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183075

Sigma-Aldrich

1-Methylisatin

97%

Synonym(s):

N-Methylindoline-2,3-dione, NSC 42449

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About This Item

Empirical Formula (Hill Notation):
C9H7NO2
CAS Number:
2058-74-4
Molecular Weight:
161.16
EC Number:
218-164-9
MDL number:
MFCD00005812
UNSPSC Code:
12352100
PubChem Substance ID:
24851030
NACRES:
NA.22

Assay

97%

form

solid

mp

130-133 °C (lit.)

SMILES string

CN1C(=O)C(=O)c2ccccc12

InChI

1S/C9H7NO2/c1-10-7-5-3-2-4-6(7)8(11)9(10)12/h2-5H,1H3

InChI key

VCYBVWFTGAZHGH-UHFFFAOYSA-N

Gene Information

human ... CASP3(836)

Related Categories

General description

The interaction between 1-methylisatin and human adult haemoglobin was studied using the circular dichroism (CD) spectroscopic, anisotropy and FTIR investigations.

Application

  • Reactant for stereoselective preparation of spirobicyclic and bis-spirotricyclic pyrazolidinones
  • Reactant for regioselective preparation of spirocyclic oxindole-butenolides
  • Reactant for synthesis of spiro-oxindoles
  • Reactant for preparation of unsymmetrical oxindoles
  • Reactant for stereoselective preparation of hydroxyloxindoles via Morita-Baylis-Hillman reaction
  • Reactant for preparation of pyridinecarboxylic acid [(oxo)indolylidene)hydrazide derivatives (Schiff base hydrazides) as antibacterial agents

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301,H315,H318,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Verena Schulz et al.
Organic letters, 9(9), 1745-1748 (2007-03-31)
[reaction: see text] The in situ preparation of a sulfonium ylide reagent achieved the highly diastereoselective epoxidation of isatins, so that a new and straightforward access to biologically significant spiro-epoxyoxindoles is provided. The first investigations of an asymmetric version are
María C Rodríguez-Argüelles et al.
Journal of inorganic biochemistry, 101(1), 138-147 (2006-10-31)
Cobalt(II), nickel(II), copper(II) and zinc(II) complexes of 2-thiophenecarbonyl and isonicotinoyl hydrazones of 3-(N-methyl)isatin (HL(1) and HL(2), respectively) were synthesized and characterized, being the crystal structures of HL(1), HL(2) and [Ni(L(1))(2)].2CHCl(3) elucidated by X-ray diffraction techniques. The in vitro antimicrobial activity
M S Mirrlees et al.
Drug design and discovery, 11(3), 223-230 (1994-04-01)
Alkaline hydrolysis of the title isatin 4 in unbuffered solution obeys a rate law such that kobs varies; is directly proportional to [OH-]2 at pH 10 changes smoothly to kobs varies; is directly proportional to [OG-] by pH 13. As
L Sebastian et al.
Letters in applied microbiology, 55(3), 234-239 (2012-06-29)
To investigate the drug to drug interaction of N-methylisatin-β-thiosemicarbazone (MIBT) derivative (SCH16) with ribavirin, mycophenolic acid and pentoxifylline against Japanese encephalitis virus in vitro. Our earlier studies have reported significant antiviral activity of these compounds against Japanese encephalitis virus in
Jaime F Martínez Suárez et al.
The Journal of organic chemistry, 84(11), 6879-6885 (2019-05-16)
Isatin in a solution of dry N,N-dimethylformamide/NaClO4 is electroreduced in the presence of CH3I. N-methylisatin (NMI) is obtained in quantitative molar yield and high current efficiency by controlled potential electrolysis (CPE). NMI and N-methylisatoic anhydride are the reaction products when
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