114618
Isatin
97%
Synonym(s):
2,3-Diketoindoline, 2,3-Dioxo-2,3-dihydroindole, 2,3-Dioxoindoline, o-Aminobenzoylformic anhydride, Isatic acid lactam, Isatinic acid anhydride, 2,3-Indolinedione, Isatine, NSC 9262
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About This Item
Empirical Formula (Hill Notation):
C8H5NO2
CAS Number:
Molecular Weight:
147.13
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
202-077-8
Beilstein/REAXYS Number:
383659
MDL number:
Assay:
97%
Form:
powder
Quality Segment
assay
97%
form
powder
mp
193-195 °C (dec.) (lit.)
solubility
boiling water: soluble, diethyl ether: soluble, soluble
functional group
ketone
SMILES string
O=C1Nc2ccccc2C1=O
InChI
1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)
InChI key
JXDYKVIHCLTXOP-UHFFFAOYSA-N
Application
Isatin can be used as a reactant to prepare:
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.
- 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:
- Cascade reactions with heterocyclic ketene aminals.
- Knoevenagel condensation reactions.
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.
Isatin undergoes Pd(II)-catalyzed C-H addition by direct sp2/sp3 C-H bond activation to form 3-substituted-3-hydroxy-2-oxindoles. Isatin derivatives (bis-Schiff base) are synthesized by the condensation of the natural or synthetic isatins with hydrazine.
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Storage Class
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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