Chlorodiphenylphosphine
From Wikipedia, the free encyclopedia
| Chlorodiphenylphosphine | |
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| IUPAC name | chlorodiphenylphosphine |
| Other names | p-chlorodiphenylphosphine, diphenyl phosphine chloride, diphenylchlorophosphine, diphenylphosphinous chloride |
| Identifiers | |
| CAS number | [1079-66-9] |
| Properties | |
| Molecular formula | C12H10ClP |
| Molar mass | 220.63776 g mol-1 |
| Appearance | clear to light yellow liquid |
| Density | 1.229 g cm-3 |
| Boiling point |
320 ˚C |
| Solubility in water | Reacts with water |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Chlorodiphenylphosphine (Ph2PCl) is known by many different names. It is a liquid with a very pungent odor often described as being garlic-like, detectable even in the ppb range. Like other halophosphines, Ph2PCl is highly reactive with many nucleophiles, water, and even air.[1] Halophosphines are easily oxidized and used as reagents in the synthesis of many different phosphines.[2]
[edit] Synthesis
Ph2PCl is made on a commercial scale from benzene and phosphorus trichloride (PCl3). Benzene is reacted with phosphorus trichloride at extreme temperatures, around 600 ˚C, yielding phenylphosphinous dichloride (PhPCl2). Disproportionation of PhPCl2 in the gas phase at high temperatures results in chlorodiphenylphosphine.[2][1]
- 2 PhPCl2 → Ph2PCl + PCl3
[edit] Uses
Ph2PCl, along with other members of the halophosphine family, is widely used in the synthesis of various phosphines. For example: where R= alkyl or aryl group
Ph2PCl + MgRX → Ph2PR + MgClX
The phosphines produced from reactions with Ph2PCl are further developed and used as pesticides (EPN or ethyl p-nitrophenyl thionobenzenephosphonate), stabilizers for plastics (Sandostab P-EPQ), various halogen compound catalysts, flame retardants (cyclic phosphinocarboxylic anhydride), as well as UV-hardening paint systems (used in dental materials) making Ph2PCl an important intermediate in the industrial world.[2][1]
[edit] References
- ^ a b c Svara, J.; Weferling, N.; Hofmann, T. Phosphorus Compounds, Organic, In Ullmann's Encyclopedia of Industrial Chemistry, 7th ed.; John Wiley & Sons, Inc.: 2008; DOI: 10.1002/14356007.a19_545.pub2; Accessed: February 18, 2008.
- ^ a b c Quin, L. D. A Guide to Organophosphorus Chemistry; Wiley IEEE: New York, 2000; pp 44-69. ISBN 0471318248
