15144-82-8

Basic information

• Product Name: 9H-Fluoren-9-one, 3-methoxy-
• CAS NO: 15144-82-8
• Molecular Formula: C14H10O2
• Molecular Weight: 210.232
• Mol File: 15144-82-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 9H-Fluoren-9-one, 3-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 9H-Fluoren-9-one, 3-methoxy-(15144-82-8)
• EPA Substance Registry System: 9H-Fluoren-9-one, 3-methoxy-(15144-82-8)

Safety Data

• Hazardous Substances Data: 15144-82-8(Hazardous Substances Data)

Upstream product

• 59142-63-1 2-bromo-4'-methoxy-benzophenone 
• 59142-57-3 (2-bromo-4-methoxyphenyl)phenylmethanone 
• 174899-66-2 1-(n-butyl)-3-methylimidazolium triflate 
• 174899-83-3 1-butyl-3-methylimidazolium trifluoromethanesulfonimide 
• 66003-76-7 Diphenyliodonium triflate 
• 100-09-4 4-methoxybenzoic acid 

Downstream Products

• 105448-92-8 3-methoxy-10,10-diphenylphenanthren-9(10H)-one 
• 6344-67-8 3-hydroxyfluorene 
• 1253118-46-5 3-(benzyloxy)-9H-fluoren-9-one 
• 109866-04-8 (9-chloro-9-phenyl-fluoren-3-yl)-methyl ether 
• 416857-86-8 6-hydroxy-6-methyl-2,2-diphenyl-2H-pyrano[5,6-b]fluorene 
• 416857-79-9 2,2-diphenyl-2H-pyrano[5,6-b]fluorenone 

Relevant articles and documents

Ring-closure reaction of 2-benzoylbenzenediazonium salts in 1-butyl-3- methylimidazolium ionic liquids

A ring-closure reaction by thermal dediazoniation of 2-substituted benzenediazonium tetrafluoroborates in imidazolium-based ionic liquids was investigated. Dediazoniation of 2-(4-R-benzoyl)benzenediazonium tetrafluoroborates (R = H, Me, OMe, Cl) in ionic liquid [BMIM][TfO] gave 3-R-9-fluorenones as ring-closure products and 2-(4-R-benzoyl)phenyl trifluoromethanesulfonates as substitution products. Dediazoniation in [BMIM][Tf2N] afforded 3-R-9-fluorenones and R-C6H4-CO-C6H4-OSO(CF3)(NSO2CF3). Yields of the ring-closure products were higher in [BMIM][Tf2N] than in [BMIM][TfO]. 2-Benzylbenzenediazonium and 2-phenoxybenzenediazonium tetrafluoroborates exclusively produced substitution products in both ionic liquids. DFT calculations suggest that electron transfer from the anion to render homolytic process should be induced more readily in [BMIM][Tf2N] than in [BMIM][TfO]. This ability may be responsible for the higher yields of the ring-closure products via homolytic pathway and the smaller yields of the substitution products via heterolytic pathway in [BMIM][Tf2N].

Photoinduced C-Br homolysis of 2-bromobenzophenones and Pschorr ring closure of 2-aroylaryl radicals to fluorenones

(Chemical Equation Presented) A variety of diversely substituted 2-aroylaryl radicals, generated by photoinduced homolysis of 2-bromoarylketones, is shown to undergo Pschorr cyclization to yield fluorenones in moderate to excellent yields. The photochemical results illustrate that the substituents in the two phenyl rings of the 2-bromobenzophenone skeleton exert a dramatic influence on the reactivity of the derived 2-aroylaryl radicals. The disubstitution by methoxy groups in the radical ring renders the aryl σ-radical highly electrophilic and unreactive for hydrogen abstraction and cyclization. On the other hand, the substituents in the non-radical ring that strongly stabilize the hydrofluorenyl π-radical, formed subsequent to the attack of the 2-aroylaryl radical on the non-radical ring, promote cyclization to furnish fluorenones in excellent isolated yields.