Triphenylphosphine dichloride

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Names
Preferred IUPAC name

Dichlorotri(phenyl)-λ5-phosphane

Other names

Dichlorotriphenylphosphorane

Identifiers

CAS Number

* 2526-64-9 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 228579 N

PubChem CID

* 260420

UNII |

* 6CL2293LZ3 Y

InChI

* 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 N

Key: ASWXNYNXAOQCCD-UHFFFAOYSA-N N

SMILES

* ClP(Cl)(c1ccccc1)(c1ccccc1)c1ccccc1

Properties

Chemical formula

| C18H15Cl2P
Molar mass | 333.19 g/mol
Melting point |  176 °C (349 °F; 449 K)[1] 85-100 °C[2]

Solubility in water

| Reacts
Related compounds

Related compounds

| Phosphoranes
Triphenylphosphine
Phosphorus trichloride
Phosphorus pentachloride
Phosphorus halides
Tetraphenylphosphonium chloride

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Infobox references

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Triphenylphosphine dichloride, (C6H5)3PCl2, is a chlorinating agent widely used in organic chemistry. Applications include the conversion of alcohols and ethers to alkyl chlorides, the cleavage of epoxides to vicinal dichlorides and the chlorination of carboxylic acids to acyl chlorides.[2]

## Structure

In polar solvents such as acetonitrile, Ph3PCl2 adopts an ionic phosphonium salt structure, [Ph3PCl+]Cl−,[3] whereas in non-polar solvents like diethyl ether it exists as a non-solvated trigonal bipyramidal molecule.[4] Two [Ph3PCl+] species can also adopt an unusual dinuclear ionic structure--both interacting with a Cl− via long Cl–Cl contacts.[3]

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## Synthesis

Triphenylphosphine dichloride is usually prepared fresh by the addition of chlorine to triphenylphosphine.

Ph3P + Cl2 → Ph3PCl2

Both reagents are typically used in solution to ensure the correct stoichiometry.[2]

Ph3PCl2 can also be obtained by the reaction of iodobenzene dichloride (PhICl2) and triphenylphosphine.[5]

Alternatively, Ph3PCl2 can be obtained by chlorination of triphenylphosphine oxide with, for example, phosphorus trichloride, as in Grignard's original 1931 synthesis.[1]

## References

1. ↑ 1.0 1.1 Victor Grignard, J. Savard (1931). Comptes rendus de l'Académie des sciences 192: 592–5.
2. ↑ 2.0 2.1 2.2 e-EROS Encyclopedia of Reagents for Organic Synthesis, doi:10.1002/047084289X.rt371
3. ↑ 3.0 3.1 S. M. Godfrey; C. A. McAuliffe; R. G. Pritchard; J. M. Sheffield (1996). "An X-ray crystallorgraphic study of the reagent Ph3PCl2; not charge-transfer, R3P–Cl–Cl, trigonal bipyramidal or [R3PCl]Cl but an unusual dinuclear ionic species, [Ph3PCl+⋯Cl–⋯+CIPPH3]Cl containing long Cl–Cl contacts". Chemical Communications (22): 2521–2522. doi:10.1039/CC9960002521.
4. ↑ S. M. Godfrey; C. A. McAuliffe; J. M. Sheffield (1998). "Structural dependence of the reagent Ph3PCl2 on the nature of the solvent, both in the solid state and in solution; X-ray crystal structure of trigonal bipyramidal Ph3PCl2, the first structurally characterised five-coordinate R3PCl2 compound". Chem. Commun. (8): 921–922. doi:10.1039/a800820e.
5. ↑ Carle, M. S., Shimokura, G. K. and Murphy, G. K. (2016), Iodobenzene Dichloride in the Esterification and Amidation of Carboxylic Acids: In-Situ Synthesis of Ph3PCl2. Eur. J. Org. Chem., 2016: 3930–3933. {{DOI:10.1002/ejoc.201600714}}

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*[CID]: Compound ID