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
Names
Preferred IUPAC name
Di(propan-2-yl)phosphinous chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.157.609
  • InChI=1S/C6H14ClP/c1-5(2)8(7)6(3)4/h5-6H,1-4H3
    Key: JZPDBTOWHLZQFC-UHFFFAOYSA-N
  • InChI=1/C6H14ClP/c1-5(2)8(7)6(3)4/h5-6H,1-4H3
    Key: JZPDBTOWHLZQFC-UHFFFAOYAH
  • CC(C)P(C(C)C)Cl
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
Occupational safety and health (OHS/OSH):
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]

References
  1. W. Voskuil and J. F. Arens (1968). "Chlorodiisopropylphosphine". Org. Synth. 48: 47. doi:10.15227/orgsyn.048.0047.{{cite journal}}: 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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