH₂⁽¹⁺⁾*CF₃SO₃^(1-)=((C₄H₉)2PCH₂)2C₆H₃PtH₂CF₃SO₃ 
• 1333-74-0 hydrogen 
• 415707-43-6 ((C₄H₉)2PCH₂)2C₆H₃PtClC⁽²⁾H₂Cl⁽¹⁺⁾*B((CF₃)2C₆H₃)4^(1-)=((C₄H₉)2PCH₂)2C₆H₃PtClC⁽²⁾H₂ClB((CF₃)2C₆H₃)4 
• 13716-10-4 di(tert-butyl)chlorophosphine 
• 626-15-3 1,3-bis-(bromomethyl)benzene 

Downstream Products

• 675623-70-8 m-C₆H₄(CH₂(t-Bu)2PNH)2 
• 1087244-23-2 [RuCl(C₆H₃(CH₂P(C(CH₃)3)2)2)(P(C₆H₅)3)] 
• 86365-89-1 [(C₆H₃(CH₂P(C(CH₃)3)2)(CH₂P(C(CH₃)3)(C(CH₃)2CH₂)))RhH] 
• 866367-20-6 (2,6-bis[(di-tert-butylphosphino)methyl]phenyl)PdPh 

Relevant articles and documents

One-Pot Synthesis of 1,3-Bis(phosphinomethyl)arene PCP/PNP Pincer Ligands and Their Nickel Complexes

A one-pot synthesis of arene-based PCP/PNP ligands has been developed. The reaction of 1,3-bis(bromomethyl)benzene or 2,6-bis(bromomethyl)pyridine with various chlorophosphines in acetonitrile afforded bis-phosphonium salts. These salts can then be reduced by magnesium powder to yield PCP or PNP ligands. In comparison to traditional synthetic methods for making PCP/PNP ligands involving the use of secondary phosphines, this new alternative method allows for the use of chlorophosphines, which are cheaper, safer to handle, and have a broader range of commercially available derivatives. This is especially true for the chlorophosphines with less bulky alkyl groups. Moreover, the one-pot procedure can be extended to allow for the direct synthesis of PCP/PNP nickel complexes. By using nickel powder as the reductant, the resulting nickel halide was found to directly undergo metalation with the PCP or PNP ligand to generate nickel complexes in high yields.

Practical Gas Cylinder-Free Preparations of Important Transition Metal-Based Precatalysts Requiring Gaseous Reagents

A simple and safe setup for the synthesis of a selection of important transition metal-based precatalysts is reported, all requiring low-molecular weight gaseous reagents for their preparation. Hydrogen, carbon monoxide, ethylene, and acetylene are each liberated in a controlled manner from a corresponding easy-to-handle precursor in a closed two-chamber reactor. Gas cylinders and elaborate setups/techniques connected to handling toxic and/or flammable gases as reported in the literature can thus be avoided. The corresponding precatalysts are of high relevance in the active research fields of C-H bond activation, dehydrogenation, hydrogenation, and coupling reactions. The selection of complexes shown is meant to serve as examples for the usefulness and broadness of the presented methods, allowing precatalysts requiring gaseous reagents to become available for the research community.

Protonation of (PCP)PtH to give a dihydrogen complex

The protonation of (PCP)PtH (PCP=η3-2,6-(tBu2PCH2) 2C6H3) to give a (PCP)PtII dihydrogen complex was reported. The reaction was accomplished in CD2Cl2 with [H(OEt2)2]+BAr′4- [Ar′ = 3,5-bis(trifluoromethyl)phenyl]. The analysis showed that the H2 ligand was expelled when the solution was warmed to room temperature, but the dihydrogen complex was reformed when H2 was added.