Isatin
| Names | |
|---|---|
| IUPAC name
1H-Indole-2,3-dione
| |
| Other names
2,3-Dioxo-2,3-dihydroindole
2,3-Diketoindoline 2,3-Dioxindole 2,3-Dioxoindoline 2,3-Indolinedione Indole-2,3-dione o-Aminobenzoylformic anhydride Tribulin | |
| Properties | |
| C8H5NO2 | |
| Molar mass | 147.1308 g/mol |
| Appearance | Orange-red solid |
| Odor | Aromatic, candy-like |
| Density | 1.472 g/cm3[1] |
| Melting point | 189–191 °C (372–376 °F; 462–464 K) [2] |
| Boiling point | Decomposes |
| 0.19 g/100 ml (20 °C) | |
| Solubility | Soluble in acetone, acetonitrile, DMF, DMSO, ethanol, ethyl acetate, methanol, propylene glycol Poorly soluble in diethyl ether, THF, methyl tert-butyl ether, toluene, xylene |
| Vapor pressure | ~0 mmHg |
| Thermochemistry | |
| Std enthalpy of
formation (ΔfH |
251.8 kJ/mol[3] |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
7740 mg/kg (rat, IP) |
| Related compounds | |
| Related compounds
|
Indigo dye |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Isatin, also known as tribulin, is an organic compound with formula C8H5NO2.
Contents
Properties
Chemical
Reaction of isatin with phosphorus pentachloride, followed by reduction with white phosphorus or Zn powder, yields indigo dye.
Dimerization of isatin with potassium borohydride in methanol yields indirubin. This represent the indigo pigment's red component.[4]
The oxidation of isatin using hydrogen peroxide or chromium trioxide yields isatoic anhydride. If peroxydisulfuric acid is used instead, various 1,4‑benzoxazines are obtained.
Physical
Isatin is a reddish-orange solid, almost insoluble in water, but more soluble in some organic solvents. It has a distinct odor, reminiscent of some types of candies.
Availability
Isatin can be bought from chemical suppliers.
Isatin can be found in plants of the genus Isatis[5] (hence its name) as well as in Couroupita guianensis (cannonball tree)[6].
Preparation
Isatin can be prepared by oxidation of indigo dye using nitric acid. Chromic acid can also be used.
The Sandmeyer methodology is the oldest and straightforward way for the synthesis of isatin. This involves the condensation between chloral hydrate and a primary arylamine (e.g. aniline), in the presence of hydroxylamine hydrochloride, in aq. sol. of sodium sulfate to form an α‐isonitrosoacetanilide. Isolation of this intermediate and subsequent electrophilic cyclization promoted by strong acids (e.g. sulfuric acid) furnishes isatin in >75% yield.[7]
Projects
- Make indigo dye
- Red dye
- Compound collecting
Handling
Safety
Isatin appears to have low toxicity. It is known to occur in some plant species.
Storage
In closed bottles
Disposal
No special disposal is required. Can be dumped in trash. Alternatively, it can be turned into indigo blue and disposed off.
References
- ↑ Palenik, Gus J.; Koziol, Anna E.; Katritzky, Alan R.; Fan, Wei-Qiang; Journal of the Chemical Society. Chemical communications; nb. 9; (1990); p. 715 - 716
- ↑ Shiri, Morteza; Salehi, Parvin; Mohammadpour, Zeinab; Salehi, Peyman; Notash, Behrouz; Synthesis; vol. 53; nb. 6; (2021); p. 1149 - 1156
- ↑ Matos, M. Agostinha R.; Miranda, Margarida S.; Morals, Victor M.F.; Liebman, Joel F.; Organic and Biomolecular Chemistry; vol. 1; nb. 14; (2003); p. 2566 - 2571
- ↑ Wang, Cuiling; Yan, Jiaxu; Du, Mo; Burlison, Joseph A.; Li, Chi; Sun, Yanni; Zhao, Danqing; Liu, Jianli (May 2017). "One step synthesis of indirubins by reductive coupling of isatins with KBH 4". Tetrahedron. 73 (19): 2780–2785
- ↑ Jue Zhou, July 2011, African Journal of Traditional, Complementary and Alternative Medicines 8(5 Suppl):33-45, "Analysis of the extracts of Isatis tinctoria by new analytical approaches of HPLC, MS AND NMR"
- ↑ Rahul R. Tripathi, September 2013, International Letters of Chemistry Physics and Astronomy 15:119-12, "An Extraction of the Isatin from the Couroupita guianesis (Cannon Ball Tree) and a Novel Synthesis of the N,N'-(2-oxo-3'H-spiro[indoline-3,2'-[1,3,4thiadiazole]-3',5'-diyl]diacetamidefrom the Isatin"]
- ↑ https://zenodo.org/records/1426793
