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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

Signal Word

Danger

Hazard Statements

H228,H314,H350

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

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)
The preparation of dimethyl phosphorochloridite and its homologs from trialkyl phosphites and dichlorotriphenylphosphorane.
Majewski P.
Phosph. Sulfur Relat. Elem., 33(1-2), 37-39 (1987)
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