9-Fluorenone

Base Information

• Chemical Name: 9-Fluorenone
• CAS No.: 486-25-9
• Molecular Formula: C13H8O
• Molecular Weight: 180.206
• Hs Code.: 29143900
• European Community (EC) Number: 207-630-7
• NSC Number: 5181
• UNII: AZ9T83S2AQ
• DSSTox Substance ID: DTXSID6049307
• Nikkaji Number: J2.596H
• Wikipedia: Fluorenone
• Wikidata: Q421328
• Metabolomics Workbench ID: 51092
• ChEMBL ID: CHEMBL571655
• Mol file: 486-25-9.mol

Synonyms:9-fluorenone;fluoren-9-one

Chemical Property of 9-Fluorenone

Chemical Property:

• Appearance/Colour: yellow flakes, chips or crystalline powder
• Vapor Pressure: 8.01E-05mmHg at 25°C
• Melting Point: 80-83 °C(lit.)
• Refractive Index: 1.667
• Boiling Point: 341.499 °C at 760 mmHg
• Flash Point: 144.142 °C
• PSA: 17.07000
• Density: 1.244 g/cm³
• LogP: 2.89800
• Storage Temp.: Store at RT.
• Water Solubility.: insoluble
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 180.057514874
• Heavy Atom Count: 14
• Complexity: 222

Purity/Quality:

99% ^*data from raw suppliers

9-Fluorenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C2C(=C1)C3=CC=CC=C3C2=O
• Description: 9-fluorenone is an important intermediate for organic synthesis. It can be used to manufacture a variety of fine chemicals, mainly used as a modifier for the production of polymer materials, bisphenol fluorene, fluorenyl benzoxazine resin, acrylic resin, polyester, polycarbonate and epoxy resin. In the laboratory, fluorene was used as the raw material, dimethyl sulfoxide as the solvent, sodium hydroxide as the catalyst and oxygen as the oxidant. The oxidizing reaction was carried out by a tower packing reactor. The reaction solution was cooled and filtered to obtain a crude fluorenone. The content of crude fluorenone is 93%. We can recover 94% of the solvent and part of the crude fluorenone through distillation of the filtrate. The crude fluorenone is purified by directional crystallization to obtain yellow flaky fluorenone that have a purity of 99.8% or more.
• Uses: 9-Fluorenone is used in the preparation of antimalarial drugs. It is a fluorene derivative. Further, it is used in functional polymer and in dyes. 9-Fluorenone has been extensively used as a precursor to synthesize a variety of organic electronic materials. Some of the general examples are:Synthesis of host for the blue and green phosphorescent organic light emitting diodes (PHOLEDs).Synthesis of fluorene-based molecular motors.Synthesis of open-shell Chichibabin′s hydrocarbons as potential organic spintronic materials.It also acts as a sensitizer in the formation of picene via photosensitization of 1,2-di(1-naphthyl)ethane.

Technology Process of 9-Fluorenone

There total 891 articles about 9-Fluorenone 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: 85.0%

9-Benzylidene-9H-fluorene (1836-87-9) → 9-fluorenone (486-25-9,952573-42-1) + benzaldehyde (100-52-7)

Guidance literature:

With Celite; pyridinium chlorochromate; In dichloromethane; for 28h; Heating; highly selective oxidative cleavage;

Reference yield: 58.0%

biphenyl (92-52-4,1594-86-1) + carbon monoxide (201230-82-2) → 9-fluorenone (486-25-9,952573-42-1) + biphenyl-4-carboxylic acid (92-92-2)

Guidance literature:

With manganese(IV) oxide; trifluoroacetic acid; trifluoroacetic anhydride; palladium diacetate; at 20 ℃; for 20h; under 750.06 Torr;

DOI:10.1023/A:1013970406482

Reference yield: 45.0%

9H-fluoren-9-yl bromide (1940-57-4) + C9H7N2O3(1-)*Ag(1+) (107985-36-4) → 9-fluorenone (486-25-9,952573-42-1) + (Z)-2,3-bis(4-methoxyphenyl)but-2-enedinitrle (4680-92-6) + 4-methoxybenzoic acid (100-09-4) + 9-fluorenyl(4-methoxyphenyl)(nitro)acetonitrile (107960-28-1)

Guidance literature:

In benzene; for 55h; Ambient temperature;

upstream raw materials:

tetrachloromethane

methyl 9-fluoreneglyoxylate

9,9'-bis-(2-nitro-phenylsulfanyl)-[9,9']bifluorenyl

Perbenzoic acid

Downstream raw materials:

9,9'-bifluorenyl

9-fluorenone oxime

2-fluoren-9-ylidenaminooxy-propionic acid

9-phenylbutadiynyl-fluoren-9-ol

Refernces

• 1、 Davis et al.. "". . p. 2264. Retrieved 1969.
• 2、 Richardson,Hodge. "". . p. 1216. Retrieved 1970.
• 3、 Ghera et al.. "". . p. 3627,3628, 3630. Retrieved 1976.
• 4、 Reddy, Sabbasani Rajasekhara,Titu, Devamani,Chadha, Anju. "A novel method for monitoring the transesterification reaction of oil in biodiesel production by estimation of glycerol". . p. 747 - 754. Retrieved 2010.
• 5、 Schoenberg,Awad. "-". . p. 788. Retrieved 1950.
• 6、 Huang, Tao,Zhao, Xianghu,Ji, Xinfei,Wu, Wei,Cao, Song. "Synthesis of fluorovinyl pyrazolyl (thio)ethers by the reaction of gem-difluoroalkenes with pyrazolin-5-ones (thiones)". . p. 61 - 68. Retrieved 2016.
• 7、 Murahashi,Oda,Naota,Kuwabara. "Ruthenium-catalyzed cytochrome P-450 type oxidation of alkanes with alkyl hydroperoxides". . p. 1299 - 1302. Retrieved 1993.
• 8、 Pfeiffer, Juergen,Nieger, Martin,Doetz, Karl Heinz. "Tetracyclic arenes by benzannulation of tricyclic carbene complexes of chromium with alkynes: Chemo-, regio-, and stereoselectivity". . p. 1843 - 1857. Retrieved 1998.
• 9、 Hoz, Shmaryahu,Perach, Sara Sima. "Substituent and pH Effects on the Hydrolysis Modes of 9-(dinitromethyl)-9-alkoxylfluorenes". . p. 4056 - 4059. Retrieved 1982.
• 10、 Metz. "-". . p. 612. Retrieved 1972.