3484-32-0

Basic information

• Product Name: 1-METHYL-5-NITRO-ISATIN
• Synonyms: 1-METHYL-5-NITRO-ISATIN;1-METHYL-5-NITROINDOLINE-2,3-DIONE
• CAS NO: 3484-32-0
• Molecular Formula: C₉H₆N₂O₄
• Molecular Weight: 206.15
• Product Categories: pharmacetical
• Mol File: 3484-32-0.mol
• Article Data: 47

Chemical Properties

• Boiling Point: 391.9°C at 760 mmHg
• Flash Point: 190.8°C
• Appearance: /
• Density: 1.533g/cm³
• Vapor Pressure: 2.38E-06mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-METHYL-5-NITRO-ISATIN(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-5-NITRO-ISATIN(3484-32-0)
• EPA Substance Registry System: 1-METHYL-5-NITRO-ISATIN(3484-32-0)

Safety Data

• Hazardous Substances Data: 3484-32-0(Hazardous Substances Data)

Usage

Preparation

A mixture of nitroisatin 31 (10 g, 0.052 mol), MeI (16.21 ml, 0.260 ?mol) and K2CO3 (21.56 g, 1.56 mol) in anhydrous DMF was stirred ?overnight at room temperature. Water was added to the reaction ?mixture and acidified with dilute HCl till acidic to pH paper. A ?yellow solid separated, 1-Methyl-5-nitroisatin was filtered and washed thoroughly ?with water till neutral to pH paper and air dried to a constant weight (9.66 g).

Synthesis Reference(s)

Journal of Medicinal Chemistry, 39, p. 5072, 1996 DOI: 10.1021/jm960603e

InChI:InChI=1/C9H6N2O4/c1-10-7-3-2-5(11(14)15)4-6(7)8(12)9(10)13/h2-4H,1H3

Upstream product

• 2058-74-4 1-methyl-1H-indole-2,3-dione 
• 611-09-6 5-nitroisatin 
• 74-88-4 methyl iodide 
• 5279-61-8 N-methyl-4-(4-nitrophenyl)formamide 
• 29906-67-0 1-methyl-5-nitro-1H-indole 
• 91-56-5 indole-2,3-dione 
• 20870-89-7 1-methyl-5-nitro-1,3-dihydro-indol-2-one 
• 74-87-3 methylene chloride 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1219433-01-8 10'-amino-1,2-dihydro-1-methyl-5-nitro-2,7'-dioxospiro[3H-indole-3,8'(7H,8H)-phenaleno[1,2-b]pyran]-9'-carbonitrile 
• 1379768-26-9 C₂₇H₃₁N₃O₉ 
• 1394843-51-6 3-hydroxy-1-methyl-6-nitroquinolin-2(1H)-one 
• 2216750-84-2 2-((6-amino-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)oxy)-N-methylacetamide 

Relevant articles and documents

Activation of the NC-H bond of Baylis-Hillman adducts of N-methylisatin with CAN/ROH

A facile method for activation of the NC-H bond of N-methylisatin and Baylis-Hillman adducts of N-methylisatin with cerium ammonium nitrate (CAN) and saturated and unsaturated alcohols is reported. Adducts bearing an ester group at the activated alkene afford functionalized ethers, while those with a nitrile afforded ethers and nitrated aromatic products in good yield.

Synthesis of new spiroindolinones incorporating a benzothiazole moiety as antioxidant agents

3H-Spiro[1,3-benzothiazole-2,3′-indol]-2′(1′H)-ones 3a-c and 4a-e were synthesized from treating the 5-substituted 1H-indole-2,3-diones with 2-aminothiophenol in ethanol. The structures were confirmed by elemental analyses, spectrometry (IR, 1H NMR, 13C NMR, HSQC-2D and LCMS-APCI) and single crystal X-ray analysis. The new compounds were screened for their antioxidant activities such as the Fe3+/ascorbate system induced inhibition of lipid peroxidation (LP) in liposomes, trolox equivalent antioxidant capacity (TEAC), scavenging effect on diphenylpicryl hydrazine (DPPH{radical dot}), and reducing power. These compounds showed potent scavenging activities against DPPH{radical dot} and 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS{radical dot}+) radicals, reducing powers, and strong inhibitory capacity on lipid peroxidation. Compound 4a incorporating methyl both at R1 and R2 was found to be the most potent antioxidant described in this study. Compounds 3b and 4b were selected as representative compounds by the National Cancer Institute for screening against anticancer activity and these compounds were found to be cytotoxic against CNS cancer cell line SNB-75 in the primary screen.

Synthesis, characterization and anticancer activity of (5,1-substituted)-3-(indoline-4-(thiophene- 2-yl-methylene)-2-(p-tolyl)-2-methylene)-4,3-dihydro-1h-imidazole-5-one derivatives

The synthesis of novel imidazole-5-one derivatives (5a-j) was allowed in a conventional method by way of Erlenmeyer and Schiff base mechanism. Compound 2a was synthesized by Erlenmeyer reaction of N-(4-methoxy benzoyl)glycine with 2-thiophene-carboxaldehyde in the presence of acetic anhydride and anhydrous sodium acetate. Finally, it undergoes dehydration reaction with Schiff bases of isatin derivatives (4a-j) to yield final compounds 5a-j. The organic potentials of the newly synthesized imidazole-5-one derivatives have been evaluated for their in vitro anticancer activity by MTT assay method. It against MCF-7 cells as comparison with doxorubicin popular drug. The synthesized compounds 5e, 5f and 5j exhibited excellent anticancer activity against MCF-7 cell lines.

Novel isatin derivative nitration method

The invention belongs to the technical field of chemical pharmacy and fine chemical engineering preparation, and particularly discloses a novel isatin derivative nitration method. Trifluoroacetic acidis adopted to replace traditional sulfuric acid, so tha