Chlorodiisopropylphosphine
Names
Preferred IUPAC name
Di(propan-2-yl)phosphinous chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.157.609
EC Number
  • 629-426-0
UNII
  • 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)
Reacts
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic, reacts with water to release HCl
GHS labelling:[1]
GHS02: FlammableGHS05: Corrosive
Danger
H225, H314
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.

Synthesis and reactions

The compound is prepared by treating phosphorus trichloride with the Grignard reagent isopropylmagnesium chloride:[2]

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.[3]

References

  1. ↑ "Chlorodiisopropylphosphine". pubchem.ncbi.nlm.nih.gov.
  2. ↑ W. Voskuil; J. F. Arens (1968). "Chlorodiisopropylphosphine". Org. Synth. 48: 47. doi:10.15227/orgsyn.048.0047.
  3. ↑ 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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