Skip to Content
Merck
All Photos(3)

Key Documents

378755

Sigma-Aldrich

Dichlorotriphenylphosphorane

95%

Synonym(s):

Triphenylphosphine dichloride

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
(C6H5)3PCl2
CAS Number:
Molecular Weight:
333.19
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

95%

form

solid

mp

85 °C (dec.) (lit.)

functional group

phosphine

SMILES string

ClP(Cl)(c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C18H15Cl2P/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

ASWXNYNXAOQCCD-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

General description

Dichlorotriphenylphosphorane (Triphenylphosphine dichloride, PPh3Cl2) is a phosphorous halide. Stability and reactivity of dichlorotriphenylphosphorane have been studied by solid state 31P NMR spectroscopy. It participates in the conversion of carboxylic esters to acid halides and mechanism of this cleavage has been investigated. Modified method has been proposed in which dichlorotriphenylphosphorane participates in the synthesis of tertiary amides.

Application

Dichlorotriphenylphosphorane may be used in the synthesis of the following:
  • tertiary benzanilide derivatives
  • N-phosphodipeptides
  • dialkyl phosphorochloridites based on the reaction of trialkyl phosphites
  • naphthalene ring-based calix[3]amide, via reaction with 6-amino-2-naphthoic acid
  • C2v-symmetrical cyclic tetramers of aromatic amides

Signal Word

Danger

Hazard Statements

Hazard Classifications

Carc. 1B - Eye Dam. 1 - Flam. Sol. 2 - Skin Corr. 1B

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

68.0 °F - closed cup

Flash Point(C)

20 °C - closed cup


Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

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

Visit the Document Library

Cleavage of carboxylic acid esters to acid chlorides with dichlorotriphenylphosphorane.
Burton DKJ and Koppes WM.
The Journal of Organic Chemistry, 40(21), 3026-3032 (1975)
Nina C Gonnella et al.
Magnetic resonance in chemistry : MRC, 47(6), 461-464 (2009-03-07)
Solid state (31)P NMR spectroscopy was used to examine, monitor and quantify the compound integrity of the chemical reagent dichlorotriphenylphosphorane. Comparison was also made with solution (31)P NMR spectra which showed that this highly reactive species could be observed in
Construction of anomalously bent biphenyl structure using conformational properties of calix [4] amide.
Tominaga M, et al.
Tetrahedron Letters, 47(52), 346-350 (2006)
Murali K Urlam et al.
MedChemComm, 4(6), 932-941 (2013-09-28)
The
Synthesis of N-Phosphopeptides Coupled by Dichlorotriphenylphosphorane.
Dong S-Z, et al.
Synthetic Communications, 31(13), 2067-2075 (2001)

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