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Tris(4-bromophenyl)ammoniumyl hexachloroantimonate

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Tris(4-bromophenyl)ammoniumyl hexachloroantimonate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
InChI
  • InChI=1S/C18H12Br3N.6ClH.Sb/c19-13-1-7-16(8-2-13)22(17-9-3-14(20)4-10-17)18-11-5-15(21)6-12-18;;;;;;;/h1-12H;6*1H;/q+1;;;;;;;+5/p-6Key: SDHBPVANTRLAKE-UHFFFAOYSA-H
SMILES
  • C1=CC(=CC=C1(C2=CC=C(C=C2)Br)C3=CC=C(C=C3)Br)Br.Cl(Cl)(Cl)(Cl)(Cl)Cl
Properties
Chemical formula [(p-BrC6H4)3N•][SbCl6]
Molar mass 816.47 g·mol
Appearance blue solid
Melting point 141 to 142 °C (286 to 288 °F; 414 to 415 K)
Solubility in water acetonitrile
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Tris(4-bromophenyl)ammoniumyl hexachloroantimonate is the organic compound with the formula SbCl6. Commonly known as magic blue, it is the hexachloroantimonate salt of an amine radical cation. It is a blue solid that reacts with many solvents but is soluble in acetonitrile. The compound is a popular oxidizing agent in organic and organometallic chemistry, with a reduction potential of 0.67 V versus ferrocene/ferrocenium (acetonitrile solution) or 0.70 V versus ferrocene/ferrocenium (dichloromethane solution).

The structure of the cation consists of a three-bladed propeller structure with a planar amine. It is nearly identical to the parent triphenylamine. The weakly coordinating anion is SbCl
6, which is octahedral.

Related compounds

  • Magic green, tris(2,4-dibromophenyl)ammoniumyl hexachloroantimonate,

References

  1. Earle, Martyn J.; Vibert, Aude; Jahn, Ullrich (2011). "Tris(4-bromophenyl)aminium Hexachloroantimonate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt397.pub2. ISBN 978-0-471-93623-7.
  2. Connelly, N. G.; Geiger, W. E. (1996). "Chemical Redox Agents for Organometallic Chemistry". Chem. Rev. 96 (2): 877–910. doi:10.1021/cr940053x. PMID 11848774.
  3. Quiroz-Guzman, Mauricio; Brown, Seth N. (2010). "Tris(4-bromophenyl)aminium hexachloridoantimonate ('Magic Blue'): A strong oxidant with low inner-sphere reorganization". Acta Crystallographica Section C. 66 (7): m171 – m173. Bibcode:2010AcCrC..66M.171Q. doi:10.1107/S0108270110019748. PMID 20603548.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. Schmidt, Werner; Steckhan, Eberhard (1980). "Über organische Elektronenüberträgersysteme, I. Elektrochemische und spektroskopische Untersuchung bromsubstituierter Triarylamin-Redoxsysteme". Chemische Berichte. 113 (2): 577–585. doi:10.1002/cber.19801130215.
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