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[edit]

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[edit]

^ "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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