Tris(4-Bromophenyl)Ammoniumyl Hexachloroantimonate

Tris(4-bromophenyl)ammoniumyl hexachloroantimonate
Identifiers
CAS Number	24964-91-8 salt; 37881-41-7 cation;
3D model (JSmol)	Interactive image;
ChemSpider	21493919;
PubChem CID	16688313;
	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-6 Key: SDHBPVANTRLAKE-UHFFFAOYSA-H;
	SMILES C1=CC(=CC=C1[N+](C2=CC=C(C=C2)Br)C3=CC=C(C=C3)Br)Br.Cl[Sb-](Cl)(Cl)(Cl)(Cl)Cl;
Properties
Chemical formula	[(p-BrC; 6H; 4); 3N•]+; [SbCl; 6]−;
Molar mass	816.47 g·mol−1
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 [77 °F], 100 kPa).
	Infobox references

Tris(4-bromophenyl)ammoniumyl hexachloroantimonate is the organic compound with the formula [(4-BrC₆H₄)₃N]SbCl₆.^[1] 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).^[2]

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.^[3]

Related compounds

Magic green, tris(2,4-dibromophenyl)ammoniumyl hexachloroantimonate,^[4]

References

↑ 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 978-0471936237.
↑ 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.
↑ 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. doi:10.1107/S0108270110019748. PMID 20603548.
↑ 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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[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 978-0471936237.

[Geiger-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. doi:10.1107/S0108270110019748. PMID 20603548.

[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.

Identifiers

CAS Number	24964-91-8 salt 37881-41-7 cation
3D model (JSmol)	Interactive image
ChemSpider	21493919
PubChem CID	16688313
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-6 Key: SDHBPVANTRLAKE-UHFFFAOYSA-H
SMILES C1=CC(=CC=C1[N+](C2=CC=C(C=C2)Br)C3=CC=C(C=C3)Br)Br.Cl[Sb-](Cl)(Cl)(Cl)(Cl)Cl
Properties
Chemical formula	[(p-BrC 6H 4) 3N•]+ [SbCl 6]−
Molar mass	816.47 g·mol⁻¹
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 [77 °F], 100 kPa).
Infobox references