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Sigma-Aldrich

Triphenylphosphine diiodide

technical grade, 90%

Synonym(s):

Diiodotriphenylphosphorane

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About This Item

Linear Formula:
(C6H5)3PI2
CAS Number:
6396-07-2
Molecular Weight:
516.09
Beilstein/REAXYS Number:
2740417
MDL number:
MFCD00216568
UNSPSC Code:
12352101
PubChem Substance ID:
24866095
NACRES:
NA.06

grade

technical grade

assay

90%

form

solid

mp

210-220 °C (lit.)

SMILES string

IP(I)(c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C18H15I2P/c19-21(20,16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H

InChI key

NSWZEXJQHIXCFL-UHFFFAOYSA-N

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Application

Triphenylphosphine diiodide (Ph3P. I2) can be used as a reagent:
  • To facilitate the conversion of alcohol, thiol, and enol functional groups into alkyl iodides via formation of alkoxyphosphonium iodide.
  • To prepare β-iodo-α,β-unsaturated ketones from cyclic β-diketones in the presence of triethyl amine.
  • In the synthesis of alkyl nitrates from alcohols.
  • In the Beckmann rearrangement reaction to synthesize lactams from cycloalkanone oxime.
  • For the preparation of aromatic and aliphatic carboxylic acid esters in the presence of N,N-dimethylaminopyridine.

Ph3P. I2 can also be used to reduce graphene oxide for the production of graphene nanosheets under mild and environmentally friendly conditions.

pictograms

Health hazardCorrosion
GHS08,GHS05

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Repr. 2 - Resp. Sens. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Triphenylphosphine-Iodine
Dormoy J-R
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
New approach for the reduction of graphene oxide with triphenylphosphine dihalide
Shin H-S et al.
Royal Society of Chemistry Advances, 6(23), 18809-18813 (2016)
One-Pot Synthesis of Carboxylic Acid Esters in Neutral and Mild Conditions by Triphenylphosphine Dihalide [Ph 3 PX 2 (X= Br, I)].
Sardarian Alireza R, et al.
Acta Chimica Slovenica, 56(3) (2009)

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