Indoxyl

Indoxyl

Skeletal formula
Names
Preferred IUPAC name 1H-Indol-3-ol
Identifiers
CAS Number	480-93-3 checkY
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17840 checkY
ChemSpider	45861 checkY
ECHA InfoCard
EC Number	689-424-0
E number
KEGG	C05658 checkY
PubChem CID	50591
UNII	BZ24HY3WPJ checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C8H7NO/c10-8-5-9-7-4-2-1-3-6(7)8/h1-5,9-10H checkY Key: PCKPVGOLPKLUHR-UHFFFAOYSA-N checkY InChI=1/C8H7NO/c10-8-5-9-7-4-2-1-3-6(7)8/h1-5,9-10H Key: PCKPVGOLPKLUHR-UHFFFAOYAR
SMILES Oc2c1ccccc1[nH]c2
Properties
Chemical formula	C8H7NO
Molar mass	133.14728
Hazards
GHS labelling:
Pictograms	GHS06: ToxicGHS09: Environmental hazard
Signal word	Danger
Hazard statements	H302, H311, H319, H400
Precautionary statements	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). checkY verify (what is checkY☒N ?) Infobox references

In organic chemistry, indoxyl is a nitrogenous substance with the chemical formula: C₈H₇NO. Indoxyl is isomeric with oxindol and is obtained as an oily liquid.

Preparation

The Heumann indigo synthesis starts from anthranilic acid:

File:Synthesis Indoxyl.svg

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).