Standard Article

Oxindole; Isatin; 1H-Indole-2,3-dione

  1. Elisa G. Gutierrez,
  2. Annaliese K. Franz

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rn01611

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Gutierrez, E. G. and Franz, A. K. 2013. Oxindole; Isatin; 1H-Indole-2,3-dione. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. University of California, Davis, CA, USA

Publication History

  1. Published Online: 16 SEP 2013

Chemistry Terms

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Abstract

(reagent used primarily as an electrophilic component in a wide array of reactions)

Physical Data: mp 193–195 °C1; 202–203 °C.2

Solubility: Slightly soluble in water. Soluble in polar organic solvents such as methanol, acetone, DMSO, DMF, acetonitrile, or ethyl acetate. Partially soluble in organic solvents such as CH2Cl2 or CHCl3. Not soluble in nonpolar organic solvents such as hexanes, benzene, and toluene.

Form Supplied in: orange solid; commercially available.

Analysis of Reagent Purity:1H NMR spectroscopy.3

Handling, Storage, and Precautions: Shelf stable. Eye and skin irritant. Intraperitoneal LD50 (rat) is 7.740 mg kg−1.4

Preparative Methods: Sandmeyer isatin synthesis is the most well-established and frequently-used preparative method for the synthesis of 2,3-indolinedione (isatin).5 In this method, aniline 1 undergoes condensation with chloral hydrate and hydroxylamine hydrochloride in aqueous sodium sulfate to form an isonitrosoacetanilide 2. The isonitrosoacetanilide 2 cyclizes upon exposure to concentrated sulfuric acid and the crystalline isatin 3 is collected by filtration (eq 1). The Sandmeyer isatin synthesis is also applicable to anilines with electron-withdrawing substituents.6 New preparative methods for isatin and isatin derivatives continue to be reported, such as the oxidation of indoles to isatins,7 the isolation of isatin from Comamonas sp.,8 and the palladium-catalyzed preparation of isatins from nitrobenzenes.9

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Featured Compounds

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Compound Information
Molecular Weight:147.1308
Molecular Formula:C8H5NO2
InChIKey:JXDYKVIHCLTXOP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:93.1265
Molecular Formula:C6H7N
InChIKey:PAYRUJLWNCNPSJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:165.403
Molecular Formula:C2H3Cl3O2
InChIKey:Not Available
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Compound Information
Molecular Weight:164.1613
Molecular Formula:C8H8N2O2
InChIKey:UFNDNNCDEFJCHU-RMKNXTFCSA-N
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Compound Information
Molecular Weight:69.491
Molecular Formula:ClH4NO
InChIKey:WTDHULULXKLSOZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.042
Molecular Formula:Na2O4S
InChIKey:PMZURENOXWZQFD-UHFFFAOYSA-L
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Compound Information
Molecular Weight:98.078
Molecular Formula:H2O4S
InChIKey:QAOWNCQODCNURD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:RPUSRLKKXPQSGP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:251.323
Molecular Formula:C17H17NO
InChIKey:IORPUVWDPYMFES-UHFFFAOYSA-N
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Compound Information
Molecular Weight:107.123
Molecular Formula:C6H14LiN
InChIKey:ZCSHNCUQKCANBX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:37.954
Molecular Formula:AlH4Li
InChIKey:OCZDCIYGECBNKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:337.782
Molecular Formula:C20H17ClNP
InChIKey:ARPLQAMUUDIHIT-UHFFFAOYSA-M
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Compound Information
Molecular Weight:172.1833
Molecular Formula:C10H8N2O
InChIKey:HGYKSFCCBATMSI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:129.2432
Molecular Formula:C8H19N
InChIKey:JGFZNNIVVJXRND-UHFFFAOYSA-N
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Compound Information
Molecular Weight:37.833
Molecular Formula:BH4Na
InChIKey:YOQDYZUWIQVZSF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:32.0419
Molecular Formula:CH4O
InChIKey:OKKJLVBELUTLKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:217.2206
Molecular Formula:C12H11NO3
InChIKey:LYWOFWNKZLWLPZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.2542
Molecular Formula:C12H15N
InChIKey:PSGFPTUMYLIVDX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:85.941
Molecular Formula:C4H11BO
InChIKey:RMCYTHFAWCWRFA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:363.4113
Molecular Formula:C24H17N3O
InChIKey:BSOAGODEMKWJIG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:656.188
Molecular Formula:C3BiF9O9S3
InChIKey:NYENCOMLZDQKNH-UHFFFAOYSA-K
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Compound Information
Molecular Weight:41.0519
Molecular Formula:C2H3N
InChIKey:WEVYAHXRMPXWCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:121.93
Molecular Formula:C6H7BO2
InChIKey:HXITXNWTGFUOAU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:225.2426
Molecular Formula:C14H11NO2
InChIKey:CYPJCGXWLXXEHL-AWEZNQCLSA-N
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Compound Information
Molecular Weight:225.2426
Molecular Formula:C14H11NO2
InChIKey:CYPJCGXWLXXEHL-CQSZACIVSA-N
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Compound Information
Molecular Weight:388.93
Molecular Formula:C8H16Cl2Rh2
InChIKey:OOQJCPOXJFCGCR-UHFFFAOYSA-L
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Compound Information
Molecular Weight:426.508
Molecular Formula:C24H27O3PS
InChIKey:QFDIHKFYKTXZAO-LJAQVGFWSA-N
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Compound Information
Molecular Weight:58.0791
Molecular Formula:C3H6O
InChIKey:CSCPPACGZOOCGX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:205.2099
Molecular Formula:C11H11NO3
InChIKey:CBMTTXBZZZABGG-LLVKDONJSA-N
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Compound Information
Molecular Weight:205.2099
Molecular Formula:C11H11NO3
InChIKey:CBMTTXBZZZABGG-NSHDSACASA-N
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Compound Information
Molecular Weight:117.1894
Molecular Formula:C6H15NO
InChIKey:Not Available
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Compound Information
Molecular Weight:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.2609
Molecular Formula:C6H14Si
InChIKey:HYWCXWRMUZYRPH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:189.2105
Molecular Formula:C11H11NO2
InChIKey:DFYBEJXLQXRVCP-LLVKDONJSA-N
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Compound Information
Molecular Weight:189.2105
Molecular Formula:C11H11NO2
InChIKey:DFYBEJXLQXRVCP-NSHDSACASA-N
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Compound Information
Molecular Weight:885.601
Molecular Formula:C28H19F9N3O11S3Sc
InChIKey:KJEKGDZPNKEGLR-UNLZZCTJSA-K
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Compound Information
Molecular Weight:258.74
Molecular Formula:F6NaSb
InChIKey:HKLMYZVMEYYVBS-UHFFFAOYSA-H
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Compound Information
Molecular Weight:108.642
Molecular Formula:C3H9ClSi
InChIKey:IJOOHPMOJXWVHK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:66.0614
Molecular Formula:C3H2N2
InChIKey:Not Available
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:YRKCREAYFQTBPV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:295.2927
Molecular Formula:C16H13N3O3
InChIKey:CXAUWNQUZMMPGF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:310.3902
Molecular Formula:C19H22N2O2
InChIKey:VJFMSYZSFUWQPZ-BIPCEHGGSA-N
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Compound Information
Molecular Weight:98.959
Molecular Formula:C2H4Cl2
InChIKey:WSLDOOZREJYCGB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.2497
Molecular Formula:C13H14O
InChIKey:FETDVTPMFRPTLM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:333.3805
Molecular Formula:C21H19NO3
InChIKey:CNOGDKSXBHNAIY-HZBHDWBUSA-N
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Compound Information
Molecular Weight:333.3805
Molecular Formula:C21H19NO3
InChIKey:CNOGDKSXBHNAIY-RBNQXFGJSA-N
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Compound Information
Molecular Weight:141.939
Molecular Formula:CH3I
InChIKey:INQOMBQAUSQDDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:161.1574
Molecular Formula:C9H7NO2
InChIKey:VCYBVWFTGAZHGH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:23.99771
Molecular Formula:HNa
InChIKey:MPMYQQHEHYDOCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:94.939
Molecular Formula:CH3Br
InChIKey:Not Available
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Compound Information
Molecular Weight:50.488
Molecular Formula:CH3Cl
InChIKey:NEHMKBQYUWJMIP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:Not Available
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Compound Information
Molecular Weight:189.1675
Molecular Formula:C10H7NO3
InChIKey:LPGDEHBASRKTDG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:79.0999
Molecular Formula:C5H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:112.557
Molecular Formula:C6H5Cl
InChIKey:MVPPADPHJFYWMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:223.2268
Molecular Formula:C14H9NO2
InChIKey:UWCPWBIMRYXUOU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:135.956
Molecular Formula:C7H9BO2
InChIKey:BIWQNIMLAISTBV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:237.2533
Molecular Formula:C15H11NO2
InChIKey:MFXRACFNCGDEFP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:181.634
Molecular Formula:C4H6CuO4
InChIKey:OPQARKPSCNTWTJ-UHFFFAOYSA-L
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Compound Information
Molecular Weight:440.2921
Molecular Formula:C18H15Bi
InChIKey:ZHXAZZQXWJJBHA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.0084
Molecular Formula:C6H5I
InChIKey:SNHMUERNLJLMHN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:325.8091
Molecular Formula:La2O3
InChIKey:MRELNEQAGSRDBK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:88.1515
Molecular Formula:C4H12N2
InChIKey:Not Available
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Compound Information
Molecular Weight:56.1056
Molecular Formula:HKO
InChIKey:KWYUFKZDYYNOTN-UHFFFAOYSA-M
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Compound Information
Molecular Weight:78.133
Molecular Formula:C2H6OS
InChIKey:IAZDPXIOMUYVGZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:181.576
Molecular Formula:C8H4ClNO2
InChIKey:XHDJYQWGFIBCEP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:219.946
Molecular Formula:C3Cl2N3NaO3
InChIKey:MSFGZHUJTJBYFA-UHFFFAOYSA-M
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Compound Information
Molecular Weight:216.021
Molecular Formula:C8H3Cl2NO2
InChIKey:AYGGQJHJRFZDFH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.409
Molecular Formula:C3Cl3N3O3
InChIKey:YRIZYWQGELRKNT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.1454
Molecular Formula:C8H6N2O2
InChIKey:SDQJTWBNWQABLE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:115.2092
Molecular Formula:C3H9N3Si
InChIKey:SEDZOYHHAIAQIW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.204
Molecular Formula:Cl3Fe
InChIKey:RBTARNINKXHZNM-UHFFFAOYSA-K
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Compound Information
Molecular Weight:163.1302
Molecular Formula:C8H5NO3
InChIKey:TXJUTRJFNRYTHH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:94.0699
Molecular Formula:CH6N2O3
InChIKey:AQLJVWUFPCUVLO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:60.052
Molecular Formula:C2H4O2
InChIKey:QTBSBXVTEAMEQO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:163.1302
Molecular Formula:C8H5NO3
InChIKey:MNDKNFRJYMSGTH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:270.322
Molecular Formula:K2O8S2
InChIKey:Not Available
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