Hexaiodobenzene

Hexaiodobenzene
Names
	IUPAC name Hexaiodobenzene
	Other names Periodobenzene
Identifiers
CAS Number	608-74-2;
3D model (JSmol)	Interactive image;
ChemSpider	11360;
ECHA InfoCard	100.009.246
PubChem CID	11853;
CompTox Dashboard (EPA)	DTXSID5060562 ;
	InChI InChI=1S/C6I6/c7-1-2(8)4(10)6(12)5(11)3(1)9 Key: QNMKKFHJKJJOMZ-UHFFFAOYSA-N; InChI=1/C6I6/c7-1-2(8)4(10)6(12)5(11)3(1)9 Key: QNMKKFHJKJJOMZ-UHFFFAOYAO;
	SMILES C1(=C(C(=C(C(=C1I)I)I)I)I)I;
Properties
Chemical formula	C6I6
Molar mass	833.493 g·mol−1
Appearance	orange crystals
Density	4.60 g/cm3
Melting point	430 °C (806 °F; 703 K)
Solubility in water	insoluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Hexaiodobenzene is a chemical compound with the formula C₆I₆. Structurally, it is a derivative of benzene, in which all hydrogen atoms are replaced by iodine atoms. It forms orange crystals^[1] that are poorly soluble in all solvents.

The compound was first prepared by iodination of benzoic acid in the presence of hot fuming sulfuric acid.^[2] It adopts the expected structure with a central C6 ring.^[3]

References

^ ^a ^b ^c Daniell Lewis Mattern: Periodination of Benzene with Periodate/Iodide, J. Org. Chem., 1983, 48 (24), pp. 4772–4773 (doi:10.1021/jo00172a063; PDF).
^ Erwin Rupp "Ueber die perhalogenirten Phtalsäuren und das Hexajodbenzol", Chem. Ber., 1896, Volume 29, pp. 1625–1634 (doi:10.1002/cber.18960290293).
^ Ghosh, Sandip; Reddy, C. Malla; Desiraju, Gautam R. "Hexaiodobenzene: a redetermination at 100 K", Acta Crystallographica, Section E: Structure Reports Online, 2007, 63(2), o910–o911 (doi:10.1107/S1600536807002279).

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[Mattern-1] Daniell Lewis Mattern: Periodination of Benzene with Periodate/Iodide, J. Org. Chem., 1983, 48 (24), pp. 4772–4773 (doi:10.1021/jo00172a063; PDF).

[2] Erwin Rupp "Ueber die perhalogenirten Phtalsäuren und das Hexajodbenzol", Chem. Ber., 1896, Volume 29, pp. 1625–1634 (doi:10.1002/cber.18960290293).

[3] Ghosh, Sandip; Reddy, C. Malla; Desiraju, Gautam R. "Hexaiodobenzene: a redetermination at 100 K", Acta Crystallographica, Section E: Structure Reports Online, 2007, 63(2), o910–o911 (doi:10.1107/S1600536807002279).

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