Isatin

Base Information

• Chemical Name: Isatin
• CAS No.: 91-56-5
• Deprecated CAS: 5815-00-9,84788-92-1,84788-92-1
• Molecular Formula: C8H5NO2
• Molecular Weight: 147.133
• Hs Code.: 2933.79
• European Community (EC) Number: 202-077-8
• NSC Number: 9262
• UNII: 82X95S7M06
• DSSTox Substance ID: DTXSID3038694
• Nikkaji Number: J4.342G,J608.794I
• Wikipedia: Isatin
• Wikidata: Q421348
• Pharos Ligand ID: 837625PAHCTN
• Metabolomics Workbench ID: 51362
• ChEMBL ID: CHEMBL326294
• Mol file: 91-56-5.mol

Synonyms:Indole-2,3-dione(8CI);2,3-Dihydro-1H-indole-2,3-dione;2,3-Dihydroindole-2,3-dione;2,3-Diketoindoline;2,3-Dioxo-2,3-dihydroindole;2,3-Dioxoindoline;2,3-Indolindione;2,3-Indolinedione;Isatic acid lactam;Isatin;Isatine;Isatinic acid anhydride;NSC 9262;Pseudoisatin;o-Aminobenzoylformic anhydride;

Chemical Property of Isatin

Chemical Property:

• Appearance/Colour: yellow to reddish crystalline solid
• Vapor Pressure: 0Pa at 25℃
• Melting Point: 193-195 °C (dec.)(lit.)
• Refractive Index: 1.661
• Boiling Point: 360.3 °C at 760 mmHg
• PKA: 10.34±0.20(Predicted)
• Flash Point: 171.7 °C
• PSA: 46.17000
• Density: 1.367 g/cm³
• LogP: 0.95940
• Storage Temp.: Store at RT.
• Solubility.: soluble
• Water Solubility.: Soluble in water (1.9 g/L at 20°C).
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 147.032028402
• Heavy Atom Count: 11
• Complexity: 212

Purity/Quality:

98% ^*data from raw suppliers

Isatin 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Indoles
• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C(=O)N2
• Uses: (1) The product is used as medicine and dye intermediates ,and it is used for the production of drug? quinophan, dye disperse Yellow E-3G ; in chemical analysis,it is used as reagents for the determination of copper ions, mercaptans, thiophene,? indoxyl-beta-glucoside. (2) Isatin as a reference material for the preparation of indigo and Maya blue; for the preparation of phthalazinone derivatives, spirooxindole derivatives, the expression of P-glycoprotein for multi-drug resistant cells; The ketone is fused to form indole-2-one as a tubercular mycobacterial protein tyrosine phosphatase B, a potent selective inhibitor, as a powerful antimicrobial and antifungal triazole-isatine complex, And the Knoevenagel enrichment reaction; the isatin is activated by the direct sp2/sp3C-H bond, and undergoes a reaction with the cyclopentadienyl-Pd (II) catalyzes the CH addition reaction to form 3-substituted-3-hydroxy 2-oxindole. manufacture of vat dyes. In analytical chemistry as a reagent for cuprous ions, mercaptans, thiophene, and indican. Isatin is an endogenous monoamine oxidize (MAO) inhibitor involved in stress and anxiety. Additionally, isatin inhibits alkaline phosphatase (ALP), nitric oxide (NO)-stimulated soluble guanylate cyclase, and other enzymes. Isatins undergo a one-pot Wolff-Kishner like reduction with hydrazine hydrate, under surprisingly mild conditions, to give the corresponding oxindoles. It is used as chromatographic spray reagent for amino acid detection. Isatin can be used as a reactant to prepare:Phthalazinone derivatives.Spirooxindole derivatives.Agents against multidrug-resistant cells expressing P-glycoprotein.Thiazolidinones spiro-fused to indolin-2-ones as potent and selective inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B.Triazole-isatine compounds as potential antibacterial and antifungal agents.Biologically relevant scaffolds such as spiro[indole-thiazolidinones].It can be a reactant for:Cascade reactions with heterocyclic ketene aminals.Knoevenagel condensation reactions.Isatin can also be used as a chromatographic spray reagent for amino acids, and also as a reference material in the preparation of indigo and Maya Blue. It is responsible for the yellow color exhibited by the "Maya Yellow" pigment.
• production method: Condensation of chloral and aniline? can generate? oximide-acetanilide, and then by cyclization, hydrolysis , isatin is obtained.

Technology Process of Isatin

There total 293 articles about Isatin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

3-benzyl-3-(tert-butylperoxy)-indolin-2-one → indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) + benzaldehyde (100-52-7)

Guidance literature:

With iron(III) chloride hexahydrate; In acetonitrile; at 100 ℃; Sealed tube;

DOI:10.1021/acs.orglett.9b00155

Reference yield: 64.0%

indole (120-72-9) → 2-oxoindole (59-48-3) + indirubin (479-41-4) + indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1)

Guidance literature:

With chloro(meso-tetrakis(2,6-dichlorophenyl)porphyrinato)manganese(III); dihydrogen peroxide; In acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1016/j.apcata.2013.11.023

Reference yield: 50.0%

indole (120-72-9) → 2-oxoindole (59-48-3) + indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) + 2,2-di(3-indolyl)-3-indolone (17646-95-6)

Guidance literature:

With chloro(meso-tetrakis(2,6-dichlorophenyl)porphyrinato)manganese(III); chloro[2-nitro-5,10,15,20-tetrakis(2,6-diclorophenyl)porphyrinate]manganese(III); In acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1016/j.apcata.2013.11.023

upstream raw materials:

dioxindol

3-hydroxy-1H-indole-2-carboxylic acid

3-amino-quinoline-2,4-diol

3-indoxyl acetate

Downstream raw materials:

3-<5-<5-(1,2-Dihydro-2-oxo-3H-indol-3-yliden)-1,5-dihydro-2H-thiophen-2-yliden>-1,5-dihydro-2H-thiophen-2-yliden>-1,3-dihydro-2H-indol-2-on

2-(pyridin-4-yl)quinoline-4-carboxylic acid

2-(5-p-tolyl-[2]thienyl)-quinoline-4-carboxylic acid

5,6-dihydro-4H,8H-benzo[b]quino[1,8-gh][1,6]naphthyridine-9-carboxylic acid

Refernces

• 1、 Singh, Anju,Kalamuddin, Md,Maqbool, Mudasir,Mohmmed, Asif,Malhotra, Pawan,Hoda, Nasimul. "Quinoline carboxamide core moiety-based compounds inhibit P. falciparum falcipain-2: Design, synthesis and antimalarial efficacy studies". . . Retrieved 2020/12/07.
• 2、 Wang, Yin-Feng,Yi, Xiu-Guang,Fang, Xiao-Niu,Guo, Jin,Lai, Fei-Ping,Xie, Shi-Kun. "Hydrothermal Preparation, Crystal Structure, Photophysical Properties and Theoretical Calculation of a Cu(II) Complex". . p. 169 - 174. Retrieved 2020/05/29.