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Sigma-Aldrich

Dichlorotriphenylphosphorane

95%

Synonym(s):

Triphenylphosphine dichloride

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About This Item

Linear Formula:
(C6H5)3PCl2
CAS Number:
2526-64-9
Molecular Weight:
333.19
MDL number:
MFCD00010359
UNSPSC Code:
12352100
PubChem Substance ID:
24863576
NACRES:
NA.22

assay

95%

form

solid

mp

85 °C (dec.) (lit.)

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

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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

signalword

Danger

Hazard Classifications

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

Storage Class

4.1B - Flammable solid hazardous materials

wgk_germany

WGK 3

flash_point_f

68.0 °F - closed cup

flash_point_c

20 °C - closed cup

Certificates of Analysis (COA)

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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
Murali K Urlam et al.
MedChemComm, 4(6), 932-941 (2013-09-28)
The
Construction of anomalously bent biphenyl structure using conformational properties of calix [4] amide.
Tominaga M, et al.
Tetrahedron Letters, 47(52), 346-350 (2006)
Synthesis of N-Phosphopeptides Coupled by Dichlorotriphenylphosphorane.
Dong S-Z, et al.
Synthetic Communications, 31(13), 2067-2075 (2001)
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