Chlorodiisopropylphosphine

Chlorodiisopropylphosphine
Names
	Preferred IUPAC name Di(propan-2-yl)phosphinous chloride
Identifiers
CAS Number	40244-90-4;
3D model (JSmol)	Interactive image;
ChemSpider	469344;
ECHA InfoCard	100.157.609
EC Number	629-426-0;
PubChem CID	538967;
UNII	5FG5N54CYB ;
CompTox Dashboard (EPA)	DTXSID10337132 ;
	InChI 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;
	SMILES CC(C)P(C(C)C)Cl;
Properties
Chemical formula	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)
Solubility in water	Reacts
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Toxic, reacts with water to release HCl
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H314
Precautionary statements	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

^ "Chlorodiisopropylphosphine". pubchem.ncbi.nlm.nih.gov.
^ W. Voskuil; J. F. Arens (1968). "Chlorodiisopropylphosphine". Org. Synth. 48: 47. doi:10.15227/orgsyn.048.0047.
^ for example: Pandarus, V., Zargarian, D., "New Pincer-Type Diphosphinito (POCOP) Complexes of Nickel", Organometallics 2007, volume 26, 4321. doi:10.1021/om700400x

[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] r 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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