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T84654

Sigma-Aldrich

Triphenyl phosphite

97%

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

vapor density

10.7 (vs air)

Quality Level

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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1 of 4

This Item
287822240907247049
vibrant-m

T84654

Triphenyl phosphite

vibrant-m

287822

Tri(o-tolyl)phosphine

vibrant-m

240907

Trimethyl phosphite

vibrant-m

247049

Tributylphosphine

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

reaction suitability

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

reaction suitability

reaction type: Cross Couplings, reaction type: Silylations, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: Heck Reaction, reagent type: ligand
reaction type: Negishi Coupling, reagent type: ligand
reaction type: Stille Coupling, reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

reaction suitability

-

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: Acetylations, reagent type: ligand
reaction type: Addition Reactions, reagent type: ligand
reaction type: Stille Coupling

mp

22-24 °C (lit.)

mp

123-125 °C (lit.)

mp

−78 °C (lit.)

mp

-

density

1.184 g/mL at 25 °C (lit.)

density

-

density

1.052 g/mL at 25 °C (lit.)

density

0.81 g/mL at 25 °C (lit.)

bp

360 °C (lit.)

bp

-

bp

111-112 °C (lit.)

bp

150 °C/50 mmHg (lit.)

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


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Customers Also Viewed

Slide 1 of 5

1 of 5

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)
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)
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)
Ciby J Abraham et al.
Journal of the American Chemical Society, 130(50), 17085-17094 (2008-12-05)
We report a detailed synthetic and mechanistic study of an unusual bifunctional, sequential hetero-Diels-Alder/ring-opening reaction in which chiral, metal complexed ketene enolates react with o-quinones to afford highly enantioenriched, alpha-hydroxylated carbonyl derivatives in excellent yield. A number of Lewis acids

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