Triphenylphosphine oxide

• CAS: 791-28-6
• Catalog Number: ACM791286-3
• Category: Main Products
• Molecular Weight: 278.28
• Molecular Formula: C18H15OP
• Synonyms: Phosphine oxide, triphenyl-; Triphenyl phosphorus oxide; (C6H5)3P=O; Triphenylphosphanoxid; Triphenylphosphanoxide; (C6H5)3PO;Triphenylphosphine oxide;Triphenyl phosphorus oxide
• IUPAC Name: diphenylphosphorylbenzene
• Canonical SMILES: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)C3=CC=CC=C3
• InChI: 1S/C18H15OP/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
• InChI Key: FIQMHBFVRAXMOP-UHFFFAOYSA-N
• Boiling Point: 360 °C
• Melting Point: 150-157 °C(lit.)
• Flash Point: 180 °C
• Density: 1.212 g/cm3
• Appearance: Solid
• Application: Flame Retardant
• Storage: Store at RT.
• Complexity: 281
• Covalently-Bonded Unit Count: 1
• EC Number: 212-338-8
• Exact Mass: 278.086g/mol
• H-Bond Acceptor: 1
• Heavy Atom Count: 20
• Isomeric SMILES: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)C3=CC=CC=C3
• Monoisotopic Mass: 278.086g/mol
• Notes: Triphenylphosphine Oxide uses and applications include: Flame retardant; vapor-phase flame inhibitor
• NSC Number: 398
• Octanol Water Partition Coefficient: 2.83 (LogP)
• Physical Description: DryPowder
• Physical State: Solid
• Rotatable Bond Count: 3
• Topological Polar Surface Area: 17.1A^2
• UNII: Z69161FKI3
• Vapor Pressure: 2.60e-09 mmHg

Case Study

Triphenylphosphine oxide as a crystallization aid

Etter, Margaret C., and Paul W. Baures.Journal of the American Chemical Society 110.2 (1988): 639-640.

Triphenylphosphine oxide (TPPO) is a good proton acceptor and is known to form complexes with a wide variety of organic molecules in solution. These complexes are stabilized by strong hydrogen bonds between the phosphate oxygen and the substrate proton donor. Cocrystallization with TPPO induces many organic compounds to crystallize readily as bulky crystals with sharp edges and well-defined crystal faces. TPPO itself readily forms high-quality crystals, a property carried over to its complexes. For organic compounds that form poor-quality crystals or are only available in small quantities, TPPO complexation is a new approach to convert these compounds into useful crystals.
TPPO complexes of the compounds listed in Figure I were prepared by dissolving equimolar amounts of substrate and triphenylphosphine oxide (TPPO) in toluene and then allowing the solution to evaporate slowly at room temperature. Crystals were removed from solution as they formed, washed quickly with acetone and petroleum ether, and then air-dried. The crystals were confirmed to be TPPO complexes by various techniques. Each batch of crystals was examined under a polarizing microscope to determine whether the crystals had a uniform morphology or if a mixture of crystals was present.

Electroreduction of triphenylphosphine oxide to triphenylphosphine

Manabe, Shuhei, Curt M. Wong, and Christo S. Sevov. Journal of the American Chemical Society 142.6 (2020): 3024-3031.

The direct and scalable electroreduction of triphenylphosphine oxide (TPPO) to triphenylphosphine (Tpp) remains an unsolved challenge that would significantly reduce the cost and waste generated by large-scale performance of the desirable reaction mediated by Tpp. An electrochemical method is presented for the single-step reduction of TPPO to TPP using an aluminum anode in combination with a supporting electrolyte to continuously regenerate Lewis acid from the anodic oxidation product. The generated Lewis acid activates TPPO for reduction at mild potentials and promotes P-0 rather than P-C bond cleavage, resulting in the selective formation of TPP over other byproducts. Finally, this robust method is applied to the reduction of synthetically useful classes of phosphine oxides.
This robust method is evaluated for the synthesis of TPP on a multi-gram scale with minimal solvent and electrolyte waste from concentrated solutions. The solubility limit of TPPO is 250 mM. Despite limited solubility, the electrolysis was performed in a solution saturated with TPPO that contained enough solid TPPO to form a 0.5 M solution if dissolved, with solid TPPO continually dissolving as solvated TPPO was consumed during the electrolysis. Although the yield of TPP was high (72%), the selectivity for this desired product relative to DPPO was only 9:1. The reaction could now be run at loadings of 1 mmol TPPO per mL of solution (pseudo 1 M concentration).

Mechanistic study of decomposition of H2O2 by triphenylphosphine oxide

Tsuneda, Takao, Junpei Miyake, and Kenji Miyatake. ACS omega 3.1 (2018): 259-265.

The mechanism of decomposition of H2O2 by triphenylphosphine oxide (TPPO) was studied. TPPO is usually added as a component to proton exchange membrane electrolytes to inhibit membrane degradation caused by H2O2. But how TPPO reduces the concentration of free H2O2 in the membrane is unclear. According to the experimental X-ray structure, a TPPO dimer that captures two H2O2 molecules was used as a computational model. Vibrational spectra calculations of different hydration numbers showed that the model correctly reproduced the spectral peaks of TPPO capturing H2O2. Based on this model, the mechanism of decomposition of H2O2 by TPPO dimer was studied.
The geometry of the TPPO dimer + 2H2O2 model was optimized by changing the bond distances that affect each reaction step: the O-H bond distance of H2O2 (step 1), the P=O bond distance (step 2), and the bridging O-O bond distance (step 3). The program suite has been used to perform all LC-BLYP calculations. All optimized structures have been checked to ensure that they produce positive real frequencies. Transition state calculations were performed by the quadratic synchronous transformation method. The predictor-corrector integration method was used to calculate the intrinsic reaction coordinates (IRC) of the reaction. The vibrational modes affecting the IR spectra and their assignments were analyzed.

Studies on complexes of triphenylphosphine oxide with lanthanide bromides

Bowden, Allen, et al. Inorganica Chimica Acta 363.1 (2010): 243-249.

The reaction of hydrated lanthanide bromides and triphenylphosphine oxide in ethanol in ratios of 1:3 and 1:4 affords a series of complexes [LnBr2(Ph3PO)4]Br (Ln = Pr, Nd, Gd, Tb, Er, Yb, Lu) containing ethanol and water in the crystal lattice, regardless of the ratio of the reactants used. The single crystal X-ray structures of [NdBr2(Ph3PO)4]Br, [GdBr2(Ph3PO)4]Br, and [YbBr2(Ph3PO)4]Br have been determined and have octahedral geometry about the metal ions.
Mixture of hot ethanolic solutions of hydrated lanthanide bromides and triphenylphosphine oxide in ratios of 1:3 and 1:4 and slow cooling of the resulting solution overnight results in spontaneous formation of crystals suitable for single crystal X-ray analysis for most lanthanides. The same type of complexes are obtained regardless of the ratio of the reactants used. This is in contrast to the behavior of lanthanide chlorides with triphenylphosphine oxide, where both 1:3 and 1:4 complexes could be isolated. The sole formation of the tetrayl complex observed here could be due to solubility properties of the bromide compared with the chloride or to steric effects.

Custom Q&A

Is Triphenylphosphine oxide listed on Wikipedia?

Yes, Triphenylphosphine oxide is listed on Wikipedia under the page title "Triphenylphosphine_oxide".

What is the CAS number of Triphenylphosphine oxide?

The CAS number of Triphenylphosphine oxide is 791-28-6.

What is the Canonical SMILES of Triphenylphosphine oxide?

The Canonical SMILES of Triphenylphosphine oxide is C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)C3=CC=CC=C3.

How many heavy atoms does Triphenylphosphine oxide contain?

Triphenylphosphine oxide contains 20 heavy atoms.

Does Triphenylphosphine oxide have any hydrogen bond donor count?

Triphenylphosphine oxide does not have any hydrogen bond donor count.

What is the XLogP3 value of Triphenylphosphine oxide?

The XLogP3 value of Triphenylphosphine oxide is 2.8.

What are some synonyms for Triphenylphosphine oxide?

Some synonyms for Triphenylphosphine oxide include Phosphine oxide, triphenyl-, Triphenyl phosphorus oxide, and Triphenylphosphineoxide.

What is the molecular weight of Triphenylphosphine oxide?

The molecular weight of Triphenylphosphine oxide is 278.3g/mol.

Can you provide the InChIKey of Triphenylphosphine oxide?

The InChIKey of Triphenylphosphine oxide is FIQMHBFVRAXMOP-UHFFFAOYSA-N.