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<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> | + | {{FixBunching|mid}} |
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| + | | Name = PBr{{su|b=4|p=+}}Br<sup>−</sup> | ||
| + | | IUPACName = Tetrabromophosphonium bromide | ||
| + | | Section1 = {{Chembox Identifiers | ||
| + | | StdInChI=1S/Br4P.BrH/c1-5(2,3)4;/h;1H/q+1;/p-1 | ||
| + | | StdInChIKey = BVHDGQDJOKBOHK-UHFFFAOYSA-M | ||
| + | | CASNo = 7789-69-7 | ||
| + | | EINECS = 232-186-6 | ||
| + | }} | ||
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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><ref>{{citation | first1 = Arthur | last1 = Finch | first2 = Peter N. | last2 = Gates | first3 = Alan S. | last3 = Muir | title = Variable-temperature Raman spectra of phosphorus(V) chloride and bromide deposited at 15 K | journal = J. Chem. Soc., Chem. Commun. | year = 1981 | pages = 812–14 | doi = 10.1039/C39810000812}}.</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 10:23, 7 January 2011
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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][4] It is used as a brominating agent, converting carboxylic acids to acyl bromides[1] and phenols and secondary alcohols to the corresponding bromides.[5][6]
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.
- ↑ Finch, Arthur; Gates, Peter N.; Muir, Alan S. Variable-temperature Raman spectra of phosphorus(V) chloride and bromide deposited at 15 K. J. Chem. Soc., Chem. Commun. 1981, 812–14. DOI: 10.1039/C39810000812.
- ↑ 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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