Difference between revisions of "Phosphorus pentabromide"

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| Name = Phosphorus pentabromide
 
| Name = Phosphorus pentabromide
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   }}
 
   }}
 
| Section2 = {{Chembox Properties
 
| 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>
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|  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>
 
|  Formula = PBr<sub>5</sub>
 
|  MolarMass = 430.49 g mol<sup>−1</sup>
 
|  MolarMass = 430.49 g mol<sup>−1</sup>
 
|  Appearance = red-yellow solid
 
|  Appearance = red-yellow solid
|  Density =  
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|  Density = 3.595 g cm<sup>−3</sup>
 
|  Solubility = hydrolyzes
 
|  Solubility = hydrolyzes
 
|  MeltingPt = 83.8 °C
 
|  MeltingPt = 83.8 °C
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|  OtherAnions = [[Phosphorus pentafluoride]]<br />[[Phosphorus pentachloride]]<br/>[[Phosphorus pentaiodide]]
 
|  OtherAnions = [[Phosphorus pentafluoride]]<br />[[Phosphorus pentachloride]]<br/>[[Phosphorus pentaiodide]]
 
|  OtherCations = [[Arsenic pentabromide]]<br/>[[Antimony pentabromide]]<br/>[[Bismuth pentabromide]]
 
|  OtherCations = [[Arsenic pentabromide]]<br/>[[Antimony pentabromide]]<br/>[[Bismuth pentabromide]]
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|  OtherCpds = [[Phosphorus tribromide]]
 
   }}
 
   }}
 
}}
 
}}
'''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 name="Kirk-Othmer"/>
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| Name = Tetrabromophosphonium bromide
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| Section1 = {{Chembox Identifiers
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|  StdInChI=1S/Br4P.BrH/c1-5(2,3)4;/h;1H/q+1;/p-1
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|  StdInChIKey = BVHDGQDJOKBOHK-UHFFFAOYSA-M
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|  CASNo = 7789-69-7
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|  EINECS = 232-186-6
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  }}
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| Section2 = {{Chembox Properties
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|  Formula = PBr{{su|b=4|p=+}}Br<sup>−</sup>
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|  MolarMass = 430.49 g mol<sup>−1</sup>
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  }}
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| Section3 = {{Chembox Structure
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|  Reference = <ref name="Struct"/>
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|  SpaceGroup = P''bcm'' (No. 57)
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|  LattConst_a = 566.3(3) pm
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|  LattConst_b = 1703.1(5) pm
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|  LattConst_c = 824.7(5) pm
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|  Coordination = tetrahedral (P)
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|  MolShape = ''T<sub>d</sub>'': ''r''(P–Br) = 215&nbsp;pm
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  }}
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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&nbsp;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

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 [7789-69-7]
EC number 232-186-6
ChemSpider 56429
Properties[1][2]
Chemical formula PBr5
Molar mass 430.49 g mol−1
Appearance red-yellow solid
Density 3.595 g cm−3
Melting point

83.8 °C

Boiling point

106 °C decomp.

Solubility in water hydrolyzes
Hazards[3]
EU index number not listed
GHS pictograms Skin Corr. 1C, Eye Dam. 1
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
Other compounds Phosphorus tribromide
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Tetrabromophosphonium bromide
Identifiers
Standard InChI InChI=1S/Br4P.BrH/c1-5(2,3)4;/h;1H/q+1;/p-1
Standard InChIKey BVHDGQDJOKBOHK-UHFFFAOYSA-M
CAS number [7789-69-7]
EC number 232-186-6
Properties
Chemical formula PBr+4Br
Molar mass 430.49 g mol−1
Structure[2]
Space group Pbcm (No. 57)
Lattice constant a = 566.3(3) pm, b = 1703.1(5) pm, c = 824.7(5) pm
Coordination geometry tetrahedral (P)
Molecular geometry Td: r(P–Br) = 215 pm
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.[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. 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. 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.
  3. 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.
  4. Greenwood, Norman N.; Earnshaw, A. Chemistry of the Elements; Pergamon: Oxford, 1984; pp 571–75. ISBN 0-08-022057-6.
  5. 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.
  6. Kaslow, C. E.; Marsh, Max M. Substituted Bromoquinolines. J. Org. Chem. 1947, 12 (3), 456–59. DOI: 10.1021/jo01167a014.
  7. 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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