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
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 Y
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:[1]
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

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]