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1 article(s) from Concepcion, Julie

A new synthesis of Tyrian purple (6,6’-dibromoindigo) and its corresponding sulfonate salts

Holly Helmers,
Mark Horton,
Julie Concepcion,
Jeffrey Bjorklund and
Nicholas C. Boaz

Beilstein J. Org. Chem. 2026, 22, 167–174, doi:10.3762/bjoc.22.10

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Scheme 1: A) Generalized synthetic scheme for several previous syntheses of 6,6’-dibromoindigo. B) The synthe...

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Scheme 2: Synthetic scheme for the preparation of 6,6’-dibromoindigo from p-bromotoluene (5).

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Scheme 3: Nitration of p-bromotoluene (5) yields a mixture of regioisomers 3 and 7.

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Scheme 4: Benzylic bromination of 4-bromo-2-nitrotoluene (3).

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Scheme 5: A) Treatment of 4-bromo-2-nitrobenzyl bromide (6) with DMSO did not yield the alkoxysulfonium ion i...

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Scheme 6: Condensation of 4-bromo-2-nitrobenzaldehyde (4) to yield 6,6’-dibromoindigo (1).

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Scheme 7: A) Disulfonation of 6,6’-dibromoindigo (1), to yield 6,6’-dibromo-5,5’-indigodisulfonic acid disodi...

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Figure 1: A) UV–vis spectra of 6,6’-dibromo-5,5’,7-indigotrisulfonic acid trisodium salt (10) (10 μM) in aque...

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Published 21 Jan 2026

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