4269-16-3

Basic information

• Product Name: 4-methoxyfluoren-9-one
• Synonyms: 4-methoxyfluoren-9-one
• CAS NO: 4269-16-3
• Molecular Formula: C₁₄H₁₀O₂
• Molecular Weight: 210.228
• Mol File: 4269-16-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 114.5-115.5 °C(Solv: methanol (67-56-1))
• Boiling Point: 383.6 °C at 760 mmHg
• Flash Point: 186.3 °C
• Appearance: /
• Density: 1.245 g/cm³
• Vapor Pressure: 4.34E-06mmHg at 25°C
• Refractive Index: 1.637
• CAS DataBase Reference: 4-methoxyfluoren-9-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methoxyfluoren-9-one(4269-16-3)
• EPA Substance Registry System: 4-methoxyfluoren-9-one(4269-16-3)

Safety Data

• Hazardous Substances Data: 4269-16-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H10O2/c1-16-12-8-4-7-11-13(12)9-5-2-3-6-10(9)14(11)15/h2-8H,1H3

Upstream product

• 890098-06-3 (2-bromophenyl)(3-methoxyphenyl)methanone 
• 292151-99-6 (2'-methoxybiphenyl-2-yl)methanamine 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 2042-37-7 o-cyanobromobenzene 
• 1527-89-5 3-methoxybenzonitrile 
• 108-90-7 chlorobenzene 
• 2005-10-9 6H-benzo[c]chromen-6-one 
• 207558-46-1 6-methoxy-2-(N,N-diethylcarboxamido)phenylboronic acid 
• 120270-44-2 N,N-diethyl-6-methoxy-2′-methylbiphenyl-2-carboxamide 
• 120270-53-3 4-methoxy-10-phenanthrol 
• 62924-93-0 N,N-diethyl-3-methoxybenzamide 
• 615-37-2 ortho-methylphenyl iodide 
• 4269-15-2 4-aminofluorenone 
• 1986-00-1 4-hydroxy-9-fluorenone 

Downstream Products

• 416857-80-2 2,2-diphenyl-2H-pyrano[5,6-c]fluorenone 
• 387392-70-3 2-(3,4-dimethoxy-phenyl)-2-isopropyl-5-(4-methoxy-9H-fluoren-9-ylamino)-pentanenitrile 
• 1986-00-1 4-hydroxy-9-fluorenone 

Relevant articles and documents

Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

Highly substituted fluorenones are readily prepared in mostly fair to good yields via metal- and additive-free TBHP-promoted cross-dehydrogenative coupling (CDC) of readily accessible N-methyl-2-(aminomethyl)biphenyls and 2-(aminomethyl)biphenyls. This methodology is compatible with numerous functional groups (methoxy, cyano, nitro, chloro, and SEM and TBS-protective groups for phenols) and was further utilized in the first total synthesis of the natural product nobilone.

General method for functionalized polyaryl synthesis via aryne intermediates

A method for base-promoted arylation of arenes and heterocycles by aryl halides and aryl triflates is described. Additionally, in situ electrophilic trapping of ArLi intermediates generated in the reaction of benzyne with deprotonated arenes or heterocycles has been developed, providing rapid and easy access to a wide range of highly functionalized polyaryls. Base-promoted arylation methodology complements transition-metal-catalyzed direct arylation and allows access to structures that are not easily accessible via other direct arylation methods. The reactions are highly functional-group tolerant, with alkene, ether, dimethylamino, trifluoromethyl, ester, cyano, halide, hydroxyl, and silyl functionalities compatible with reaction conditions.

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.