Difference between revisions of "Phosphorus pentabromide"
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| − | '''Phosphorus pentabromide''', PBr<sub>5</sub>, is the highest [[bromide]] of [[phosphorus]]. The PBr<sub>5</sub> molecule is unknown: the compound exists as PBr{{su|b=4|p=+}}Br<sup>−</sup> in the solid state, and dissociates to [[phosphorus tribromide]] and [[bromine]] in the gas phase.<ref>{{Greenwood&Earnshaw1st|pages=571–75}}.</ref> It is used as a brominating agent, converting [[carboxylic acid]]s to [[acyl bromide]]s and [[phenol]]s and secondary [[alcohol]]s to the corresponding bromides.<ref | + | '''Phosphorus pentabromide''', PBr<sub>5</sub>, is the highest [[bromide]] of [[phosphorus]]. The PBr<sub>5</sub> molecule is unknown: the compound exists as PBr{{su|b=4|p=+}}Br<sup>−</sup> in the solid state, and dissociates to [[phosphorus tribromide]] and [[bromine]] in the gas phase.<ref>{{Greenwood&Earnshaw1st|pages=571–75}}.</ref> It is used as a brominating agent, converting [[carboxylic acid]]s to [[acyl bromide]]s<ref name="Kirk-Othmer"/> and [[phenol]]s and secondary [[alcohol]]s to the corresponding bromides.<ref>{{citation | title = Substituted Bromoquinolines | first1 = C. E. | last1 = Kaslow | first2 = Max M. | last2 = Marsh | journal = J. Org. Chem. | year = 1947 | volume = 12 | issue = 3 | pages = 456–59 | doi = 10.1021/jo01167a014}}.</ref><ref>{{citation | title = Conformational Analysis. V. The Reaction of ''cis''- and ''trans''-4-t-Butylcyclohexanol and ''trans''-4-Methylcyclohexanol with Phosphorus Pentabromide. Syntheses of Alkylcyclohexyl Bromides | first1 = Ernest L. | last1 = Eliel | first2 = Ralph G. | last2 = Haber | journal = J. Org. Chem. | year = 1959 | volume = 24 | issue = 2 | pages = 143–51 | doi = 10.1021/jo01084a001}}.</ref> |
==Notes and references== | ==Notes and references== | ||
Revision as of 10:11, 7 January 2011
| Phosphorus pentabromide | |
|---|---|
| Other names | Phosphorus(V) bromide |
| Identifiers | |
| InChI | InChI=1/Br5P/c1-6(2,3,4)5 |
| InChIKey | QRKVRHZNLKTPGF-UHFFFAOYAR |
| Standard InChI | InChI=1S/Br5P/c1-6(2,3,4)5 |
| Standard InChIKey | QRKVRHZNLKTPGF-UHFFFAOYSA-N |
| CAS number | [] |
| EC number | |
| ChemSpider | |
| Properties[1] | |
| Chemical formula | PBr5 |
| Molar mass | 430.49 g mol−1 |
| Appearance | red-yellow solid |
| Melting point |
83.8 °C |
| Boiling point |
106 °C decomp. |
| Solubility in water | hydrolyzes |
| Hazards[2] | |
| EU index number | not listed |
| GHS pictograms | 
|
| GHS signal word | DANGER |
| GHS hazard statements | H314, H318 |
| GHS precautionary statements | P260, P264, P280, P301+330+331, P303+361+353, P363, P304+340, P310, P321, P305+351+338, P405, P501 |
| Related compounds | |
| Other anions | Phosphorus pentafluoride Phosphorus pentachloride Phosphorus pentaiodide |
| Other cations | Arsenic pentabromide Antimony pentabromide Bismuth pentabromide |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
Phosphorus pentabromide, PBr5, is the highest bromide of phosphorus. The PBr5 molecule is unknown: the compound exists as PBr+4Br− in the solid state, and dissociates to phosphorus tribromide and bromine in the gas phase.[3] It is used as a brominating agent, converting carboxylic acids to acyl bromides[1] and phenols and secondary alcohols to the corresponding bromides.[4][5]
Notes and references
Notes
References
- ↑ 1.0 1.1 Ukeles, S. D.; Freiberg, M. Bromine, Inorganic Compounds. In Kirk-Othmer Encyclopedia of Chemical Technology; John Wiley: New York, 2002. DOI: 10.1002/0471238961.021815131001031.
- ↑ HSNO Chemical Classification Information Database, <http://www.ermanz.govt.nz/Chemicals/ChemicalDisplay.aspx?SubstanceID=14517> (accessed 7 January 2011), New Zealand Environmental Risk Management Authority.
- ↑ Greenwood, Norman N.; Earnshaw, A. Chemistry of the Elements; Pergamon: Oxford, 1984; pp 571–75. ISBN 0-08-022057-6.
- ↑ Kaslow, C. E.; Marsh, Max M. Substituted Bromoquinolines. J. Org. Chem. 1947, 12 (3), 456–59. DOI: 10.1021/jo01167a014.
- ↑ Eliel, Ernest L.; Haber, Ralph G. Conformational Analysis. V. The Reaction of cis- and trans-4-t-Butylcyclohexanol and trans-4-Methylcyclohexanol with Phosphorus Pentabromide. Syntheses of Alkylcyclohexyl Bromides. J. Org. Chem. 1959, 24 (2), 143–51. DOI: 10.1021/jo01084a001.
External links
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See also the corresponding article on Wikipedia. |
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