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
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Toxic, reacts with water to release HCl |
GHS labelling:[1] | |
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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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
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