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Merck
CN

T84654

Triphenyl phosphite

97%

Synonym(s):

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

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About This Item

Linear Formula:
(C6H5O)3P
CAS Number:
Molecular Weight:
310.28
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1079456
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Product Name

Triphenyl phosphite, 97%

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

SMILES string

O(P(Oc1ccccc1)Oc2ccccc2)c3ccccc3

InChI key

HVLLSGMXQDNUAL-UHFFFAOYSA-N

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.)

Quality Level

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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.

General description

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

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

WGK 2

flash_point_f

410.0 °F

flash_point_c

210 °C

Regulatory Information

危险化学品
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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)
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)
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)
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)

Related Content

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

Catalexis平台通过数字化优化催化剂筛选,识别出交叉偶联反应最有效的膦配体,从而增强催化作用。

Phosphine Ligand Application Guide

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