2,3-dihydro-1H-indole-2,3-dione

• ChemBase ID: 1858
• Molecular Formular: C8H5NO2
• Molecular Mass: 147.1308
• Monoisotopic Mass: 147.03202841
• SMILES: O=C1Nc2ccccc2C1=O
• Canonical SMILES: O=C1C(=O)Nc2c1cccc2
• InChI: InChI=1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)
• InChIKey: JXDYKVIHCLTXOP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dihydro-1H-indole-2,3-dione
• IUPAC Traditional name: isatin
• Synonyms: Indole-2,3-dione; 2,3-Indolinedione; 2,3-Indolinedione; 2,3-Dioxo-2,3-dihydroindole; 2,3-Diketoindoline; 2,3-Dioxoindoline; o-Aminobenzoylformic anhydride; Isatic acid lactam; Isatine; Isatinic acid anhydride; NSC 9262; Isatin; indoline-2,3-dione; 1H-indole-2,3-dione; Isatin; 吲哚-2,3-二酮; 靛红

Database IDs

• CAS Number: 91-56-5
• EC Number: 202-077-8
• MDL Number: MFCD00005718
• Beilstein Number: 383659
• Merck Index: 145104
• PubChem SID: 24881078; 160965313; 24847187; 46507369
• PubChem CID: 7054
• CHEBI ID: 27539
• CHEMBL: 326294
• Chemspider ID: 6787
• DrugBank ID: DB02095
• KEGG ID: C11129
• Wikipedia Title: Isatin

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.925315
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.6013886
• LogD (pH = 7.4): 1.5894221
• Log P: 1.6015435
• Molar Refractivity: 40.475 cm^3
• Polarizability: 14.544493 Å^3
• Polar Surface Area: 46.17 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.89
• LOG S: -1.72
• Solubility (Water): 2.77e+00 g/l

PROPERTIES

Physical Property

• Apperance: Orange-red solid
• Melting Point: 193-195 °C (dec.)(lit.); 195-200°C (dec.); 200°C; 201-203 °C; ca 194°C dec.
• Flash Point: 220°C(428°F)
• Hydrophobicity(logP): 0.83 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: NL7873000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36/37/38; R22 R36 R37 R38
• Safety Statements: 26-36
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.5%; ≥99.0%; ≥99.0% (NT); 95+%; 98%
• Grade: JIS special grade
• Ignition Residue: ≤0.1%
• Loss on Drying: ≤0.5% loss on drying
• Quality: for spectrophotometric det. of proline and thiophene
• Empirical Formula (Hill Notation): C8H5NO2
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 02102071

Crystalline
Chromatographic spray reagent for amino acid detection.

MP Biomedicals - 05205070

MP Biomedicals Rare Chemical collection

DrugBank - DB02095

• Drug Groups: experimental
• Description: Isatin is an indole derivative. The compound was first obtained by Erdman and Laurent in 1841 as a product from the oxidation of Indigo dye by nitric acid and chromic acids. The compound is found in many plants and Schiff bases of Isatin are investigated for their pharmaceutical properties. [Wikipedia]
• External Links: Wikipedia

Sigma Aldrich - 114618

Packaging
100, 500 g in poly bottle
5 g in glass bottle
Application
Reactant for preparation of:
• Phthalazinone derivatives1
• Spirooxindole derivatives2
• Agents against multidrug-resistant cells expressing P-glycoprotein3
• Thiazolidinones spiro-fused to indolin-2-ones as potent and selective inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B4
• Triazole-isatine compounds as potential antibacterial and antifungal agents5
• Biologically relevant scaffolds such as spiro[indole-thiazolidinones]6Reactant for:
• Cascade reactions with heterocyclic ketene aminals7
• Knoevenagel condensation reactions8

Sigma Aldrich - 58240

Other Notes
Reagent for the spectrophotometric det. of thiophene and proline1

REFERENCES

• Isatins undergo a one-pot Wolff-Kishner like reduction with hydrazine hydrate, under surprisingly mild conditions, to give the corresponding oxindoles: Synth. Commun., 24, 2835 (1994).
• Reaction with acid anhydrides or condensation with 4-Methyl-2-pentanone, A11618, results in the formation of quinoline-4-carboxylic acid derivatives; for examples, see: J. Med. Chem., 35, 4893 (1992); 36, 617, 3286 (1993).: