86-73-7 Usage
Chemical Description
Fluorene is a polycyclic aromatic hydrocarbon with the chemical formula C13H10.
Chemical Properties
Different sources of media describe the Chemical Properties of 86-73-7 differently. You can refer to the following data:
1. white crystals
2. Fluorene, when pure, is found as dazzling white flakes or small, crystalline plates. It is fluorescent
when impure. Polycyclic aromatic hydrocarbons (PAHs)
are compounds containing multiple benzene rings and are
also called polynuclear aromatic hydrocarbons.
Physical properties
Small white leaflets or crystalline flakes from ethanol. Fluorescent when impure.
Uses
Different sources of media describe the Uses of 86-73-7 differently. You can refer to the following data:
1. Polycyclic aromatic hydrocarbons as micropollutants.
2. Fluorene was used study the extraction of specific, semiconducting single-wall carbon nanotubes (SWCNTs).
Definition
ChEBI: An ortho-fused tricyclic hydrocarbon that is a major component of fossil fuels and their derivatives
Synthesis Reference(s)
Journal of the American Chemical Society, 73, p. 2656, 1951 DOI: 10.1021/ja01150a069Synthetic Communications, 26, p. 1467, 1996 DOI: 10.1080/00397919608003512The Journal of Organic Chemistry, 37, p. 1273, 1972 DOI: 10.1021/jo00973a049
General Description
White leaflets. Sublimes easily under a vacuum. Fluorescent when impure.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as Fluorene, and strong oxidizing agents. They can react exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction.
Hazard
Questionable carcinogen.
Health Hazard
Different sources of media describe the Health Hazard of 86-73-7 differently. You can refer to the following data:
1. Acute toxicity in animals is very low. AnLD50 (intraperitoneal) in mice is 2000 mg/kg.Carcinogenicity of this compound in animalsis not well established. It tested negative in ahistidine reversion–Ames test.
2. ACUTE/CHRONIC HAZARDS: Fire hazards: Slight, when exposed to heat or flame.
Potential Exposure
Fluorene is used in resins, dyes, and is
a chemical intermediate.
Source
Fluorene was detected in groundwater beneath a former coal gasification plant in Seattle,
WA at a concentration of 140 μg/L (ASTR, 1995). Present in diesel fuel and corresponding aqueous phase (distilled water) at concentrations of 350 to 900 mg/L and 12 to 26 g/L,
respectively (Lee et al., 1992). Schauer et al. (1999) reported fluorene in diesel fuel at a
concentration of 52 g/g and in a diesel-powered medium-duty truck exhaust at an emission rate of
34.6 g/km. Diesel fuel obtained from a service station in Schlieren, Switzerland contained fluorene
at an estimated concentration of 170 mg/L (Schluep et al., 2001).
Based on laboratory analysis of 7 coal tar samples, fluorene concentrations ranged from 1,100 to
12,000 ppm (EPRI, 1990). Lao et al. (1975) reported a fluorene concentration of 27.39 g/kg in a
coal tar sample. Detected in 1-yr aged coal tar film and bulk coal tar at an identical concentration
of 4,400 mg/kg (Nelson et al., 1996). A high-temperature coal tar contained fluorene at an average
concentration of 0.64 wt % (McNeil, 1983). Identified in high-temperature coal tar pitches at
concentrations ranging from 800 to 4,000 mg/kg (Arrendale and Rogers, 1981). Lee et al. (1992a)
equilibrated 8 coal tars with distilled water at 25 °C. The maximum concentration of fluorene
observed in the aqueous phase was 0.3 mg/L.
Fluorene was detected in asphalt fumes at an average concentration of 34.95 ng/m3 (Wang et al.,
2001).
Nine commercially available creosote samples contained fluorene at concentrations ranging
from 19,000 to 73,000 mg/kg (Kohler et al., 2000).
Thomas and Delfino (1991) equilibrated contaminant-free groundwater collected from
Gainesville, FL with individual fractions of three individual petroleum products at 24–25 °C for
24 h. The aqueous phase was analyzed for organic compounds via U.S. EPA approved test method
625. Average fluorene concentrations reported in water-soluble fractions of unleaded gasoline,
kerosene, and diesel fuel were 1, 3, and 10 μg/L, respectively.
Fluorene was detected in soot generated from underventilated combustion of natural gas doped
with toluene (3 mole %) (Tolocka and Miller, 1995).
Schauer et al. (2001) measured organic compound emission rates for volatile organic
compounds, gas-phase semi-volatile organic compounds, and particle-phase organic compounds
from the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emission
rates of fluorene were 4.44 mg/kg of pine burned, 3.83 mg/kg of oak burned, and 2.613 mg/kg of
eucalyptus burned.
California Phase II reformulated gasoline contained fluorene at a concentration of 4.35 mg/kg.
Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic
converters were 9.72 and 358 μg/km, respectively (Schauer et al., 2002).
Under atmospheric conditions, a low rank coal (0.5–1 mm particle size) from Spain was burned
in a fluidized bed reactor at seven different temperatures (50 °C increments), beginning at 650 °C.
The combustion experiment was also conducted at different amounts of excess oxygen (5 to 40%)
and different flow rates (700 to 1,100 L/h). At 20% excess oxygen and a flow rate of 860 L/h, the
amount of fluorine emitted ranged from 850.7 ng/kg at 950 °C to 3,632.8 ng/kg at 750 °C. The
greatest amount of PAHs emitted were observed at 750 °C (Mastral et al., 1999).
In one study, fluorene comprised about 7.6% of polyaromatic hydrocarbons in creosote (Grifoll
et al., 1995).
Identified as an impurity in commcerially available acenaphthene (Marciniak, 2002).
Typical concentration of fluorene in a heavy pyrolysis oil is 1.6 wt % (Chevron Phillips, May
2003).
Environmental fate
Biological. Fluorene was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum. Significant biodegradation with gradual adaptation was observed.
At concentrations of 5 and 10 mg/L, biodegradation yields at the end of 4 wk of incubation were
77 and 45%, respectively (Tabak et al., 1981).
Photolytic. Fluorene reacts with photochemically produced OH radicals in the atmosphere. The
atmospheric half-life was estimated to range from 6.81 to 68.1 h (Atkinson, 1987). Behymer and
Hites (1985) determined the effect of different substrates on the rate of photooxidation of fluorene
(25 μg/g substrate) using a rotary photoreactor. The photolytic half-lives of fluorene using silica
gel, alumina, and fly ash were 110, 62, and 37 h, respectively. Gas-phase reaction rate constants
for OH radicals, NO3 radicals, and ozone at 24 °C were 1.6 x 10-11, 3.5 x 10-15, and <2 x 10-19 in
cm3/molecule?sec, respectively (Kwok et al., 1997).
Chemical/Physical. Oxidation by ozone to fluorenone has been reported (Nikolaou, 1984).
Chlorination of fluorene in polluted humus poor lake water gave a chlorinated derivative
tentatively identified as 2-chlorofluorene (Johnsen et al., 1989). This compound was also
identified as a chlorination product of fluorene at low pH (<4) (Oyler et al., 1983). It was
suggested that the chlorination of fluorene in tap water accounted for the presence of
chlorofluorene (Shiraishi et al., 1985).
Shipping
UN3077 Environmentally hazardous substances,
solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous haz ardous material, Technical Name Required.
Purification Methods
Purify fluorene by chromatography of CCl4 or pet ether (b 40-60o) solution on alumina, with *benzene as eluent. Crystallise it from 95% EtOH, 90% acetic acid and again from EtOH. Crystallisation using glacial acetic acid retains an impurity which is removed by partial mercuration and precipitation with LiBr [Brown et al. J Am Chem Soc 84 1229 1962]. It has also been crystallised from hexane, or *benzene/EtOH, distilled under vacuum and purified by zone refining. [Gorman et al. J Am Chem Soc 107 4404 1985, Beilstein 5 IV 2142.]
Incompatibilities
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explo sions. Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. Compound can react exo thermically with bases and with diazo compounds.
Substitution at the benzene nucleus occurs by halogenation
(acid catalyst), nitration, sulfonation, and the Friedel Crafts
reaction.
Waste Disposal
Persons in charge of vessels
or facilities are required to notify the National Response
Center (NRC) immediately when there is a release of this
designated hazardous substance, in an amount equal to or
greater than its RQ listed above. The toll free number of
the NRC is (800) 424-8802; In the Washington D.C. metro politan area call (202) 426-2675. The rule for determining
when notification is required is stated in 40 CFR 302.4
(Section IV. D.3.b).
Check Digit Verification of cas no
The CAS Registry Mumber 86-73-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 6 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 86-73:
(4*8)+(3*6)+(2*7)+(1*3)=67
67 % 10 = 7
So 86-73-7 is a valid CAS Registry Number.
InChI:InChI=1/C13H10/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)12/h1-8H,9H2
86-73-7Relevant articles and documents
Synthesis and thermal rearrangement of pentacyclo[6.5.0.04,12.05,10.09,13]trideca-2,6-diene
Marchand,Rajapaksa,Vidyasagar,Eckrich,Kumar
, p. 11937 - 11944 (1995)
Pentacyclo[6.5.0.04,12.05,10.09,13]trideca-2,6-diene (16) has been synthesized in five steps from 1-hydroxyhexacyclo[6.5.0.02,6.03,11.05,10.09,12]trideca n-7-one (10). Compound 16 undergoes thermal rearrangement to pentacyclo[7.4.0.02,6.03,11.05,10]trideca-7,12-diene (i.e. '[2.2.1]triblattadiene', 19). The intermediacy of cis,cisoid,cis-tricyclo[7.4.0.02,7[trideca-3,5,10,12-tetraene (18) in the thermal rearrangement of 16 was inferred via analysis of the 1H NMR spectrum of partially rearranged 16 and subsequently was further established via the results of a trapping experiment (i.e., fluorene was produced when thermal rearrangement of 16 was performed in the presence of 10% Pd/C).
Hydrogenation of 9-pyridylmethylene- and 9-benzylidene(aza)fluorenes in the presence of rhenium heptasulfide
Kolyadina,Soldatenkov,Ryashentseva,Prostakov
, p. 171 - 173 (1996)
Hydrogenation of 9-pyridylmethylene(aza)fluorenes and 9-benzylidene-4-azafluorene at 250°C and pH2 = 130 atm in the presence of Re2S7 as a catalyst occurs preferably at the exocyclic double bond of the fulvene fragment to yield pyridyl-9-(aza)fluorenylmethanes.
Surface confined ketyl radicals via samarium(II)-grafted mesoporous silicas [3]
Nagl, Iris,Widenmeyer, Markus,Grasser, Stefan,Koehler, Klaus,Anwander, Reiner
, p. 1544 - 1545 (2000)
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Palladium-Catalyzed Coupling of Biphenyl-2-yl Trifluoromethanesulfonates with Dibromomethane to Access Fluorenes
Pan, Shulei,Zhang, Yanghui,Zhu, Qiongqiong
, (2022/03/27)
A facile and efficient method has been developed for the synthesis of fluorenes by Pd-catalyzed C-H alkylation of biphenyl-2-yl trifluoromethanesulfonates. The trifluoromethanesulfonates are more readily available and more environmentally benign than biphenyl iodides, and are advantageous substrates for traceless directing-groupassisted C-H activation. The reaction generates C,C-palladacycles as the key intermediates that form two C(sp2)-C(sp3) bonds through reaction with CH2Br2. The reaction tolerates various functional groups, permitting easy access to a range of fluorene derivatives.
Pd-Catalyzed Assembly of Fluoren-9-ones by Merging of C-H Activation and Difluorocarbene Transfer
Liu, Xiaobing,Sheng, Heyun,Zhou, Yao,Song, Qiuling
supporting information, p. 2543 - 2547 (2021/05/05)
We disclose a novel Pd-catalyzed assembly of fluoren-9-ones by merging of C-H activation and difluorocarbene transfer. ClCF2COONa served as a difluorocarbene precursor to be harnessed as a carbonyl source in this transformation. The current protocol enables us to afford fluoren-9-ones in high yields with excellent functional group compatibility, which also represents the first example of using difluorocarbene as a coupling partner in transition-metal-catalyzed C-H activation.
Palladium-catalyzed intramolecular aromatic C-H acylation of 2-arylbenzoyl fluorides
Hayakawa, Kazuki,Ikai, Kana,Ogiwara, Yohei,Sakai, Norio,Sakurai, Yuka
, p. 1882 - 1893 (2021/08/13)
The catalytic intramolecular cyclization of acyl fluorides using a Pd(OAc)2/PCy3 system is described. A wide range of 2-arylbenzoyl fluoride derivatives can be used as fluorenone precursors and the reaction proceeds via an intramolecular coupling between aromatic C-H bonds with acyl C-F bonds. The reaction can be applied to the synthesis of indenofluorenedione derivatives and to the construction of other molecules with fivemembered rings.
