Sulfuric Acid → Sodium 3-hydroxypyrene-5-sulfonate

Participants

Reaction Steps

The synthesis of mono-CysMA is given in Scheme 1. Reaction of HPTS with 30% sulfuric acid at 150° C. for 20 min gave sodium 3-hydroxypyrene-5-sulfonate 1 in 10% yield. Acetylation of 1 followed by chlorination of 2 gave intermediate 3. The polymerizable group was attached via the cysteic acid moiety in compound 4 and reacted with 3 to give compound 5. Chlorosulfonation of 5 was achieved without affecting the polymerizable group and after purification on polystyrene beads gave mono-CysMA in 50% yield over two steps. The dye was characterized by 1H NMR, HPLC, and MS.

Provenance & Evidence