Skip to Content
Merck
CN
All Photos(1)

Documents

Safety Information

T84654

Sigma-Aldrich

Triphenyl phosphite

97%

Sign Into View Organizational & Contract Pricing
All Photos(1)
Synonym(s):
(PhO)3P, P(OPh)3, Triphenoxyphosphine
Linear Formula:
(C6H5O)3P
CAS Number:
101-02-0
Molecular Weight:
310.28
Beilstein:
1079456
MDL number:
MFCD00003032
UNSPSC Code:
12352108
PubChem Substance ID:
24900533
NACRES:
NA.22

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

Looking for similar products? Visit Product Comparison Guide

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.

Signal Word

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

WGK

WGK 2

Flash Point(F)

410.0 °F

Flash Point(C)

210 °C

Regulatory Information

危险化学品

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

One-pot syntheses of sterically shielded phosphorus ligands by selective stepwise nucleophilic substitution at triphenyl phosphite
J Keller, et al.
Synthesis, 2006, 354-365 (2006)
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)
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)
Singlet oxygen sources in ozone chemistry
Murray RW and Kaplan M
Journal of the American Chemical Society, 90(2), 537-538 (1968)
View All Related Papers

Related Content

Catalexis Catalyst Screening Platform

The Catalexis platform enhances catalysis by digitally optimizing catalyst selection to identify the most effective phosphine ligands for cross-coupling reactions.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service