User:Benjah-bmm27/PPh3Cl2/draft

Triphenylphosphine dichloride

Ball-and-stick model Space-filling model
Names
IUPAC name ?
Other names Dichlorotriphenylphosphorane
Identifiers
CAS Number	2526-64-9
ChemSpider	NA
Properties
Chemical formula	C18H15Cl2P
Molar mass	333.19 g/mol
Melting point	176 °C, 85-100 °C
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tracking categories (test):

• SizeSet
• PairSizeSet

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.

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.

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

Structure

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

• 
• 
•