5518-62-7

Usage

Uses

It is used in chemical research organic Intermediates.

InChI:InChI=1/C2H8P2/c3-1-2-4/h1-4H2

Upstream product

• 995-32-4 tetraethyl ethylenebis(phosphonate) 
• 28240-69-9 1,2-bis(dichlorophosphino)ethane 

Downstream Products

• 136779-26-5 1,2-bis((2S,5S)-2,5-dimethylphospholano)ethane 
• 136779-27-6 (S)-Et-BPE 
• 136705-63-0 1,2-bis((2R,5R)-2,5-diisopropylphospholano)ethane 
• 136705-62-9 (+)-1,2-bis((2R,5R)-2,5-diethylphospholano)ethane 
• 437606-60-5 1,2-bis((1S,2R)-2-benzylphospholano)ethane 
• 28240-69-9 1,2-bis(dichlorophosphino)ethane 
• 127502-06-1 Tetrofosmin 
• 251459-19-5 1,2-bis[(2R,5R)-2,5-benzyloxymethylphospholanyl]ethane 

Relevant academic research and scientific papers

In vitro antitumor activity of the water soluble copper(I) complexes bearing the tris(hydroxymethyl)phosphine ligand

Monocationic hydrophilic complexes [Cu(thp)4]+ 3 and [Cu(bhpe)2]+ 4 were synthesized by ligand exchange reactions starting from the labile [Cu(CH3CN)4][PF 6] precursor in the presence of an excess of the relevant hydrophilic phosphine. Complexes 3 and 4 were tested against a panel of several human tumor cell lines. Complex 3 has been shown to be about 1 order of magnitude more cytotoxic than cisplatin. Chemosensitivity tests performed on cisplatin and multidrug resistance phenotypes suggested that complex 3 acts via a different mechanism of action than the reference drug. Different short-term proliferation assays suggested that lysosomal damage is an early cellular event associated with complex 3 cytotoxicity, probably mediated by an increased production of reactive oxygen species. Cytological stains and flow cytometric analyses indicated that the phosphine copper(I) complex is able to inhibit the growth of tumor cells via G2/M cell cycle arrest and paraptosis accompanied with the loss of mitochondrial transmembrane potential.

A Universally Applicable Methodology for the Gram-Scale Synthesis of Primary, Secondary, and Tertiary Phosphines

Although organophosphine syntheses have been known for the better part of a century, the synthesis of phosphines still represents an arduous task for even veteran synthetic chemists. Phosphines as a class of compounds vary greatly in their air sensitivity, and the misconception that it is trivial or even easy for a novice chemist to attempt a seemingly straightforward synthesis can have disastrous results. To simplify the task, we have previously developed a methodology that uses benchtop intermediates to access a wide variety of phosphine oxides (an immediate precursor to phosphines). This synthetic approach saves the air-free handling until the last step (reduction to and isolation of the phosphine). Presented herein is a complete general procedure for the facile reduction of phosphonates, phosphinates, and phosphine oxides to primary, secondary, and tertiary phosphines using aluminum hydride reducing agents. The electrophilic reducing agents (iBu)2AlH and AlH3 were determined to be vastly superior to LiAlH4 for reduction selectivity and reactivity. Notably, it was determined that AlH3 is capable of reducing the exceptionally resistant tricyclohexylphosphine oxide, even though LiAlH4 and (iBu)2AlH were not. Using this new procedure, gram-scale reactions to synthesize a representative range of primary, secondary, and tertiary phosphines (including volatile phosphines) were achieved reproducibly with excellent yields and unmatched purity without the need for a purification step.

Backbone-Modified Bisdiazaphospholanes for Regioselective Rhodium-Catalyzed Hydroformylation of Alkenes

A series of tetraaryl bisdiazaphospholane (BDP) ligands were prepared varying the phosphine bridge, backbone, and substituents in the 2- and 5-positions of the diazaphospholane ring. The parent acylhydrazine backbone was transformed to an alkylhydrazine via a borane reduction procedure. These reduced ligands contained an all sp3 hybridized ring mimicking the all sp3 phospholane of (R,R)-Ph-BPE, a highly selective ligand in asymmetric hydroformylation. The reduced bisdiazaphospholane (red-BDP) ligands were shown crystallographically to have an increased C-N-N-C torsion angle - this puckering resembles the structure of (R,R)-Ph-BPE and has a dramatic influence on regioselectivity in rhodium catalyzed hydroformylation. The red-BDPs demonstrated up to a 5-fold increase in selectivity for the branched aldehyde compared to the acylhydrazine parent ligands. This work demonstrates a facile procedure for increased branched selectivity from the highly active and accessible class of BDP ligands in hydroformylation.

Organophosphines

Organophosphines of the formula (R)aP(H)3?a( where R is C1-C20 alkyl, alkenyl, alkaryl or styryl and a is 1, 2, or 3) are produced by (i) reacting a tris(hydroxyorgano)phosphine (THP) with an organic halogen containing compound; (ii) reacting the product of (i) with a base; (iii) removing aldehydes from the product of (ii) and adding an organic phase, followed by distillation or phase-separation to obtain the desired product.