Chlorodiisopropylphosphine

Chlorodiisopropylphosphine is an organophosphorus compound with the formula [(CH3)2CH]2PCl. It is a colorless liquid that reacts with water and oxygen. The compound is used to prepare tertiary phosphines and phosphinite ligands.

Chlorodiisopropylphosphine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.157.609
Properties
C6H14ClP
Molar mass 152.60 g·mol−1
Appearance colorless liquid
Density 0.959 g/mL at 25 °C
Boiling point 46-47 °C (10 mm of Hg)
Hazards
Main hazards toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis and reactions

The compound is prepared by treating phosphorus trichloride with the Grignard reagent isopropylmagnesium chloride:[1]

PCl3 + 2 (CH3)2CHMgCl → [(CH3)2CH]2PCl + 2 MgCl2

Relative to the reaction of less hindered Grignard reagents with PCl3, this reaction affords a superior yield of the monochloro derivative.

Chlorodiisopropylphosphine reacts with Grignard reagents and organolithium compounds to give phosphines:

[(CH3)2CH]2PCl + RM → [(CH3)2CH]2PR + MCl

Chlorodiisopropylphosphine reacts with alcohols and phenols to give phosphinites, this reaction typically is conducted in the presence of a base:

[(CH3)2CH]2PCl + ROH → [(CH3)2CH]2POR + HCl

Phosphinites are versatile ligands.[2]

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References
  1. W. Voskuil and J. F. Arens (1968). "Chlorodiisopropylphosphine". Org. Synth. 48: 47. doi:10.15227/orgsyn.048.0047.CS1 maint: uses authors parameter (link)
  2. for example: Pandarus, V., Zargarian, D., "New Pincer-Type Diphosphinito (POCOP) Complexes of Nickel", Organometallics 2007, volume 26, 4321. doi:10.1021/om700400x
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