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Key Documents

O9808

Sigma-Aldrich

2-Oxindole

97%

Synonym(s):

2-Indolinone, Oxindole

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About This Item

Empirical Formula (Hill Notation):
C8H7NO
CAS Number:
Molecular Weight:
133.15
Beilstein:
114692
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

crystals

bp

227 °C/73 mmHg (lit.)

mp

123-128 °C (lit.)

SMILES string

O=C1Cc2ccccc2N1

InChI

1S/C8H7NO/c10-8-5-6-3-1-2-4-7(6)9-8/h1-4H,5H2,(H,9,10)

InChI key

JYGFTBXVXVMTGB-UHFFFAOYSA-N

Gene Information

human ... PGR(5241)

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Organic letters, 13(1), 82-85 (2010-12-09)
The first tertiary amine catalyzed enantioselective Morita-Baylis-Hillman (MBH) reaction of isatins with acrylates has been demonstrated, allowing asymmetric synthesis of biologically significant 3-substituted-3-hydroxy-2-oxindoles in good yields and with excellent enantioselectivities. The C6'-OH group of β-isocupreidine (β-ICD) is believed to facilitate
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An efficient palladium-catalyzed protocol for the synthesis of 3-arylidene-2-oxindoles has been developed. In this approach, a sequential one-pot six-component reaction via Ugi/Heck carbocyclization/Sonogashira/nucleophilic addition was used for the synthesis of the desired skeleton.
Xianjie Chen et al.
Organic letters, 15(8), 1846-1849 (2013-04-09)
An asymmetric organo- and gold-catalyzed one-pot sequential Mannich/hydroamination reaction has been developed. Using this protocol, spiro[pyrrolidin-3,2'-oxindole] derivatives were synthesized in good yields (up to 91%) and excellent enantioselectivities (up to 97% ee).
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Bioorganic & medicinal chemistry, 18(13), 4674-4686 (2010-06-24)
A series of new ureidoindolin-2-one derivatives were synthesized and evaluated as inhibitors of receptor tyrosine kinases. Investigation of structure-activity relationships at positions 5, 6, and 7 of the oxindole skeleton led to the identification of 6-ureido-substituted 3-pyrrolemethylidene-2-oxindole derivatives that potently

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