1H-Benz[f]indene-1,3(2H)-dione

Base Information

• Chemical Name: 1H-Benz[f]indene-1,3(2H)-dione
• CAS No.: 22734-61-8
• Molecular Formula: C13H8O2
• Molecular Weight: 196.205
• Mol file: 22734-61-8.mol

Synonyms:Benz--indan-1,3-dion;indan-1,3-dione;indane-1,3-dione;

Chemical Property of 1H-Benz[f]indene-1,3(2H)-dione

Chemical Property:

• PSA: 34.14000
• LogP: 2.60890

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Benz[f]indene-1,3(2H)-dione

There total 8 articles about 1H-Benz[f]indene-1,3(2H)-dione 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: 91.0%

naphthalene-2,3-dicarboxylic acid diethyl ester (50919-54-5) → 1H-cyclopenta[b]naphthalene-1,3(2H)-dione (22734-61-8)

Guidance literature:

With sodium hydride; In ethyl acetate; at 105 ℃; for 5h;

DOI:10.1016/j.dyepig.2020.108182

Reference yield: 91.0%

naphthalene-2,3-dicarboxylic acid diethyl ester (50919-54-5) + ethyl acetate (141-78-6) → 1H-cyclopenta[b]naphthalene-1,3(2H)-dione (22734-61-8)

Guidance literature:

With sodium hydride; In mineral oil; at 105 ℃; for 5h;

DOI:10.1002/hlca.201900229

Reference yield: 63.0%

2,3-Naphthalenedicarboxylic anhydride (716-39-2) + ethyl acetoacetate (141-97-9) → 1H-cyclopenta[b]naphthalene-1,3(2H)-dione (22734-61-8)

Guidance literature:

2,3-Naphthalenedicarboxylic anhydride; ethyl acetoacetate; With triethylamine; In acetic anhydride; at 20 ℃; Inert atmosphere;

With hydrogenchloride; In acetic anhydride; Reflux;

DOI:10.1021/acs.joc.0c00567

upstream raw materials:

dimethyl 2,3-naphthalenedicarboxylate

ethyl acetate

naphthalene-2,3-dicarboxylic acid

2,3-Naphthalenedicarboxylic anhydride

Downstream raw materials:

1,3-dihydroxy-1,3-diphenylbenzindan-2-one 2-oxime

C₁₈H₁₁NO₂

(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)propanedinitrile

Refernces

• 1、 Pigot, Corentin,Noirbent, Guillaume,Peralta, Sébastien,Duval, Sylvain,Bui, Thanh-Tuan,Aubert, Pierre-Henri,Nechab, Malek,Gigmes, Didier,Dumur, Frédéric. "New push-pull dyes based on 2-(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)malononitrile: An amine-directed synthesis". . . Retrieved 2020/01/21.
• 2、 Pigot, Corentin,Noirbent, Guillaume,Peralta, Sébastien,Duval, Sylvain,Nechab, Malek,Gigmes, Didier,Dumur, Frédéric. "Unprecedented Nucleophilic Attack of Piperidine on the Electron Acceptor during the Synthesis of Push-Pull Dyes by a Knoevenagel Reaction". . . Retrieved 2019/11/29.