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 | + | {{FixBunching|beg}} |
| + | {{chembox | ||
| + | | Name = Phosphorus pentabromide | ||
| + | | OtherNames = Phosphorus(V) bromide | ||
| + | | Section1 = {{Chembox Identifiers | ||
| + | | ChemSpiderID = 56429 | ||
| + | | InChI=1/Br5P/c1-6(2,3,4)5 | ||
| + | | InChIKey = QRKVRHZNLKTPGF-UHFFFAOYAR | ||
| + | | StdInChI=1S/Br5P/c1-6(2,3,4)5 | ||
| + | | StdInChIKey = QRKVRHZNLKTPGF-UHFFFAOYSA-N | ||
| + | | CASNo = 7789-69-7 | ||
| + | | EINECS = 232-186-6 | ||
| + | }} | ||
| + | | Section2 = {{Chembox Properties | ||
| + | | Reference = <ref name="Kirk-Othmer">{{Kirk-Othmer | first1 = S. D. | last1 = Ukeles | first2 = M. | last2 = Freiberg | contribution = Bromine, Inorganic Compounds | doi = 10.1002/0471238961.021815131001031 | year = 2002}}.</ref><ref name="Struct">{{citation | first1 = W. | last1 = Gabes | first2 = K. | last2 = Olie | title = Refinement of the crystal structure of phosphorus pentabromide, PBr<sub>5</sub> | journal = Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. | year = 1970 | volume = 26 | pages = 443–44 | doi = 10.1107/S0567740870002595}}.</ref> | ||
| + | | Formula = PBr<sub>5</sub> | ||
| + | | MolarMass = 430.49 g mol<sup>−1</sup> | ||
| + | | Appearance = red-yellow solid | ||
| + | | Density = 3.595 g cm<sup>−3</sup> | ||
| + | | Solubility = hydrolyzes | ||
| + | | MeltingPt = 83.8 °C | ||
| + | | BoilingPt = 106 °C ''decomp.'' | ||
| + | }} | ||
| + | | Section7 = {{Chembox Hazards | ||
| + | | Reference = <ref>{{GHS class NZ|id=14517|accessdate=2011-1-7}}.</ref> | ||
| + | | EUIndex = not listed | ||
| + | | MSDS = | ||
| + | | GHSPictograms = {{GHS05|Skin Corr. 1C, Eye Dam. 1}} | ||
| + | | GHSSignalWord = DANGER | ||
| + | | HPhrases = {{H-phrases|314|318}} | ||
| + | | PPhrases = {{P-phrases|260|264|280| 301+330+331|303+361+353|363|304+340|310|321|305+351+338| 405|501}} | ||
| + | }} | ||
| + | | Section8 = {{Chembox Related | ||
| + | | OtherAnions = [[Phosphorus pentafluoride]]<br />[[Phosphorus pentachloride]]<br/>[[Phosphorus pentaiodide]] | ||
| + | | OtherCations = [[Arsenic pentabromide]]<br/>[[Antimony pentabromide]]<br/>[[Bismuth pentabromide]] | ||
| + | | OtherCpds = [[Phosphorus tribromide]] | ||
| + | }} | ||
| + | }} | ||
| + | {{FixBunching|mid}} | ||
| + | {{chembox | ||
| + | | Name = 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 | ||
| + | }} | ||
| + | | Section2 = {{Chembox Properties | ||
| + | | Formula = PBr{{su|b=4|p=+}}Br<sup>−</sup> | ||
| + | | MolarMass = 430.49 g mol<sup>−1</sup> | ||
| + | }} | ||
| + | | Section3 = {{Chembox Structure | ||
| + | | Reference = <ref name="Struct"/> | ||
| + | | SpaceGroup = P''bcm'' (No. 57) | ||
| + | | LattConst_a = 566.3(3) pm | ||
| + | | LattConst_b = 1703.1(5) pm | ||
| + | | LattConst_c = 824.7(5) pm | ||
| + | | Coordination = tetrahedral (P) | ||
| + | | MolShape = ''T<sub>d</sub>'': ''r''(P–Br) = 215 pm | ||
| + | }} | ||
| + | }} | ||
| + | {{FixBunching|end}} | ||
| + | '''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== | ||
Latest revision as of 14:50, 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.[4][5] It is used as a brominating agent, converting carboxylic acids to acyl bromides[1] and phenols and secondary alcohols to the corresponding bromides.[6][7]
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.
- ↑ 2.0 2.1 Gabes, W.; Olie, K. Refinement of the crystal structure of phosphorus pentabromide, PBr5. Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1970, 26, 443–44. DOI: 10.1107/S0567740870002595.
- ↑ 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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