6,6'-Dibromoindigo

6,6'-Dibromoindigo
Names
	Other names 6BrIG; Tyrian purple
Identifiers
CAS Number	1277170-99-6;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:80914;
ChemSpider	4590500;
KEGG	C17084;
PubChem CID	177057;
UNII	2O3DDL8TAF;
CompTox Dashboard (EPA)	DTXSID801314818 ;
	InChI InChI=1S/C16H8Br2N2O2/c17-7-1-3-9-11(5-7)19-13(15(9)21)14-16(22)10-4-2-8(18)6-12(10)20-14/h1-6,19,21H; Key: UOZOCOQLYQNHII-UHFFFAOYSA-N;
	SMILES C1=CC2=C(C=C1Br)NC(=C2O)C3=NC4=C(C3=O)C=CC(=C4)Br;
Properties
Chemical formula	C16H8Br2N2O2
Molar mass	420.060 g·mol−1
Appearance	purple solid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

6,6'-Dibromoindigo is an organic compound with the formula (BrC₆H₃C(O)CNH)₂. A deep purple solid, the compound is also known as Tyrian purple, a dye of historic significance. Presently, it is only a curiosity, although the related derivative indigo is of industrial significance. The molecule consists of a pair of monobrominated indole rings linked by a carbon-carbon double bond. It is produced by molluscs of the Muricidae species.^[1]

The pure compound has semiconductor properties in the thin film phase, which is potentially useful for wearable electronics, and has better performance than the parent indigo in this context.^[2]^[3]

^ McGovern, Patrick E.; Michel, R. H. (1990). "Royal Purple dye: The chemical reconstruction of the ancient Mediterranean industry". Accounts of Chemical Research. 23 (5): 152–158. doi:10.1021/ar00173a006.
^ Pandolfi, Lorenzo; Rivalta, Arianna; Salzillo, Tommaso; Giunchi, Andrea; D’Agostino, Simone; Della Valle, Raffaele G.; Brillante, Aldo; Venuti, Elisabetta (13 August 2020). "In Search of Surface-Induced Crystal Structures: The Case of Tyrian Purple". The Journal of Physical Chemistry C. 124 (32): 17702–17710. doi:10.1021/acs.jpcc.0c05186. hdl:11585/786088.
^ "Tyrian purple: The lost ancient pigment that was more valuable than gold". www.bbc.com.

[1] McGovern, Patrick E.; Michel, R. H. (1990). "Royal Purple dye: The chemical reconstruction of the ancient Mediterranean industry". Accounts of Chemical Research. 23 (5): 152–158. doi:10.1021/ar00173a006.

[2] Pandolfi, Lorenzo; Rivalta, Arianna; Salzillo, Tommaso; Giunchi, Andrea; D’Agostino, Simone; Della Valle, Raffaele G.; Brillante, Aldo; Venuti, Elisabetta (13 August 2020). "In Search of Surface-Induced Crystal Structures: The Case of Tyrian Purple". The Journal of Physical Chemistry C. 124 (32): 17702–17710. doi:10.1021/acs.jpcc.0c05186. hdl:11585/786088.

[3] "Tyrian purple: The lost ancient pigment that was more valuable than gold". www.bbc.com.

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