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From Wikipedia, the free encyclopedia
Triphenylphosphine dichloride
Structural formula
Ball-and-stick model
Ball-and-stick model
Space-filling model
Space-filling model
Names
IUPAC name
?
Other names
Dichlorotriphenylphosphorane
Identifiers
ChemSpider
Properties
C18H15Cl2P
Molar mass 333.19 g/mol
Melting point 176 °C[1], 85-100 °C[2]
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Tracking categories (test):

Triphenylphosphine dichloride, Ph3PCl2, 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]

Synthesis

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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]

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

Structure

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In polar solvents such as acetonitrile or dichloromethane solutions, Ph3PCl2 adopts an ionic structure[3], [Ph3PCl]Cl, whereas in non-polar solvents like diethyl ether it exists as a non-solvated trigonal bipyramidal molecule.[4].

References

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  1. ^ a b V. Grignard, J. Savard (1931). Compt. rend. 192: 592–5. {{cite journal}}: Missing or empty |title= (help)
  2. ^ a b c e-EROS Encyclopedia of Reagents for Organic Synthesis, doi:10.1002/047084289X.rt371
  3. ^ S. M. Godfrey, C. A. McAuliffe, R. G. Pritchard, J. M. Sheffield (1996). Chem. Commun.: 2521−2522. doi:10.1039/CC9960002521. {{cite journal}}: Missing or empty |title= (help)CS1 maint: multiple names: authors list (link)
  4. ^ S. M. Godfrey, C. A. McAuliffe, J. M. Sheffield (1998). Chem. Commun.: 921−922. doi:10.1039/a800820e. {{cite journal}}: Missing or empty |title= (help)CS1 maint: multiple names: authors list (link)