1179-05-1

Basic information

• Product Name: Phosphine, 1,3-phenylenebis[diphenyl-
• CAS NO: 1179-05-1
• Molecular Formula: C30H24P2
• Molecular Weight: 446.468
• Mol File: 1179-05-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Phosphine, 1,3-phenylenebis[diphenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphine, 1,3-phenylenebis[diphenyl-(1179-05-1)
• EPA Substance Registry System: Phosphine, 1,3-phenylenebis[diphenyl-(1179-05-1)

Safety Data

• Hazardous Substances Data: 1179-05-1(Hazardous Substances Data)

Usage

General Description

Phosphine, 1,3-phenylenebis[diphenyl-, commonly known as triphenylphosphine, is an organophosphorus compound that is critical in the realm of chemistry. This colorless crystalline material is soluble in organic solvents and is widely used on both laboratory and commercial scales in various chemical reactions. Its chemical formula is (C6H5)3P, indicating the presence of three phenyl rings attached to a phosphorus atom. It exudes a strong, unpleasant odor and should be handled with caution. Its applications involve usage in the synthesis of organic and inorganic compounds, acting as a ligand in metal complexes, and catalyzing a variety of organic reactions.

Upstream product

• 1257322-40-9 1,3-phenylene-bis(diphenylphosphine-borane) 
• 108-36-1 1,3-dibromobenzene 
• 1079-66-9 chloro-diphenylphosphine 
• 829-85-6 diphenylphosphane 
• 40841-62-1 (diphenylphosphino)(p-tolyl)methanone 
• 1448813-56-6 1,3-phenylenebis((diphenylphosphanyl)methanone) 

Downstream Products

• 138996-91-5 C₃₀H₂₆P₂ 
• 138996-90-4 C₃₀H₂₆P₂ 
• 138996-88-0 1,3-bis(phenylphosphino)benzene 
• 829-85-6 diphenylphosphane 
• 1415495-34-9 C₃₂H₂₈P₂ 
• 1415495-30-5 C₃₄H₂₈O₂P₂Rh⁽¹⁺⁾*CF₃O₃S^(1-) 

Relevant articles and documents

Mechanistically Guided One Pot Synthesis of Phosphine-Phosphite and Its Implication in Asymmetric Hydrogenation

Although hybrid bidentate ligands are known to yield highly enantioselective products in asymmetric hydrogenation (AH), synthesis of these ligands is an arduous process. Herein, a one pot, atom-economic synthesis of a hybrid phosphine-phosphite (L1) is reported. After understanding the reactivity difference between an O-nucleophile versus C-nucleophile, one pot synthesis of Senphos (L1) was achieved (72 %). When L1 was treated with [Rh], 31P NMR revealed bidentate coordination to Rh. Senphos, in the presence of rhodium, catalyzes the AH of Methyl-2-acetamido-3-phenylacrylate and discloses an unprecedented turn over frequency of 2289, along with excellent enantio-selectivity (92 %). The generality is demonstrated by hydrogenating an array of alkenes. The AH operates under mild conditions of 1–2 bar H2 pressure, at room temperature. The practical relevance of L1 is demonstrated by scaling-up the reaction to 1 g and by synthesizing DOPA, a drug widely employed for the treatment of Parkinson's disease. Computational insights indicate that the R isomer is preferred by 3.8 kcal/mol over the S isomer.

Differentially Substituted Phosphines via Decarbonylation of Acylphosphines

A new route to phosphines was developed by a method that features a "pre-join and transform" process that proceeds via acylphosphine intermediates that may be readily prepared from carboxylic acids and disubstituted phosphines. The efficient decarbonylations of these acylphosphines using a nickel catalyst delivered the corresponding phosphines. This method shows that the carboxyl group can play a role similar to halides or triflates for introducing a substituted phosphorus atom on an aromatic ring.