T84654

Sigma-Aldrich

Triphenyl phosphite

97%

Synonym(s):
(PhO)3P, Triphenoxyphosphine, P(OPh)3
Linear Formula:
(C6H5O)3P
CAS Number:
Molecular Weight:
310.28
Beilstein/REAXYS Number:
1079456
MDL number:
PubChem Substance ID:

Quality Level

vapor density

10.7 (vs air)

vapor pressure

5 mmHg ( 205 °C)

assay

97%

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Alkylations

reagent type: ligand
reaction type: Cycloadditions

reagent type: ligand
reaction type: Heck Reaction

reagent type: ligand
reaction type: Olefinations

reagent type: ligand
reaction type: Stille Coupling

reagent type: ligand
reaction type: Wittig Reaction

refractive index

n20/D 1.59 (lit.)

bp

360 °C (lit.)

mp

22-24 °C (lit.)

density

1.184 g/mL at 25 °C (lit.)

functional group

phosphine

SMILES string

O(P(Oc1ccccc1)Oc2ccccc2)c3ccccc3

InChI

1S/C18H15O3P/c1-4-10-16(11-5-1)19-22(20-17-12-6-2-7-13-17)21-18-14-8-3-9-15-18/h1-15H

InChI key

HVLLSGMXQDNUAL-UHFFFAOYSA-N

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Application

Triphenyl phosphite can be used:
  • As a source of phosphorus and as a ligand for the synthesis of transition metal phosphide nanoparticles via heating-up process.
  • To convert alcohols to alkyl halides.
  • As a peptide coupling agent.
  • As a low-temperature source of singlet oxygen after forming an adduct with ozone.
  • To synthesize bromotriphenoxyphosphonium bromide, a brominating agent, by reacting with bromine.

Packaging

3 kg in glass bottle
5, 500 g in glass bottle

pictograms

Exclamation markEnvironment

signalword

Warning

RIDADR

UN 3077 9 / PGIII

WGK Germany

WGK 2

Flash Point F

410.0 °F

Flash Point C

210 °C

Certificate of Analysis

Certificate of Origin

Triphenyl Phosphite as the Phosphorus Source for the Scalable and Cost-Effective Production of Transition Metal Phosphides
Liu J, et al.
Chemistry of Materials, 30(5), 1799-1807 (2018)
Singlet oxygen sources in ozone chemistry
Murray RW and Kaplan M
Journal of the American Chemical Society, 90(2), 537-538 (1968)
Development of a Safe and Robust Process for the Large-Scale Preparation of a Vinyl Bromide from a Ketone Using a (PhO)3P/Br2-Derived Reagent
Likhite N, et al.
Organic Process Research & Development, 20(5), 977-981 (2016)
Peptide synthesis using triphenyl phosphite and imidazole
Mitin YV and Glinskaya OV
Tetrahedron Letters, 10(60), 5267-5270 (1969)
458. The organic chemistry of phosphorus. Part I. Some new methods for the preparation of alkyl halides
Landauer SR and Rydon HN
Journal of the Chemical Society, 30(5), 2224-2234 (1953)

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