| Identification | More | [Name]
Triphenylphosphine oxide | [CAS]
791-28-6 | [Synonyms]
AURORA KA-1603
TPO
TRIPHENYLPHOSPHINE OXIDE
(C6H5)3P=O
Phosphine oxide, triphenyl-
Triphenyl phosphorus oxide
Triphenylphosphanoxid
Triphenylphosphanoxide
triphenyl-phosphineoxid
triphenylphosphorusoxide
TriphenylphosphineOxide,>98%
Triphenylphosphineoxide,99%
TPPO: Triphenylphosphine Oxide
Triphenylphosphinoxid
TPPO
oxo(triphenyl)phosphorane
Di(phenyl)phosphorylbenzene
Triphenylphosphine monoxide
Trisphenylphosphine oxide | [EINECS(EC#)]
212-338-8 | [Molecular Formula]
C18H15OP | [MDL Number]
MFCD00002080 | [Molecular Weight]
278.28 | [MOL File]
791-28-6.mol |
| Chemical Properties | Back Directory | [Appearance]
White solid | [Melting point ]
150-157 °C(lit.)
| [Boiling point ]
360 °C | [bulk density]
400-450kg/m3 | [density ]
1,212 g/cm3 | [vapor pressure ]
<1 hPa (50 °C) | [Fp ]
180 °C | [storage temp. ]
Store at RT. | [solubility ]
methanol: 25 mg/mL, clear
| [form ]
Crystalline Powder or Flakes | [color ]
White to pink-brown | [Specific Gravity]
1.212 | [Water Solubility ]
slightly soluble | [Hydrolytic Sensitivity]
4: no reaction with water under neutral conditions | [BRN ]
745854 | [Henry's Law Constant]
1.9×104 mol/(m3Pa) at 25℃, Zhang et al. (2010) | [Major Application]
pharmaceutical | [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 | [InChIKey]
FIQMHBFVRAXMOP-UHFFFAOYSA-N | [SMILES]
O=P(c1ccccc1)(c2ccccc2)c3ccccc3 | [LogP]
2.8 | [CAS DataBase Reference]
791-28-6(CAS DataBase Reference) | [NIST Chemistry Reference]
(C6H5)3PO(791-28-6) | [EPA Substance Registry System]
791-28-6(EPA Substance) |
| Questions And Answer | Back Directory | [Preparation]
Many reactions in organic synthesis, such as the Wittig, Staudinger, and phototactic reactions, produce Ph3PO as a byproduct. Ph3PCl2 also produces triphenylphosphine oxide during the conversion of alcohols to chlorinated hydrocarbons: Ph3PCl2 + ROH → Ph3PO + HCl + RCl |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS05 | [Signal word ]
Warning | [Hazard statements ]
H290 | [Precautionary statements ]
P234-P390 | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S36:Wear suitable protective clothing . | [RIDADR ]
3077 | [WGK Germany ]
2
| [RTECS ]
SZ1676000
| [Autoignition Temperature]
590 °C | [TSCA ]
Yes | [REACH Registrations]
Active | [HazardClass ]
9 | [PackingGroup ]
III | [HS Code ]
29310095 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Aquatic Chronic 3 | [Toxicity]
LD50 orally in Rabbit: 685 mg/kg |
| Hazard Information | Back Directory | [Description]
Triphenylphosphine oxide (TPPO) is a coordinating solvent used to activate crystallization of chemical compounds. It has been used in flame retardant applications, as an epoxy cure catalyst, and more recently, to produce nanostructures. | [Chemical Properties]
White solid | [Uses]
Triphenylphosphine Oxide (Orlistat USP Related Compound C) is a catalyst in the conversion of aldehydes into 1,1-dichlorides. Triphenylphosphine Oxide is used as a catalyst for the synthesis of hightly functionalized α-CF3 γ-keto esters. | [Uses]
Triphenylphosphine oxide can be used:
As a catalyst in Appel-type chlorination reaction of acyclic primary and secondary alcohols.
As a catalyst in stereoselective poly and dibromination of α,β-unsaturated esters and β,γ-unsaturated α-ketoester compounds.
As a promotor in the diastereoselective synthesis of α-ribofuranosides through ribofuranosylation of alcohols with ribofuranosyl iodides. | [Uses]
Triphenylphosphine oxide is a phosphine ligand used for coupling reactions, epoxidations, and Michael reactions
| [Definition]
ChEBI: A phosphine oxide in which the substituents on phosphorus are three phenyl groups. | [Synthesis Reference(s)]
Tetrahedron Letters, 31, p. 5463, 1990 DOI: 10.1016/S0040-4039(00)97873-0 | [Flammability and Explosibility]
Notclassified | [reaction suitability]
reagent type: ligand
reaction type: Coupling Reactions
reagent type: ligand
reaction type: Epoxidations
reagent type: ligand
reaction type: Michael Reaction | [Purification Methods]
It crystallises from absolute EtOH and is dried in vacuo. The gold chloride complex has m 177.5-178.5o. [Addison & Sheldon J Chem Soc 2705 1956, Cox & Westheimer J Am Chem Soc 80 5441 1958, Beilstein 16 III 864, 16 1011.] |
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