21905-78-2

Basic information

• Product Name: N-ACETYLOXINDOLE 97
• Synonyms: N-ACETYLOXINDOLE 97;N-Acetyl-2-oxindole;1-Acetyl-1H-indole-2(3H)-one;1-Acetyl-2-indolinone;1-Acetyloxindole;2H-Indol-2-one, 1-acetyl-1,3-dihydro-;2-Indolinone, 1-acetyl-;Nsc286428
• CAS NO: 21905-78-2
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• EINECS: 1533716-785-6
• Mol File: 21905-78-2.mol
• Article Data: 19

Chemical Properties

• Melting Point: 127-131 °C(lit.)
• Boiling Point: 399.8°Cat760mmHg
• Flash Point: 203.5°C
• Appearance: /
• Density: 1.275g/cm³
• Vapor Pressure: 1.33E-06mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: 2-8°C
• PKA: -0.58±0.20(Predicted)
• CAS DataBase Reference: N-ACETYLOXINDOLE 97(CAS DataBase Reference)
• NIST Chemistry Reference: N-ACETYLOXINDOLE 97(21905-78-2)
• EPA Substance Registry System: N-ACETYLOXINDOLE 97(21905-78-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 21905-78-2(Hazardous Substances Data)

Usage

Description

N-ACETYLOXINDOLE 97, also known as Acetyloxindole, is a chemical compound with the molecular formula C10H9NO2. It is a derivative of indole, a heterocyclic aromatic organic compound that contains a benzene ring fused to a pyrrole ring. N-ACETYLOXINDOLE 97 has potential applications in various fields due to its unique chemical properties and structure.

Uses

Used in Pharmaceutical Industry:
N-ACETYLOXINDOLE 97 is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a valuable building block for the development of new drugs with specific therapeutic properties.
Used in Antithrombotic Applications:
N-ACETYLOXINDOLE 97 is used as a potent and bioavailable selective P2Y1 antagonist in the area of antithrombotics. It plays a crucial role in the development of drugs that help prevent blood clot formation, which is essential in treating conditions such as stroke, heart attack, and deep vein thrombosis.
Used in Antibacterial Applications:
N-ACETYLOXINDOLE 97 is used as a potential inhibitor of salicylate synthase in Mycobacterium tuberculosis. By targeting this enzyme, it can help in the development of new antibiotics to combat drug-resistant strains of tuberculosis, a significant global health concern.

InChI:InChI=1/C10H9NO2/c1-7(12)11-9-5-3-2-4-8(9)6-10(11)13/h2-5H,6H2,1H3

Upstream product

• 59-48-3 2-oxoindole 
• 108-24-7 acetic anhydride 
• 62-53-3 aniline 
• 7270-63-5 5-diazo-2,2-dimethyl-1,3-dioxane-4,6-dion 
• 103-84-4 Acetanilid 
• 574-17-4 1-acetyl-1H-indole-2,3-dione 
• 3342-78-7 2-(2-aminophenyl)acetic acid 
• 576-15-8 N-acetylindole 
• 937-14-4 3-chloro-benzenecarboperoxoic acid 
• 103205-34-1 2-(2-acetamidophenyl)acetic acid 

Downstream Products

• 142634-90-0 1-Acetylspiro-2'(1')-one 
• 182753-51-1 1-Acetyl-3-[1-[2-(3-methyl-but-2-enyloxy)-phenyl]-meth-(E)-ylidene]-1,3-dihydro-indol-2-one 
• 19155-24-9 3,3-dimethyloxindole 
• 72934-84-0 1-acetyl-3,3-dimethylindolin-2-one 
• 59-48-3 2-oxoindole 
• 476-34-6 isoindigo 
• 114985-63-6 1-acetyl-5-nitroindol-2-one 
• 159212-34-7 3-(phenethylamino-methylene)-indolin-2-one 
• 141210-72-2 3-[(phenylamino)methylene]indolin-2-one 
• 14192-31-5 3,3-dibenzyl-1,3-dihydroindol-2-one 
• 114727-67-2 [3,3-Bis-(3,4-dichloro-benzyl)-2-oxo-2,3-dihydro-indol-1-yl]-acetic acid benzyl ester 
• 114727-66-1 C₂₅H₂₀ClNO₃ 
• 114727-65-0 C₂₅H₂₁NO₃ 

Relevant articles and documents

Synthesis of 4-azachromeno[2,3-b]indol-11(6H)-one and its derivatives as analogues of ellipticine

4-Azachromeno[2,3-b]indol-11(6H)-ones (4) and their derivatives (5) as analogues of ellipticine were synthesized through a straightforward, two or three-step process. Tetracyclic heterocycles (4) were obtained by facile cyclization of indolin-2-ones (2) or (3) and 2-chloronicotinoyl chloride under the condition of the 'Jensen'-reaction. Alkylation of the compounds (4) afforded 6-substituted 4-azachromeno[2,3-b]indol-ll(6H)-ones.

Synthesis of oxindole from acetanilide via Ir(iii)-catalyzed C-H carbenoid functionalization

Herein we disclose the first report on the synthesis of oxindole derivatives from acetanilide via Ir(iii)-catalyzed intermolecular C-H functionalization with diazotized Meldrum's acid. A broad range of substituted anilides were found to react smoothly under the Ir(iii)-catalytic system to afford the corresponding N-protected oxindoles. The N-protecting groups, such as Ac, Bz or Piv, can be easily removed to furnish the oxindole. Various synthetic applications of the synthesized oxindole were also demonstrated.

General synthesis of mono-, di-, and tri-acetylated indoles from indolin-2-ones

Having developed the one-pot triacetylation of indolin-3-ones, we have now devised a simple two-step reaction sequences to produce di- and mono-acetylated indoles from indolin-2-ones. The indolin-2-ones were first subjected to acetylation in the presence of acetic anhydride and a catalytic amount of N,N-dimethylaminopyridine to give 2-acetoxy-1,3-diacetylindoles. Subsequently, an enzyme-assisted deacetylation resulted in the chemoselective deprotection of the acetoxy group to produce 1,3-diacetyl-2-hydroxyindoles. However, a chemical deacetylation of 2-acetoxy-1,3-diacetylinoles under mild basic or acidic conditions resulted in the formation of 3-acetyl-2-hydroxyindoles.