597-50-2

Basic information

• Product Name: TRIETHYLPHOSPHINE OXIDE
• Synonyms: (C2H5)3P=O;(Diethyl-phosphinoyl)-ethane;ai3-51002;nsc41934;Phosphine oxide, triethyl-;skf39804;tl433;Triethylphoshorus oxide
• CAS NO: 597-50-2
• Molecular Formula: C₆H₁₅OP
• Molecular Weight: 134.16
• Product Categories: Phosphine Oxides and Sulfides;Catalysis and Inorganic Chemistry;Phosphine Ligands;Phosphorus Compounds;organophosphorus compound
• Mol File: 597-50-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: 48-52 °C(lit.)
• Boiling Point: 84-85 °C (3 mmHg)
• Flash Point: 133 °F
• Appearance: White/Needles
• Density: 0.884
• Vapor Pressure: 0.0512mmHg at 25°C
• Refractive Index: 1.399
• Water Solubility: Soluble in water.
• Stability: hygroscopic
• CAS DataBase Reference: TRIETHYLPHOSPHINE OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIETHYLPHOSPHINE OXIDE(597-50-2)
• EPA Substance Registry System: TRIETHYLPHOSPHINE OXIDE(597-50-2)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 45-36/37/39-26
• RIDADR: 1759
• WGK Germany: 3
• RTECS: SZ1640000
• Hazardous Substances Data: 597-50-2(Hazardous Substances Data)

Usage

Chemical Properties

White needles

Uses

Triethylphosphine oxide is used as a probe molecule and systems are evaluated by 31P NMR spectroscopy. Triethylphosphine oxide is used to produce tris(perfluoroethyl)difluorophosphane. This reaction will need reagent of HF. This reaction needs electrochemical fluorination.

InChI:InChI=1/C6H15OP/c1-4-8(7,5-2)6-3/h4-6H2,1-3H3

Upstream product

• 75-15-0 carbon disulfide 
• 28860-45-9 triethyl-benzoylimino-phosphorane 
• 64-17-5 ethanol 
• 24952-49-6 triethyl-phenylimino-phosphorane 
• 861373-39-9 fluoren-9-ylidene-triethylphosphoranylidene-hydrazine 
• 141-52-6 sodium ethanolate 
• 15719-64-9 methylammonium carbonate 
• 4896-89-3 tetraethyl-phosphonium; ethylate 
• 27063-22-5 tetraethylphosphonium; tetraethylphosphonium acetate 
• 525-06-4 diphenyl ketene 
• 71-43-2 benzene 
• 108-88-3 toluene 
• 958-80-5 bis(4-methoxyphenyl)thione 
• 554-70-1 triethylphosphine 

Downstream Products

• 554-70-1 triethylphosphine 
• 850255-93-5 (C₂H₅)3POB(OC₆H₅)3 
• 356074-05-0 (Ph₃PO)B(C₆F₅)3 
• 1013-23-6 Dibenzothiophene sulfoxide 
• 1638261-73-0 C₂₄BF₂₀^(1-)*C₆H₁₅FP⁽¹⁺⁾ 
• 1356584-33-2 C₆F₄B(C₆F₅)(OP(C₂H₅)3)CH₂P(C(CH₃)3)2⁽¹⁺⁾*SO₃CF₃^(1-)=[C₆F₄B(C₆F₅)(OP(C₂H₅)3)CH₂P(C(CH₃)3)2](SO₃CF₃) 

Relevant articles and documents

Lewis Acidic Boranes, Lewis Bases, and Equilibrium Constants: A Reliable Scaffold for a Quantitative Lewis Acidity/Basicity Scale

A quantitative Lewis acidity/basicity scale toward boron-centered Lewis acids has been developed based on a set of 90 experimental equilibrium constants for the reactions of triarylboranes with various O-, N-, S-, and P-centered Lewis bases in dichloromethane at 20 °C. Analysis with the linear free energy relationship log KB=LAB+LBB allows equilibrium constants, KB, to be calculated for any type of borane/Lewis base combination through the sum of two descriptors, one for Lewis acidity (LAB) and one for Lewis basicity (LBB). The resulting Lewis acidity/basicity scale is independent of fixed reference acids/bases and valid for various types of trivalent boron-centered Lewis acids. It is demonstrated that the newly developed Lewis acidity/basicity scale is easily extendable through linear relationships with quantum-chemically calculated or common physical–organic descriptors and known thermodynamic data (ΔH (Formula presented.)). Furthermore, this experimental platform can be utilized for the rational development of borane-catalyzed reactions.

Reactivity of auranofin with selenols and thiols - Implications for the anticancer activity of gold(I) compounds

The enzyme thioredoxin reductase (TrxR) is attracting much interest as a potential target for cancer therapy. The presence of a selenium atom in the catalytic site makes it sensitive to inhibition by electrophilic molecules, including the AuI complex auranofin [2,3,4,6-tetra-O-acetyl-1-thio- β-D-glucopyranosato-S-(triethylphosphane)gold]. The reactions between auranofin and models of thiol and selenol nucleophiles present in TrxR (PhSH and PhSeH) have been investigated in chloroform and methanol by means of 1H, 31P, and 77Se NMR spectroscopy. In chloroform, auranofin undergoes ligand substitution of the tetraacetylthioglucose moiety by a PhS or PhSe group. The reaction is reversible in both cases, but it is characterized by widely different equilibrium constants (ca. 1 for S and at least 103 for Se). In polar solvents, such as methanol, the reaction is more complex, and the phosphane moiety also undergoes ligand exchange. Some features have been clarified through the investigation of Et3PAuCl. The elementary processes involved have been characterized by DFT calculations. Copyright

Reactions of elemental phosphorus and phosphines with electrophiles in superbasic systems: XII. Synthesis of unsymmetrical tertiary phosphine oxides from red phosphorus and organyl halides

Alkyldibenzyl- and benzyldialkylphosphine oxides were prepared in one stage by direct phosphorylation of a mixture of alkyl bromides and benzyl chloride with red phosphorus under the conditions of phase-transfer catalysis (concentrated aqueous KOH solution-dioxane-benzyltriethylammonium chloride).