Synthesis of eosin (3,4,5,6-tetrabromofluorescein)

Preparation of eosin (3,4,5,6-tetrabromofluorescein)

Preparation of eosin

Preparation of eosin

To a 200 ml three-necked round bottom flask equipped with a mechanical stirrer, thermometer and addition funnel, 100 ml of ethanol and 16.6 g (0.05 mole) of pure fluorescein were placed. With constant stirring 36 g (0.45 mol) of bromine were added. During the addition  the heat was evolved and reaction must be controlled so that the temperature did not exceed 40° C. After the introduction of half of the bromine precipitate of fluorescein disappears as dibromfluorescein forms readily soluble in alcohol. During the further addition of bromine gradually crystals of 3,4,5,6-tetrabromofluorescein (eosin) were obtained. To complete the reaction after addition of bromine the mixture was stirred for another 15 minutes and then allowed to crystallize for a day. The separated crystals are filtered on a Buchner funnel and washed with 20 ml of alcohol. Crystal eosin contains 1 part alcohol. For removal of the alcohol eosin is dried at a temperature of 110 ° C. Yield 30 g (92% of theory).

Препаративная органическая химия, Вульфсон Н.С., 199-200, 1959 (Preparative organic chemistry, Wolfson N. S., 199-200, 1959)

IUPAC Name

2,3,4,5-tetrabromo-6-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid

InChI

InChI=1S/C20H8Br4O5/c21-16-14(15(20(27)28)17(22)19(24)18(16)23)13-9-3-1-7(25)5-11(9)29-12-6-8(26)2-4-10(12)13/h1-6,25H,(H,27,28)

InChI Key

MQGBYISSPZLIEZ-UHFFFAOYSA-N

Canonical SMILES

C1=CC2=C(C=C1O)OC3=CC(=O)C=CC3=C2C4=C(C(=C(C(=C4Br)Br)Br)Br)C(=O)O

Depositor-Supplied Synonyms

3,4,5,6-tetrabromofluorescein, Protein Synthesis Initiation Inhibitor, NSC 119889, AC1L5HSW, CTK7H3559, HSCI1_000115, NSC122393, NSC-122393, BRD-K59637651-001-01-4, 2,3,4,5-tetrabromo-6-(3-hydroxy-6-oxo-xanthen-9-yl)benzoic acid, 2,3,4,5-tetrabromo-6-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid, 2,3,4,5-tetrabromo-6-(6-hydroxy-3-oxo-3h-xanthen-9-yl)benzoic acid, Benzoic acid, 2,3,4,5-tetrabromo-6-(6′-hydroxy-3′-oxo-3H-xanthen-9′-yl)-

Removed Synonyms

Tetrabromofluorescein, CID275510

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