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378755

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

Quality Level

200

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 2: Flammable solids
Flammable solid
Hazardous rank III

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

378755-100G:4548173961064
378755-VAR:
378755-BULK:
378755-25G:4548173961071

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Synthesis, crystal structure and dynamic behavior of naphthalene-based calix [3] amide: Cyclic trimers of 2-alkylamino-6-naphthoic acid.
Katagiri K, et al.
Journal of Molecular Structure, 891(1), 346-350 (2008)
Synthesis of N-Phosphopeptides Coupled by Dichlorotriphenylphosphorane.
Dong S-Z, et al.
Synthetic Communications, 31(13), 2067-2075 (2001)
Simple and convenient synthesis of tertiary benzanilides using dichlorotriphenylphosphorane.
Azumaya I, et al.
Tetrahedron, 59(13), 2325-2331 (2003)
Murali K Urlam et al.
MedChemComm, 4(6), 932-941 (2013-09-28)
The
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