Indoxyl
Chemical compound
From Wikipedia, the free encyclopedia
In organic chemistry, indoxyl is a nitrogenous substance with the chemical formula: C8H7NO.[1][2] Indoxyl is isomeric with oxindol and is obtained as an oily liquid.
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| Names | |
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| Preferred IUPAC name
1H-Indol-3-ol | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.216.308 |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C8H7NO | |
| Molar mass | 133.14728 |
| Hazards | |
| GHS labelling: | |
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| Danger | |
| H302, H311, H319, H400 | |
| P264, P270, P273, P280, P301+P312, P302+P352, P305+P351+P338, P312, P322, P330, P337+P313, P361, P363, P391, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation
The Heumann indigo synthesis starts from anthranilic acid:
Indoxyl-Synthese: Anthanilic acid (1) reacts with chloroacetic acid to give phenylglycine-o-carboxylic acid. When treated in molten sodium carbonate, the 2-Indoxycarboxylic acid (3) decarboxylates to give indoxyl (4) .
In nature indoxyl is derived from indican, which is a glycoside. The hydrolysis of indican yields β-D-glucose and indoxyl.
Indigo dye is a product of the mild oxidation of indoxyl.
Indoxyl can be found in urine and is titrated with Obermayer's reagent, which is a dilute solution of ferric chloride (FeCl3) in hydrochloric acid (HCl).[3]
