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Fluorene ( CASNO:86-73-7 )

Identification and Related Records
Name:
Fluorene
CAS Registry number:
86-73-7
Synonyms:
Fluorene(8CI)
2,2'-Methylenebiphenyl
Diphenylenemethane
Methane, diphenylene-
NSC6787
o-Biphenylenemethane
EINECS(EC#):
201-695-5
Molecular Formula:
C13H10
Molecular Weight:
166.22
Inchi:
InChI=1/C13H10/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)12/h1-8H,9H2
InChIKey:
NIHNNTQXNPWCJQ-UHFFFAOYSA-N
Canonical SMILES:
C1C2=CC=CC=C2C3=CC=CC=C31
Chemical and Physical Properties
Appearance:
white flakes
Density:
1.203
Melting Point:
112-116℃
Boiling Point:
298℃
Refractive Index:
1.645
Flash Point:
151℃
Water:
insoluble
Solubilities:
Insoluble AUTOIGNITION
Color/Form:
DAZZLING WHITE LEAFLETS OR FLAKES FROM ALCOHOL
SMALL, WHITE, CRYSTALLINE PLATES; FLUORESCENT WHEN IMPURE
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents.
HS Code:
29029080
Storage temp:
APPROX 4°C
Spectral properties:
MAX ABSORPTION (CHLOROFORM): 266 NM (LOG E= 4.3); 290 NM (LOG E= 3.8); 301 NM (LOG E= 4.0)
SADTLER REF NUMBER: 7540 (IR, PRISM); 240 (IR, GRATING); 2114 (UV); 288 (NMR)
Intense mass spectral peaks: 166 m/z (100%), 165 m/z (80%), 167 m/z (15%), 163 m/z (12%)
IR: 6251 (Coblentz Society Spectral Collection)
UV: 5-350 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
MASS: 127 (Aldermaston, Eight Peak Index of Mass Spectra, UK)
Computed Properties:
Molecular Weight:166.2185 [g/mol]
Molecular Formula:C13H10
XLogP3:4.2
H-Bond Donor:0
H-Bond Acceptor:0
Rotatable Bond Count:0
Exact Mass:166.07825
MonoIsotopic Mass:166.07825
Topological Polar Surface Area:0
Heavy Atom Count:13
Formal Charge:0
Complexity:165
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
Feature 3D Ring Count:3
Effective Rotor Count:0.2
Conformer Sampling RMSD:0.4
CID Conformer Count:1
Safety and Handling
Hazard Codes:
Xi: Irritant;Xn: Harmful;T: Toxic;F: Flammable;N: Dangerous for the environment;
Risk Statements:
R50/53
Safety Statements:
S24/25
HazardClass:
9
Hazard Note:
Harmful
Safety:
Hazard Codes:DangerousNToxicTFlammableFIrritantXiHarmfulXn
Risk Statements: 50/53-39/23/24/25-23/24/25-11-67-65-38-36/38-36/37/38 
R50/53: Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
R39: Danger of very serious irreversible effects
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed
R11: Highly flammable
R67: Vapours may cause drowsiness and dizziness
R65: Harmful: may cause lung damage if swallowed
R38: Irritating to skin
R36/38: Irritating to eyes and skin
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 60-61-24/25-45-36/37-16-7-62-33-24-22-36/37/39-27-26 
S60: This material and its container must be disposed of as hazardous waste
S61: Avoid release to the environment. Refer to special instructions / safety data sheets
S24/25: Avoid contact with skin and eyes
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37: Wear suitable protective clothing and gloves
S16: Keep away from sources of ignition
S62: If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label
S33: Take precautionary measures against static discharges
S24: Avoid contact with skin
S22: Do not breathe dust
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
S27: Take off immediately all contaminated clothing
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
RIDADR: UN 3077 9/PG 3
WGK Germany: 3
RTECS: LL5670000
Hazard Note: Harmful
HazardClass 9
PackingGroup: III
HS Code: 29029080
PackingGroup:
III
Cleanup Methods:
The particle-bound portion of polycyclic aromatic hydrocarbons (PAH) can be removed by sedimentation, flocculation, and filtration processes. The remaining ... dissolved polynuclear aromatic hydrocarbons usually requires oxidation for partial removal/transformation. /Polynuclear aromatic hydrocarbons/
Transport:
UN 3077
Formulations/Preparations:
GRADES: TECHNICAL; 98% PURE
Fluorene (technical) 90% (min)
Other Preventative Measures:
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Specification:
Personal Protection:
Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to prevent skin exposure.
Fire Fighting: Wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. To extinguish fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. Use agent most appropriate to extinguish fire.
Use and Manufacturing
Use and Manufacturing:
Methods of Manufacturing

FROM ACETYLENE & HYDROGEN IN RED-HOT TUBE; FROM CHARCOAL BY BOILING WITH FUMING NITRIC ACID; FROM 2,2'-DIBROMODIPHENYLMETHANE ON BOILING WITH HYDRAZINE HYDRATE IN PRESENCE OF PALLADIUM.
BY REDUCTION OF DIPHENYLENE KETONE WITH ZINC
U.S. Imports

(1972) 2.85X10+6 GRAMS
(1975) 4.49X10+4 GRAMS
(1984) 9.08X10+3 g
U.S. Production

(1972) NOT PRODUCED COMMERCIALLY IN USA
(1975) NOT PRODUCED COMMERCIALLY IN USA
NO /COMMERCIAL USA / PRODUCTION OF THIS COMPOUND
Consumption Patterns

100% AS A CHEMICAL INTERMEDIATE IN VARIOUS APPLICATIONS
Usage:
Chemical intermediate in numerous misc applications & in formation of polyradicals for resins.
Sampling Procedures:
NIOSH Method 5515. Analyte: Fluorene. MATRIX: Air. Sampler: Filter plus sorbent (2 um, 37-mm polytetrafluoroethylene plus washed XAD-2, 100 mg/50 mg). Flow Rate: 2 l/min: Sample Size: 400 liters. SHIPMENT: Transfer filters to culture tubes; wrap sorbent and culture tubes in aluminum foil; ship @ 0 deg C. Sample Stability: Unknown; protect from heat and ultraviolet radiation.
NIOSH Method 5506. Analyte: Fluorene. MATRIX: Air. Sampler: Filter plus sorbent (2 um, 37 mm polytetra fluoroethylene plus washed XAD-2, 100 mg/50 mg). Flow Rate: 2 l/min. Sample Size: 400 liters. SHIPMENT: Transfer filters to culture tubes wrap sorbent and culture tubes in aluminum foil; ship @ 0 deg C. Stability: Unknown; protect from heat and ultraviolet radiation.
Biomedical Effects and Toxicity
Pharmacological Action:
- Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.
Biomedical Effects and Toxicity:
THERE WERE SPECIES DIFFERENCES IN EXCRETION OF AN IP DOSE OF (14)C FLUORENE. GUINEA PIGS ELIMINATED (14)C MORE RAPIDLY THAN RATS OR RABBITS & AFTER 12 HR, HAD EXCRETED 53% IN URINE WHEREAS OTHER SPECIES HAD EXCRETED 12% & 20% RESPECTIVELY. IN 48 HR, IN URINE & FECES RESPECTIVELY, GUINEA PIGS EXCRETED 82% & 6%, RATS EXCRETED 57% & 16% & RABBITS EXCRETED 39% & 1%. 24 HR AFTER DOSE TO RATS, INTESTINAL TRACT CONTAINED 14% OF THE (14)C & SINCE THIS HAD NOT ALTERED 24 HR LATER, ENTERO-HEPATIC CIRCULATION OF FLUORENE &/OR ITS METABOLITES MAY HAVE OCCURRED TO MAINTAIN THOSE LEVELS. HOWEVER, SLOW RELEASE OF 14(C) FROM INJECTION SITE PROVIDES AN ALTERNATIVE EXPLANATION.
Environmental Fate and Exposure Potential
Environmental Fate/Exposure Summary:
Polycyclic aromatic hydrocarbons with 4 or less aromatic rings are degraded by microbes and are readily metabolized by multicellular organisms; biodegradation may be the ultimate fate process. /Polycyclic aromatic hydrocarbons/
Biodegradation is probably slower in the aquatic system than in the soil, and biodegradation may be much more important in those aquatic systems which are chronically affected by contamination. /Polycyclic aromatic hydrocarbons/
In microbial degradation studies conducted in sandy material, fluorene and other PAHs degraded to an average of 80%(1); in sterile controls, fluorene did not degrade suggesting microbial activity as the route of degradation(1). A review of environmental fate for fluorene has reported a fluorene biotransformation rate constant of 0.0062-0.01/hr(2); this corresponds to a half-life of 2.9-4.6 days(SRC). In a 7 day static incubation study using a sewage seed (followed by three weekly subculture inoculations for a total of 28 days of incubation), 65-82% of initial fluorene (5 and 10 ppm) was degraded after 7 days and 45-77% (of total additions) was degraded after 28 days(3); fluorene was classified as significantly degraded with gradual microbial adaptation(3). In biodegradation screening studies using subsurface soil from a contaminated creosote site, >92% of initial fluorene degraded within 1 week of incubation(4); in autoclaved soil, the degradation rate fell to 3.4% per week(4); using soil from a pristine site, the degradation rate was not statistically different between autoclaved and non-autoclaved soil suggesting that microbial adaptation to fluorene is important in subsurface regions(4).
In biodegradation tests using groundwater from a moderately contaminated well, fluorene degraded at a rate of 33-54% per week under conditions of dissolved oxygen addition and/or nutrient addition(1); no degradation occurred in sterile controls or in tests where limited oxygen was available(1). In a pilot-plant experimental system (simulating a waste treatment facility), 34-39% of influent fluorene was removed via biodegradation (the remainder was removed via strip loss (5-10%) and adsorption to sludge)(2). In a shake-flask screening study using creosote-contaminated soil as inoculum, 99% of initial fluorene was degraded after a 14 day incubation period(3); in sterile controls, only 15% of initial fluorene was lost(3). In river die-away tests using two natural river waters, little or no fluorene was degraded to CO2 (14-CO2 radio-labelled measurement) over a 24 hr incubation period(4).
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