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5(6)-Nitrofluorescein

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5(6)-Nitrofluorescein Basic information

Product Name:
5(6)-Nitrofluorescein
Synonyms:
  • 5(6)-Nitrofluorescein
  • 3',6'-Dihydroxy-5(or 6)-nitro-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one
  • 3',6'-Dihydroxy-5(or 6)-nitro-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one
CAS:
78512-32-0
MF:
C20H11NO7
MW:
377.30384
Mol File:
78512-32-0.mol
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5(6)-Nitrofluorescein Chemical Properties

storage temp. 
2-8°C
InChI
InChI=1S/C20H11NO7/c22-11-2-5-15-17(8-11)27-18-9-12(23)3-6-16(18)20(15)14-4-1-10(21(25)26)7-13(14)19(24)28-20/h1-9,22-23H
InChIKey
UACQOMKZFGNRBL-UHFFFAOYSA-N
SMILES
O1C2(C3=C(C=C(O)C=C3)OC3=C2C=CC(O)=C3)C2=CC=C([N+]([O-])=O)C=C2C1=O
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5(6)-Nitrofluorescein Usage And Synthesis

Uses

5(6)-Nitrofluorescein is the mixture of 5- and 6-nitrofluoresceine isomers. This compound is a useful compound that could be used to synthesize fluorescein 5-isothiocyanate.

Synthesis

A process for the preparation of a mixture (5(6)-Nitrofluorescein) of 3′,6′-dihydroxy-6-nitrospiro[2-benzofuran-3,9′-xanthene]-1-one and 3′,6′-dihydroxy-5-nitrospiro[2-benzofuran-3,9′- xanthene]-1-one comprising the steps of (a) reacting 4-nitrophthalic acid or 4-nitrophthalic anhydride with benzene-1,3-diol in methanesulphonic acid; (b) quenching the reaction in step (a) with a solvent to precipitate product; (c) isolating the precipitate; (d) heating the precipitate in water in order to hydrolyse any methansulphonic acid ester present.

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