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T84654

Sigma-Aldrich

Triphenyl phosphite

97%

Synonym(s):

(PhO)3P, P(OPh)3, Triphenoxyphosphine

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About This Item

Linear Formula:
(C6H5O)3P
CAS Number:
101-02-0
Molecular Weight:
310.28
Beilstein/REAXYS Number:
1079456
MDL number:
MFCD00003032
UNSPSC Code:
12352108
PubChem Substance ID:
24900533

vapor density

10.7 (vs air)

Quality Level

200

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.)

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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General description

Triphenyl phosphite (TPP) is an organophosphorus compound that serves as a versatile reagent in the synthesis of phosphorus ligands.

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.

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT RE 2

target_organs

Nervous system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 2

flash_point_f

410.0 °F

flash_point_c

210 °C

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
Singlet oxygen sources in ozone chemistry
Murray RW and Kaplan M
Journal of the American Chemical Society, 90(2), 537-538 (1968)
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)
Peptide synthesis using triphenyl phosphite and imidazole
Mitin YV and Glinskaya OV
Tetrahedron Letters, 10(60), 5267-5270 (1969)
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