| Isatin | Isatin, is also known as indenedione, indole quinone. Its chemical name is indol(o)-2,3-dione,it is orange-red monoclinic prism crystal at room temperature. Bitter. The molecular weight is147.13. Melting point 203.5 ℃ (Part sublimation). Dissolved in water, hot ethanol, benzene, acetone, ether-soluble. Soluble in boiling alcohol, soluble in ether and boiling water and it is reddish brown , soluble in caustic and solution is purple, it changes to yellow after placement. Its alcohol solution has a very unpleasant odor. Weakly alkaline, it can salify with a perchlorate.
Above information of is edited by Andy from ChemicalBook (2016-11-19). |
| Chemical Properties | Orange-red monoclinic prism crystals. Melting point 203.5 ℃ (Part sublimation). Soluble in hot ethanol, ethyl ether-soluble, soluble in hot water, benzene, acetone, dissolved in alkali metal hydroxide oxide. The solution is purple, it turns yellow after placement, alkaline activity is extremely weak. Bitter. |
| Uses | (1) The product is used as medicine and dye intermediates ,and it is used for the production of drug quinophan, dye disperse Yellow E-3G ; in chemical analysis,it is used as reagents for the determination of copper ions, mercaptans, thiophene, indoxyl-beta-glucoside.
(2) Isatin as a reference material for the preparation of indigo and Maya blue; for the preparation of phthalazinone derivatives, spirooxindole derivatives, the expression of P-glycoprotein for multi-drug resistant cells; The ketone is fused to form indole-2-one as a tubercular mycobacterial protein tyrosine phosphatase B, a potent selective inhibitor, as a powerful antimicrobial and antifungal triazole-isatine complex, And the Knoevenagel enrichment reaction; the isatin is activated by the direct sp2/sp3C-H bond, and undergoes a reaction with the cyclopentadienyl-Pd (II) catalyzes the CH addition reaction to form 3-substituted-3-hydroxy 2-oxindole. |
| production method | Condensation of chloral and aniline can generate oximide-acetanilide, and then by cyclization, hydrolysis , isatin is obtained. |
| Chemical Properties | orange-red powder or crystals |
| Uses | manufacture of vat dyes. In analytical chemistry as a reagent for cuprous ions, mercaptans, thiophene, and indican. |
| Uses | Isatin is an endogenous monoamine oxidize (MAO) inhibitor involved in stress and anxiety. Additionally, isatin inhibits alkaline phosphatase (ALP), nitric oxide (NO)-stimulated soluble guanylate cyclase, and other enzymes. Isatins undergo a one-pot Wolff-Kishner like reduction with hydrazine hydrate, under surprisingly mild conditions, to give the corresponding oxindoles. It is used as chromatographic spray reagent for amino acid detection. |
| Uses | Isatin can be used as a reactant to prepare:
Phthalazinone derivatives. Spirooxindole derivatives. Agents against multidrug-resistant cells expressing P-glycoprotein. Thiazolidinones spiro-fused to indolin-2-ones as potent and selective inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B. Triazole-isatine compounds as potential antibacterial and antifungal agents. Biologically relevant scaffolds such as spiro[indole-thiazolidinones].
It can be a reactant for:
Isatin can also be used as a chromatographic spray reagent for amino acids, and also as a reference material in the preparation of indigo and Maya Blue. It is responsible for the yellow color exhibited by the "Maya Yellow" pigment. |
| Definition | ChEBI: An indoledione that is the 2,3-diketo derivative of indole. |
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