FLUORENONE

Fluorenone is an important tricyclic aromatic intermediate valued for its versatility in specialty organic chemistry and advanced material synthesis.
Fluorenone's conjugated molecular framework supports applications in luminescent compounds, electronic materials, molecular probes, and customized fluorene-based structures.
The combination of structural rigidity and accessible carbonyl functionality makes fluorenone a practical precursor for both research-scale development and industrial chemical production.

CAS Number: 486-25-9
EC Number: 207-630-7
Molecular Formula: C13H8O
Molecular Weight: 180.206 g/mol

Synonyms: 9-Fluorenone, 486-25-9, 9H-Fluoren-9-one, Fluoren-9-one, FLUORENONE, Diphenylene ketone, 9-Oxofluorene, DTXSID6049307, AZ9T83S2AQ, CHEBI:17922, NSC-5181, DTXCID5029263, RefChem:6603, 207-630-7, C13H8O, MFCD00001141, 9H-Fluorene-9-one, AI3-00858, FLUORENONE [HSDB], bmse000521, WLN: L B656 HVJ, CHEMBL571655, Tox21_202919, c0390, CX1121, AKOS000118911, NCGC00336203-01, HY-32181, EU-0084734, F0021, AB00376854-04, Q421328, CCRIS 593, HSDB 5490, NSC 5181, EINECS 207-630-7, UNII-AZ9T83S2AQ, AMY818, 9-fluoreneone, 9H-fluoren9-one, 9-Fluorenone, 98%, SCHEMBL18844, SCHEMBL31884, SCHEMBL693395, orb3025969, orb3029398, SCHEMBL1818666, SCHEMBL1929100, SCHEMBL2077973, SCHEMBL9799712, SCHEMBL29378679, NSC5181, PDK0234, HMS1783A21, BDBM50303915, SBB056398, STK755582, AC-4873, EBC-610767, FF00182, MSK001423-100M, PS-5769, MSK001423-1000M, NCGC00260465-01, CAS-486-25-9, DB-029404, ST4029931, CS-0001481, NS00014587, 9-Fluorenone Solution in Methanol, 100ug/mL, EN300-17413, 9-Fluorenone Solution in Methanol, 1000ug/mL, C06712, AH-034/05416008, F095005, SR-01000515877, SR-01000515877-1, Z56926556, InChI=1/C13H8O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8, 207-630-7, 486-25-9, 9-Fluorenone, 9H-Fluoren-9-on, 9H-Fluoren-9-one, 9H-Fluorén-9-one, Diphenylene ketone, fluoren-9-one, Fluorenone, 137219-34-2, 207-630-7MFCD00001141, 328-90-5, 86-28-2, 9-ethylcarbazole, 9-Fluore, 9-Fluorenone-d8, 9-Oxo-9H-fluorene, 9-Oxofluorene, 952573-42-1, 98%, 9H-Fluoren-9-one-D4, 9H-Fluorene-9-one, Fluorexon, Heat shock protein HSP 90-α, Heat shock protein HSP 90-β, HS90A_HUMAN, HS90B_HUMAN

Fluorenone is an important intermediate for organic synthesis.
Fluorenone 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%.
    
Fluorenone is the simplest member of the class fluoren-9-ones that is 9H-fluorene bearing an oxo substituent at position 9.
Fluorenone has a role as a fungal xenobiotic metabolite.

Fluorenone is used in the preparation of antimalarial drugs.
Fluorenone is a fluorene derivative.
Further, Fluorenone is used in functional polymer and in dyes.

Fluorenone is an aromatic ketone with the molecular formula C13H8O, characterized by a rigid tricyclic fluorene framework containing a central carbonyl group.
Fluorenone typically appears as a yellow crystalline solid and is widely used as an intermediate in organic synthesis, pharmaceuticals, dyes, pigments, optical materials, and specialty chemicals.
Fluorenone's conjugated ring system and reactive ketone functionality make fluorenone a valuable building block for preparing functional aromatic compounds, fluorescent materials, and advanced molecular structures.

Fluorenone is an organic compound with the chemical formula (C6H4)2CO, and is a ketone with a fluorene moiety.
Fluorenone is a bright yellow, fluorescent solid.

Fluorenone is an organic compound characterized by its structure, which consists of a fused ring system featuring a ketone functional group.
Fluorenone is a derivative of fluorene, where one of the methylene groups is replaced by a carbonyl group (C=O).

Fluorenone typically appears as a white to pale yellow crystalline solid and is known for its aromatic properties.
Fluorenone is relatively stable and exhibits moderate solubility in organic solvents such as ethanol and ether, while being less soluble in water due to its hydrophobic nature.

Fluorenone has applications in organic synthesis, serving as an intermediate in the production of various dyes and pharmaceuticals.
Additionally, fluorenone can undergo various chemical reactions, including reduction to form fluorenol or further reactions to yield other derivatives.
Fluorenone's unique photophysical properties make it of interest in materials science, particularly in the development of organic light-emitting diodes (OLEDs) and other optoelectronic devices.

Uses of Fluorenone:
Fluorenone is used as an intermediate and a reagent (Oppenauer oxidation).
Fluorenone is used as a chemical intermediate in the synthesis of: 2-methyl-3-phenylbenzyl alcohol; 2,3,7-trinitrofluorenone.

Fluorenone is used in the preparation of antimalarial drugs.
Fluorenone is a fluorene derivative.
Further, Fluorenone is used in functional polymer and in dyes.

Fluorenone is widely used as an intermediate in the synthesis of pharmaceuticals, fine chemicals, and specialty organic compounds.
Fluorenone serves as a precursor for dyes, pigments, fluorescent materials, and optical brightening agents.

Fluorenone derivatives are used in the development of electronic, photochemical, and optoelectronic materials.
Fluorenone is employed as a building block in organic synthesis for producing substituted fluorene and fluorenone compounds.

Fluorenone is also used in research related to polymers, molecular probes, sensors, and advanced functional materials.
Fluorenone's rigid aromatic framework and reactive carbonyl group make fluorenone valuable in laboratory synthesis and high-value chemical manufacturing.

Industry Uses:
Intermediate

Applications of Fluorenone:
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.
Fluorenone also acts as a sensitizer in the formation of picene via photosensitization of 1,2-di(1-naphthyl)ethane.
Several substituted fluorenones are biologically active as antibiotic, anticancer, antiviral, or neuromodulatory compounds.

Some substituted azafluorenones are biologically active, such as the naturally occurring antimicrobial compound onychine (1-methyl-4-azafluorenone).
Fluorenone 1,8-diazafluoren-9-one is used for fingerprint detection.

Drugs:

Fluorenone is used to synthesize:
A drug called IPS-339 [60979-28-4].
An analog of 2-MDP.
Paranyline.
Via a Beckmann rearrangement, phenanthridone.
Fluorenone is used in the synthesis of fantridone.

Synthesis and reactions of Fluorenone:

Fluorenone is synthesised by aerobic oxidation of fluorene:
(C6H4)2CH2 + O2 → (C6H4)2CO + H2O

Fluorenone sustains up to four nitro groups giving 2,4,5,7-tetranitrofluorenone.

Stability and Reactivity of Fluorenone:

Chemical stability:
Fluorenone is stable under normal ambient temperatures and recommended storage conditions.

Reactivity:
No significant reactivity is expected under normal conditions of handling and use.

Conditions to avoid:
Avoid excessive heat, ignition sources, dust formation, and contact with incompatible materials.

Incompatible materials:
Avoid strong oxidizing agents.

Hazardous decomposition products:
Thermal decomposition or combustion may generate carbon monoxide, carbon dioxide, and irritating vapors.

Handling and Storage of Fluorenone:

Safe handling:
Avoid inhalation of dust and unnecessary contact with the skin, eyes, and clothing.
Use adequate ventilation and minimize dust generation.

Storage conditions:
Keep the container tightly closed in a cool, dry, and well-ventilated place away from heat and incompatible materials.

First Aid Measures of Fluorenone:

Inhalation:
Move the affected person to fresh air and obtain medical attention if symptoms develop.

Skin contact:
Remove contaminated clothing and wash the affected area thoroughly with soap and water.

Eye contact:
Rinse cautiously with plenty of water for several minutes and obtain medical attention if irritation persists.

Ingestion:
Rinse the mouth with water and obtain medical advice if discomfort occurs.

Firefighting Measures of Fluorenone:

Suitable extinguishing media:
Use water spray, dry chemical, carbon dioxide, or suitable foam according to surrounding fire conditions.

Protective equipment:
Firefighters should wear full protective equipment and self-contained breathing apparatus.

Hazardous combustion products:
Combustion may generate carbon monoxide, carbon dioxide, and irritating fumes.

Accidental Release Measures of Fluorenone:

Personal precautions:
Ensure adequate ventilation, avoid dust formation, and wear suitable personal protective equipment.

Cleanup methods:
Carefully sweep or collect spilled material into a suitable closed container while minimizing airborne dust.

Environmental precautions:
Prevent release into surface water, drains, and sewer systems.

Exposure Controls/Personal Protection of Fluorenone:

Engineering controls:
Provide adequate ventilation and ensure that eyewash stations and safety showers are readily accessible.

Eye protection:
Wear suitable safety glasses or chemical protective goggles.

Hand protection:
Wear appropriate protective gloves.

Body protection:
Use suitable protective clothing to minimize skin exposure.

Respiratory protection:
Respiratory protection is generally not required under normal conditions with adequate ventilation; use a suitable particulate filter when significant dust is generated.

Identifiers of Fluorenone:
CAS: 486-25-9
Molecular Formula: C13H8O
Molecular Weight (g/mol): 180.206
MDL Number: MFCD00001141
InChI Key: YLQWCDOCJODRMT-UHFFFAOYSA-N
PubChem CID: 10241
ChEBI: CHEBI:17922
IUPAC Name: fluoren-9-one
SMILES: C1=CC=C2C(=C1)C3=CC=CC=C3C2=O

CAS: 486-25-9
IUPAC Name: 9H-fluoren-9-one
Molecular Formula: C13H8O
InChI Key: YLQWCDOCJODRMT-UHFFFAOYSA-N
SMILES: O=C1C2=CC=CC=C2C2=CC=CC=C12
Molecular Weight (g/mol): 180.21
Synonym: fluorenone diphenylene ketone ccris 593

Product Number: F0021
Purity / Analysis Method: >98.0%(GC)
Molecular Formula / Molecular Weight: C13H8O = 180.21
Physical State (20 deg.C): Solid
Storage Temperature: Room Temperature (Recommended in a cool and dark place, <15°C)
CAS RN: 486-25-9
Reaxys Registry Number: 1636531
PubChem Substance ID: 87569834
SDBS (AIST Spectral DB): 2223
MDL Number: MFCD00001141

CAS Number: 486-25-9
ChEBI: CHEBI:17922
ChEMBL: ChEMBL571655
ChemSpider: 9824
ECHA InfoCard: 100.006.937
KEGG: C06712
PubChem CID: 10241
UNII: AZ9T83S2AQ
CompTox Dashboard (EPA): DTXSID6049307
InChI: InChI=1S/C13H8O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8H
Key: YLQWCDOCJODRMT-UHFFFAOYSA-N
InChI: InChI=1/C13H8O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8H
Key: YLQWCDOCJODRMT-UHFFFAOYAR
SMILES: c1ccc2c(c1)-c3ccccc3C2=O

Empirical Formula (Hill Notation): C13H8O
CAS Number: 486-25-9
Molecular Weight: 180.20
UNSPSC Code: 12352100
NACRES: NA.22
PubChem Substance ID: 24894771
EC Number: 207-630-7
Beilstein/REAXYS Number: 1636531
MDL Number: MFCD00001141
Assay: 98%

Quality Segment: 200
Assay: 98%
Boiling Point: 342 °C (lit.)
Melting Point: 80-83 °C (lit.)
Functional Group: ketone
SMILES String: O=C1c2ccccc2-c3ccccc13
InChI: 1S/C13H8O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8H
InChI Key: YLQWCDOCJODRMT-UHFFFAOYSA-N

Properties of Fluorenone:
Chemical Formula: C13H8O
Molar Mass: 180.206 g·mol−1
Appearance: Yellow solid
Density: 1.130 g/cm3 (99 °C)
Melting Point: 84.0 °C (183.2 °F; 357.1 K)
Boiling Point: 341.5 °C (646.7 °F; 614.6 K)
Solubility in Water: Insoluble
Solubility: soluble in alcohol, acetone, benzene
Solubility: very soluble in ether, toluene
log P: 3.58
Magnetic Susceptibility (χ): −99.4·10−6 cm3/mol
Refractive Index (nD): 1.6309

Molecular Weight: 180.20 g/mol
XLogP3: 3.6
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 0
Exact Mass: 180.057514874 Da
Monoisotopic Mass: 180.057514874 Da
Topological Polar Surface Area: 17.1 Ų
Heavy Atom Count: 14
Complexity: 222
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of Fluorenone:
Appearance: Light yellow to Yellow to Green powder to lump
Purity (GC): min. 98.0 %
Melting Point: 82.0 to 86.0 °C
Solubility in Methanol: almost transparency
NMR: confirm to structure

Melting Point: 81°C to 85°C
GC: >=99.0 %
Appearance (Color): Yellow
Appearance (Form): Crystalline powder or flakes
Infrared Spectrum: Conforms

Melting Point: 82°C to 85°C
Density: 0.9
Boiling Point: 342°C
Flash Point: 163°C (325°F)
Assay Percent Range: 98%
Quantity: 100 g
Beilstein: 1636531
Solubility Information: Soluble in water,alcohol,acetone,ether and benzene.
Formula Weight: 180.21
Percent Purity: ≥98%
Chemical Name or Material: 9-Fluorenone

Related compounds of Fluorenone:
Fluorene
1,8-Diazafluoren-9-one

Names of Fluorenone:

Preferred IUPAC name:
9H-Fluoren-9-one

Other names:
9-Fluorenone
9-Oxofluorene
Diphenylene ketone