107783-62-0

Basic information

• Product Name: 1,2-Bis(di-tert-butylphosphino)ethane
• Synonyms: 2-(tert-butyl(2-(di-tert-butylphosphino)ethyl)phosphino)-2-methylpropane;1,2-BIS(DI-TERT-BUTYLPHOSPHINO)ETHANE
• CAS NO: 107783-62-0
• Molecular Formula: C18H40P2
• Molecular Weight: 318.46
• Mol File: 107783-62-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 361.2±25.0 °C(Predicted)
• Appearance: /
• CAS DataBase Reference: 1,2-Bis(di-tert-butylphosphino)ethane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Bis(di-tert-butylphosphino)ethane(107783-62-0)
• EPA Substance Registry System: 1,2-Bis(di-tert-butylphosphino)ethane(107783-62-0)

Safety Data

• Hazardous Substances Data: 107783-62-0(Hazardous Substances Data)

Usage

Description

1,2-Bis(di-tert-butylphosphino)ethane, commonly known as dtbpe or BPE, is a bidentate ligand characterized by its central ethane backbone with two di-tert-butylphosphino (dtbpe) groups attached to the terminal carbon atoms. The bulky and electron-rich phosphine groups of BPE offer steric and electronic protection to metal centers, which is instrumental in stabilizing and activating a diverse array of metal complexes. Its versatile coordination properties and unique steric effects render BPE an indispensable tool in the advancement of various catalytic processes.

Uses

Used in Coordination Chemistry:
1,2-Bis(di-tert-butylphosphino)ethane is used as a bidentate ligand for providing steric and electronic protection to metal centers, which is crucial for stabilizing metal complexes in coordination chemistry.
Used in Catalysis:
1,2-Bis(di-tert-butylphosphino)ethane is used as a ligand in catalytic processes for its ability to stabilize and activate metal complexes, thereby enhancing the efficiency of reactions such as asymmetric hydrogenation, cross-coupling reactions, and C-H activation.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
1,2-Bis(di-tert-butylphosphino)ethane is used as a chiral auxiliary to induce asymmetry in chemical reactions, which is vital for the synthesis of enantiomerically pure compounds, a key aspect in the production of pharmaceuticals and agrochemicals.
Used as a Stabilizer in Nanoparticle Synthesis:
1,2-Bis(di-tert-butylphosphino)ethane is used as a stabilizer in the synthesis of nanoparticles to control their size, shape, and dispersity, which is essential for their performance in various applications, including catalysis, electronics, and medicine.

Upstream product

• 69441-93-6 1,2-bis(di-tert-butylphosphoryl)ethane 
• 74-85-1 ethene 
• 28240-69-9 1,2-bis(dichlorophosphino)ethane 
• 594-19-4 tert.-butyl lithium 

Downstream Products

• 1196998-25-0 [(1,2-bis(di-tert-butylphosphino)ethane)Pt(η2-PhCCCF3)] 
• 1196998-28-3 [(1,2-bis(di-tert-butylphosphino)ethane)Pt(η2-PhCCC(CH3)3)] 
• 1438463-42-3 [(1,2-bis(di-tert-butylphosphino)ethane)Ni(CH₃CH₂COO)]BArF 

Related news

Synthesis of 1,2-bis(di-tert-butylphosphino)ethane (dtbpe) complexes of nickel: radical coupling and reduction reactions promoted by the nickel(I) dimer [(dtbpe)NiCl]208/16/2019

Tetrahydrofuran solutions of (dtbpe)NiCl2 (dtbpe=1,2-bis(di-tert-butylphosphino)ethane) are reduced by KC8 to afford the dimeric Ni(I) complex [(dtbpe)NiCl]2 (1) in 73% yield. Reaction of 1 with [FeCp2][PF6] effects a one-electron oxidation to give the mixed-valent Ni(I,II) binuclear species [{(...detailed

Relevant articles and documents

A convenient synthetic protocol to 1,2-bis(dialkylphosphino)-ethanes

1,2-Bis(dialkylphosphino)ethanes are readily prepared from the parent phosphine oxides, via a novel sodium aluminium hydride/sodium hydride reduction protocol of intermediate chlorophosphonium chlorides. This approach is amenable to multi-gram syntheses, utilises readily available and inexpensive reagents, and benefits from a facile non-aqueous work-up in the final reductive step.

Bis(di-tert-butylphosphino)ethane-nickel(0) Complexes

Ni(cdt) reacts with tBu2PC2H4PtBu2 in pentane at 20 deg C to yield brownish crystals of (tBu2PC2H4PtBu2)Ni(η2-C12H18) (1).The molecular structure of 1, as established by X-ray crystallography, exhibits a trigonal-planar coordination geometry of the nickel center with a η2-bonded cdt ligand.In the crystal 1 exists as two enantiomers, which are determined by the left- or right-handed screw axis of the cdt ligand.The cdt ligand in 1 resists most typical displacement reactions but 1 reacts with CO at -78 deg C to afford the colorless 18e complex (tBu2PC2H4PtBu2)Ni(CO)2 (2).From the reaction of Ni(cod)2 with tBu2PC2H4PtBu2 yellow needles of (tBu2PC2H4PtBu2)Ni(η2-cod) (3) are obtained.Low temperature NMR spectroscopy established that only one diene C=C bond is coordinated to nickel(0).At higher temperatures a rapid exchange of the coordinated and unbound C=C bonds is induced.When solutions of 3 are kept at 20 deg C for several days the dinuclear, almost insoluble yellow complex tBu2PC2H4PtBu2)Ni>2(μ-η2,η2-cod) (4) precipitates.The reaction of Ni(C2H4)3 and tBu2PC2H4PtBu2 affords orange (tBu2PC2H4PtBu2)Ni(C2H4) (5).From Ni(1,5-hexadiene)2 and tBu2PC2H4PtBu2 in 1,5-hexadiene the yellow-greenish complex (tBu2PC2H4PtBu2)Ni(η2-C6H10) (6) is obtained.As for 3, only one diene C=C bond is coordinated to nickel(0), but the structure is fluxional with exchange of the coordinated and unbound C=C bonds (NMR at 20 degC).From a solution of 6 in pentane the dinuclear, diastereomeric compounds rac/meso-tBu2PC2H4PtBu2)Ni>2(μ-η2,η2-C6H10) (7a,b) separate in large yellow crystals.In similar reactions the 1,6-heptadiene complexes (tBu2PC2H4PtBu2)Ni(η2-C7H12) (8) and rac/meso-tBu2PC2H4PtBu2)Ni>2(μ-η2,η2-C7H12) (9a,b) are also obtained.In 6, 7a,b, 8, and 9a,b the open-chain diene ligands can easily be displaced, e.g., by ethene to afford 5.Thus, complexes 6, 7a,b, 8, 9a,b are the most reactive.These complexes react readily (the ethene derivative 5 also reacts but very slowly) with butadiene to yield large yellow cubes of (tBu2PC2H4PtBu2)Ni(η2-C4H6) (10), which is also fluxional.The alkene complexes 5, 6, 7a,b, 8, 9a,b, 10 react with ethyne to yield yellow-brownish crystalline (tBu2PC2H4PtBu2)Ni(C2H2) (11).Key Words: Alkenens, Ethyne, Nickel(0), Phosphane, X-Ray