Chlorodiisopropylphosphine
Chemical compound
From Wikipedia, the free encyclopedia
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.
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| Names | |
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| Preferred IUPAC name
Di(propan-2-yl)phosphinous chloride | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.157.609 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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] | |
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| 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).
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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]