17666-95-4

Basic information

• Product Name: 5-methoxy-1H-indene-1,3(2H)-dione
• CAS NO: 17666-95-4
• Molecular Formula: C₁₀H₈O₃
• Molecular Weight: 176.1687
• Mol File: 17666-95-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 355.2°C at 760 mmHg
• Flash Point: 161.5°C
• Density: 1.299g/cm³
• Vapor Pressure: 3.19E-05mmHg at 25°C
• Refractive Index: 1.584
• CAS DataBase Reference: 5-methoxy-1H-indene-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methoxy-1H-indene-1,3(2H)-dione(17666-95-4)
• EPA Substance Registry System: 5-methoxy-1H-indene-1,3(2H)-dione(17666-95-4)

Safety Data

• Hazardous Substances Data: 17666-95-4(Hazardous Substances Data)

Upstream product

• 7507-86-0 2-bromo-5-methoxy-benzaldehyde 
• 100-09-4 4-methoxybenzoic acid 
• 908128-22-3 7-methoxy-1,4-dioxo-3-(phenyliodonio)-1,4-dihydronaphthalen-2-olate 
• 148502-18-5 5-methoxy-1-oxoindan-3-ylammonium chloride 
• 100-07-2 4-methoxy-benzoyl chloride 
• 1663-67-8 malonoyl dichloride 
• 17666-97-6 5-Methoxy-1,3-dioxo-indan-2-carboxylic acid ethyl ester 

Downstream Products

• 507484-59-5 2-(6-methoxy-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile 
• 17828-67-0 5-methoxy-2-phenyl-1H-indene-1,3(2H)-dione 
• 106507-42-0 2,2-dihydroxy-5-methoxyindane-1,3-dione 

Relevant articles and documents

Sulfoximines Assisted Rh(III)-Catalyzed C-H Activation/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines

A facile access to highly fused tetracyclic indeno-1,2-benzothiazines has been established via a Rh(III)-catalyzed C-H bond activation and intramolecular annulation cascade between sulfoximides and all-carbon diazo indandiones. This strategy is characterized by the fact that the diazo coupling partners do not require preactivation, along with its high efficiency, broad substrate generality, and facile transformation. Particularly, the highly conjugated tetracyclic products demonstrate good optical properties and can easily enter cells to emit bright fluorescence for live cell imaging.

Synthetic methods for the preparation of ARQ 501 (β-Lapachone) human blood metabolites

ARQ 501 (3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b] pyran-5,6-dione), a synthetic version of β-Lapachone, is a promising anti-cancer agent currently in multiple Phase II clinical trials. Promising anti-cancer activity was observed in Phase I and Phase II trials. Metabolism by red blood cells of drugs is an understudied area of research and the metabolites arising from oxidative ring opening (M2 and M3), decarbonylation/ring contraction (M5), and decarbonylation/oxidation (M4 and M6) of ARQ 501 offer a unique opportunity to provide insight into these metabolic processes. Since these metabolites were not detected in in vitro incubations of ARQ 501 with liver microsomes and were structurally diverse, confirmation by chemical synthesis was considered essential. In this report, we disclose the synthetic routes employed and the characterization of the reference standards for these blood metabolites as well as additional postulated structures, which were not confirmed as metabolites.

Acylation of Aroyl Chlorides via a Template Friedel-Crafts Process: Synthesis of Indan-1,3-diones

Variously substituted indan-1,3-diones have been regioselectively prepared in a one-pot synthesis by sequential cross-condensation-cycloacylation of aromatic acyl chlorides and acetyl chloride or malonyl dichloride, electrophilic acylation of aromatic acyl chlorides representing the key step in the process.The synergism of the aromatic carbonyl enolization and the organization of the reacting system promoted by the metal is emphasized to account for the mild reaction conditions.