ChemicalBook CAS DataBase List 6-Carboxyfluorescein

6-Carboxyfluorescein synthesis

2synthesis methods

Product Name:6-Carboxyfluorescein
CAS Number:3301-79-9
Molecular formula:C21H12O7
Molecular Weight:376.32

1,2,4-Benzenetricarboxylic anhydride (also called 4- carboxyphthalic anhydride, 25.0 g, 0.13 mol) was added to a solution of 1,3-dihydroxybenzene (also called resorcinol, 28.6 g, 0.26 mol) in methane sulfonic acid (1M). An air condenser was attached to the flask and the reaction was heated at 85 oC in an open vessel for 24 h. After cooling to room temperature, the reaction mixture was poured into 7 volumes of ice/water. An orange-yellow precipitate formed; this was collected by filtration and dried in an oven at 200 oC. This residue was recrystallized two times from methanol/hexane to give 1.0 g of 6- carboxyfluorescein methanesulfonic acid adduct preferentially crystallizes from MeOH/hexanes. The mother liquors from this procedure were collected, the solvent was removed in vacuo, and the residues were recrystallized two times from ethanol/hexanes to give 3.2 g of 5-carboxyfluorescein methanesulfonic acid adduct preferentially crystallizes from EtOH/hexanes. Finally, the mother liquors from this experiment were combined, evaporated to dryness, and recrystallized two times from methanol/hexanes to give another 3.0 g of 6-carboxyfluorescein methanesulfonic acid adduct preferentially crystallizes from MeOH/hexanes, making a total yield of 4.0 g, 40 %. Careful dropwise addition of conc. HCl(aq) to solutions of these methanesulfonic esters preferentially crystallizes from EtOH/hexanes and preferentially crystallizes from MeOH/hexanes in 4M sodium hydroxide gave 5-carboxyfluorescein and 6-carboxyfluorescein, respectively in near quantitative yield.

108-46-3 Synthesis

108-46-3
747 suppliers
$10.00/10g

552-30-7
401 suppliers
$16.00/25g

3301-79-9
226 suppliers
$49.00/100mg

76823-03-5 Synthesis

76823-03-5
249 suppliers
$13.00/25mg

Yield:-

Reaction Conditions:

with sulfuric acid at 130; for 0.04 h;Irradiation;Title compound not separated from byproducts;

References:

El'tsov, A. V.;Martynova, V. P.;Sokolova, N. B.;Dmitrieva, N. M.;Brykov, A. S [Russian Journal of General Chemistry,1995,vol. 65,# 3.2,p. 454 - 456][Zhurnal Obshchei Khimii,1995,vol. 65,# 3,p. 511 - 513]

100-44-7 Synthesis

100-44-7
625 suppliers
$13.50/250G

108-46-3 Synthesis

108-46-3
747 suppliers
$10.00/10g

552-30-7
401 suppliers
$16.00/25g

3301-79-9
226 suppliers
$49.00/100mg

76823-03-5 Synthesis

76823-03-5
249 suppliers
$13.00/25mg

References

6-Carboxyfluorescein Related Search:

Fluorescein 5-Carboxyfluorescein 6-CARBOXYFLUORESCEIN DIACETATE 5-CARBOXYFLUORESCEIN DIACETATE 6-CARBOXYFLUORESCEIN N-SUCCINIMIDYL ESTER 5,6-CARBOXYFLUORESCEIN DIPIVALATE