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Chemical Structure| 59-48-3 Chemical Structure| 59-48-3
Chemical Structure| 59-48-3

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Oxindole is an aromatic heterocyclic organic compound which causes sedation, muscle weakness, hypotension, and coma when dosed in excess.

Synonyms: 2-Indolinone; NSC 274863; Indolin-2-one

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Product Details of Oxindole

CAS No. :59-48-3
Formula : C8H7NO
M.W : 133.15
SMILES Code : O=C1NC2=C(C=CC=C2)C1
Synonyms :
2-Indolinone; NSC 274863; Indolin-2-one
MDL No. :MFCD00005711
InChI Key :JYGFTBXVXVMTGB-UHFFFAOYSA-N
Pubchem ID :321710

Safety of Oxindole

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of Oxindole

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 59-48-3 ]
  • Downstream synthetic route of [ 59-48-3 ]

[ 59-48-3 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 59-48-3 ]
  • [ 459-57-4 ]
  • [ 3476-86-6 ]
YieldReaction ConditionsOperation in experiment
85% With piperidine In ethanol at 90℃; Inert atmosphere General procedure: The appropriate aldehyde (1 equiv) was added to EtOH (3 mL/0.2 mmol) and the mixture was stirred until complete solution. Theoxindole (1 equiv) and piperidine (0.1 equiv) were added, and themixture was heated to 90°C for 3-7 h, and cooled. The resultingprecipitatewas filtered, washed with cold ethanol and dried to givethe pure compound. If necessary, additional recrystallization inethanol was applied to obtain the pure product.
References: [1] European Journal of Medicinal Chemistry, 2017, vol. 130, p. 286 - 307.
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 5, p. 2077 - 2090.
[3] Journal of Chemical Research, 2018, vol. 42, # 5, p. 244 - 246.
  • 2
  • [ 59-48-3 ]
  • [ 459-57-4 ]
  • [ 3476-86-6 ]
  • [ 90828-17-4 ]
YieldReaction ConditionsOperation in experiment
25% With piperidine In ethanol for 3 h; Reflux General procedure: The preparation of compounds 3-25 was carried out by refluxing oxindole with different aromatic aldehydes in ethanol in the presence of a catalytic amount of piperidine were refluxed for 3 h. After cooling reaction mixture was concentrated at reduced pressure to obtain solid of 3-oxindole derivatives, then washed with 1:1 mixture of hexane-ethyl acetate (25 mL) and dried to afford titles compoundsin good yields (Table 1). Only in two cases (10 and21), both E and Z isomers were obtained, these isomers wereseparated by column chromatography using 1:9 ethyl acetate: hexane as eluent. The structures of synthetic compounds 3-25 were elucidated by 1H NMR and EI MS. Elemental analysis results were also found to be satisfactory.
References: [1] Medicinal Chemistry, 2013, vol. 9, # 5, p. 681 - 688.
  • 3
  • [ 59-48-3 ]
  • [ 142273-20-9 ]
References: [1] European Journal of Organic Chemistry, 2012, # 5, p. 1019 - 1024.
  • 4
  • [ 59-48-3 ]
  • [ 6287-38-3 ]
  • [ 114727-43-4 ]
References: [1] Heterocyclic Communications, 2008, vol. 14, # 4, p. 263 - 267.
[2] European Journal of Medicinal Chemistry, 1992, vol. 27, # 8, p. 779 - 789.
  • 5
  • [ 59-48-3 ]
  • [ 252882-61-4 ]
References: [1] Patent: US6172076, 2001, B2, .
[2] Patent: WO2008/144266, 2008, A1, .
[3] Patent: US2008/306102, 2008, A1, .
 

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