Fluorenone is soluble in a wide range of organic solvents (solvents that are carbon-hydrogen based) including things like chloroform, methanol Methanol, also known as methyl alcohol among others, is a chemical with the formula CH₃OH. Methanol acquired the name wood alcohol because it was once produced chiefly by the destructive distillation of wood. Today, methanol is mainly produced industrially by hydrogenation of … Dichloromethane is an organochlorine compound with the formula CH₂Cl₂. This colorless, volatile liquid with a moderately sweet aroma is widely used as a solvent. Although it is not miscible with water, it is polar, and miscible with many organic solvents. Acetonitrile is the chemical compound with the formula CH₃CN. This colourless liquid is the simplest organic nitrile. It is produced mainly as a byproduct of acrylonitrile manufacture. It is used as a polar aprotic solvent in organic synthesis and in the purification of butadiene.Methanol
Dichloromethane
Acetonitrile
What is the solubility of fluorene?
Solubility of Fluorene. In chemistry, we sometimes use the phrase 'like dissolves like.' What this simple but powerful phrase means is that, in general, substances that are similar to one another in terms of their polarity should mix well (or be soluble) with one another.
What is fluorene?
Fluorene is a member of a group of chemicals called polycyclic aromatic hydrocarbons (PAHs). Fluorene occurs in fossil fuels. Its release to the environment is wide spread since it is a ubiquitous product of incomplete combustion.
Is fluorene biodegradable in water?
If released into water, fluorene is expected to adsorb to suspended solids and sediment based upon the Koc. Using a river die-away test, little or no fluorene was degraded to CO2 over a 24 hr incubation period, suggesting that biodegradation is not an important environmental fate process in water.
What is the fate of fluorene in soil?
TERRESTRIAL FATE: Based on a classification scheme (1), measured log Koc values of 3.70-4.21 (2-4) indicate that fluorene is expected to be immobile in soil (SRC). Volatilization of fluorene from moist soil surfaces is expected to be an important fate process (SRC) given a Henry's Law constant of 9.62X10-5 atm-cu m/mole (5).
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What does fluorene dissolve in?
Soluble in hot ethanol, glacial acetic acid. Soluble in alkalis and ammonia producing a bright green fluorescence.
Is fluorene soluble in ethanol?
(2) The solubility of fluorene increases with the solvents in the order: isopropanol, ethanol, n-butanol, dimethylbenzene, methylbenzene.
Is fluorene soluble in HCL?
It is insoluble in water and soluble in many organic solvents. Although sometimes classified as a polycyclic aromatic hydrocarbon, the five-membered ring has no aromatic properties. Fluorene is mildly acidic....Fluorene.NamesSolubility in water1.992 mg/LSolubilityorganic solventslog P4.18Acidity (pKa)22.634 more rows
Is fluorene soluble in hexane?
bond, but it also has two aromatic rings. Dispersion interactions are strong for such aromatic rings, and the point can be made that this factor will drive the solvation of 9-fluorenone in hexane. This is confirmed by the fact that 9-fluorenone is insoluble in water.
Is fluorene soluble in diethyl ether?
Diethyl ether is the best solvent for dissolving the mixture, because though it is a polar molecule, its ethyl groups make it a nonpolar solvent. The compounds, fluorene and 1, 4-dibromobenzene, are also nonpolar; therefore, it would be easier for it to be dissolved in this organic solvent.
What is a good solvent for fluorene?
Since fluorene is quite nonpolar, a polar solvent is the best bet for crystallization. Since fluorenone is somewhat polar, nonpolar solvents are likely to be good choices for crystallization. Fluorene: Ethanol is a good choice.
Is fluorene soluble in water?
Fluorene or 9H-fluorene is a polycyclic aromatic hydrocarbon insoluble in water and soluble in many organic solvents.
Is fluorene soluble in methanol?
fluorene. Both of them are highly nonpolar, making fluorene highly soluble in toluene. will dissolve. This makes methanol a good solvent.
Is fluorene a polar compound?
Because fluorene is a hydrocarbon and hydrogen and carbon do not have a large difference in their electronegativity values, fluorene is considered non-polar. This means the electrons in the covalent bonds are being shared equally between all of the atoms.
Why is fluorene polar?
Polarity of Fluorene Electronegativity is the ability to attract electrons to the atom in a covalent bond. If there is a significant difference in electronegativity between two or more atoms, we label that molecule as polar because the electrons are not being shared equally.
Is hexane more polar than fluorene?
In principle, the chemical compound that flows through the column at a faster speed is more non-polar; therefore, in this case fluorene was more non-polar than 9-fluorenone....Column Chromatography and TLC.Chemical NameHexaneChemical FormulaC6H14MW: (g/mol)86.18Boiling Point (°C)69Refractive Index (nD)1.3754 more columns•Nov 18, 2013
Why does the fluorene elute first from the column?
The fluorene is eluted first with the hexane, which makes it easier to elute the 9-fluorenone with the dichloromethane. The 9-fluorenone will be slower because it is attracted to the alumina. Stationary phase is non-polar and mobile phase is polar. Most polar is eluted first and least polar is eluted second.
Where does fluorene come from?
Fluorene occurs in fossil fuels. Amounts of up to 1.6% have been reported in coal tar (1). It is released to the atmosphere from the combustion of duff (the thick layer of fermentation and humus matter waste on forest floors) (2).
How is fluorene released?
Its release to the environment is wide spread since it is a ubiquitous product of incomplete combustion. It is released to the atmosphere in emissions from the combustion of oil, gasoline, coal, wood and refuse. Fluorene's production and use in the manufacture of resinous products and dyestuffs may also result in its release to the environment in variosu waste streams. If released to air, a vapor pressure of 6.0X10-4 mm Hg at 25 °C indicates fluorene will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase fluorene will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 1.2 days. Particulate-phase fluorene will be removed from the atmosphere by wet and dry deposition. Fluorene absorbs UV light at wavelengths >290 nm and, therefore, may be susceptible to direct photolysis by sunlight. However, particulate phase fluorene can be stable to photo-oxidation which will permit its long range global transport. If released to soil, fluorene is expected to be immobile based upon a log Koc range of 3.70 to 4.21. Volatilization from moist soil surfaces is expected to be an important fate process based upon a Henry's Law constant of 9.62X10-5 atm-cu m/mole. However, adsorption to soil is expected to attenuate volatilization. Fluorene is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Greater than 92% of initial fluorene was biodegraded using soil contaminated with creosote. No biodegradation occurred using pristine soil suggesting that biodegradation is an important environmental fate process in acclimated soil. If released into water, fluorene is expected to adsorb to suspended solids and sediment based upon the Koc. Using a river die-away test, little or no fluorene was degraded to CO2 over a 24 hr incubation period, suggesting that biodegradation is not an important environmental fate process in water. Volatilization from water surfaces is expected to be an important fate process based upon this compound's Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 15 hrs and 9 days, respectively. However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 190 days if adsorption is considered. Measured log BCF values of 3.02-3.35 suggests bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions (pH 5 to 9). Occupational exposure to fluorene may occur through inhalation and dermal contact with this compound at workplaces where fluorene is inadvertently produced or used. Monitoring data indicate that the general population may be exposed to fluorene via inhalation of ambient air, ingestion of food and drinking water, and smoking cigarettes. (SRC)
What is the Henry's law constant for fluorene?
The Henry's Law constant for fluorene is 9.62X10-5 atm-cu m/mole (1). This Henry's Law constant indicates that fluorene is expected to volatilize from water surfaces (2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) (2) is estimated as 15 hours (SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) (2) is estimated as 9 days (SRC). Fluorene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur (SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 190 days if adsorption is considered (3). Fluorene is not expected to volatilize from dry soil surfaces (SRC) based upon a vapor pressure of 6.0X10-4 mm Hg (4). In a bench-scale biotreatability study, surface volatilization losses of fluorene (solid-phase treatment) and other PAHs amounted to less than 0.01% of total additions (5).
What is the rate constant for the vapor phase reaction of fluorene with photochemically produced hydroxyl
The rate constant for the vapor-phase reaction of fluorene with photochemically-produced hydroxyl radicals is 5.36X10-11 cu cm/molecule-sec at 25 °C (1). This corresponds to an atmospheric half-life of about 1.2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm (2). Aqueous hydrolysis is not an important fate process for fluorene in environmental waters (3,4).
Is fluorene a hydrocarbon?
Fluorescent when impure. (NTP, 1992) CAMEO Chemicals. Fluorene is an ortho-fused tricyclic hydrocarbon that is a major component of fossil fuels and their derivatives It is an ortho-fused polycyclic arene and an ortho-fused tricyclic hydrocarbon.
Not that Fluorine, the Other One
Steven and Alice were asked to write a joint research paper for their organic chemistry class and the assignment was supposed to be centered around a compound called fluorene. They each went their separate ways to research their respective portions of the project. Steven came back very excited to show Alice what he had come up with.
Structure of Fluorene
Let's get started by taking a look at the structure of fluorene. That way we'll know how to recognize it. Fluorene is a polycyclic aromatic hydrocarbon that has three rings covalently bonded together.
Polarity of Fluorene
The term polarity refers to a characteristic of a molecule based on the differences in electronegativity between any of the atoms included in the molecule. Each atom has its own electronegativity value. Electronegativity is the ability to attract electrons to the atom in a covalent bond.
How is fluorene obtained?
Although fluorene is obtained from coal tar , it can also be prepared by dehydrogenation of diphenylmethane. Alternatively, it can be prepared by the reduction of fluorenone with zinc. The fluorene molecule is nearly planar, although each of the two benzene rings is coplanar with the central carbon 9.
What is the precursor to fluorene dye?
Fluorene dyes are well developed. Most are prepared by condensation of the active methylene group with carbonyls. 2-Aminofluorene, 3,6-bis- (dimethylamino)fluorene, and 2,7-diiodofluorene are precursors to dyes.
Is fluorene a hydrocarbon?
It is insoluble in water and soluble in many organic solvents. Although sometimes classified as a polycyclic aromatic hydrocarbon, the five-membered ring has no aromatic properties. Fluorene is mildly acidic.
Is fluorene a precursor to fluorene?
Fluorene is a precursor to other fluorene compounds; the parent species has few applications. Fluorene-9-carboxylic acid is a precursor to pharmaceuticals. Oxidation of fluorene gives fluorenone, which is nitrated to give commercially useful derivatives. 9-Fluorenylmethyl chloroformate (Fmoc chloride) is used to introduce the 9-fluorenylmethyl carbamate (Fmoc) protecting group on amines in peptide synthesis.
What is the fluorene-borylene alternative?
Fluorene–borylene alternative copolymer 90 shows a two-step change of the fluorescence spectra upon addition of cyanide or fluoride ion in THF.48 At the first stage of the anion complexation, a broad and red-shifted emission band develops, which is thought to originate from the charge-transfer excited state between the borate and borane moieties through the conjugated polymer backbone. Further addition of the anions completely quenches the fluorescence emission. A similar fluorescence change is observed in π-conjugated molecules bearing several triarylborane units (e.g., 17, 18, and 19 ).
What is the spiro fluorene dithiolane 129?
The spiro fluorene dithiolane 129 has been prepared and reacted with Fe 3 (CO) 12 to form complexes as models for the active site of a hydrogenase enzyme ( 15CEJ5061 ). The X-ray structure of 130 has been reported and both it and its diselenium analog have been used to form platinum complexes (15POL395 ), while the saturated analog 131 has been reduced by sodium borohydride to furnish the acenaphthene dithiol useful as a transition metal ligand (15JOM (776)7 ). The fluorinated dithiolane 132 is oxidized by mCPBA at low temperature to give the sulfoxide 133 with oxygen cis to the ethoxy group but this is converted upon heating to the more stable trans sulfoxide isomer for which an X-ray structure is reported (15JFC (169)6 ). The parent dithiolane 134 is an effective co-catalyst for FeCl3 -catalyzed chlorination of phenols with sulfuryl chloride ( 15JSC74 ). The dithiolane 135 can be copolymerized with ethyl acrylate to give sulfur-containing polymers (15POC6936), and the water-soluble polymers derived from ring-opening co-polymerization of 136 with polyethylene oxide can be cross-linked to make hydrogels by adding a dithiol ( 15JA5650 ). The new natural product asparaptine 137 has been isolated from asparagus and found to have angiotensin converting enzyme inhibitory activity (15JNP1179) while the antiinflammatory effect of dopamine–lipoic acid hybrid structures 138 has been evaluated ( 15EJP (746)41 ).
Is carbazole an isoelectronic?
Carba zole is isoelectronic with fluorene but the nitrogen bridge improves its hole-accepting abilities (raises the HOMO) and also, unlike the carbon bridge in fluorene, cannot be oxidized to a ketone. As a result poly (2,7-carbazole)s (Figure 22, 53) have been investigated as potentially stable blue emitters, 104,105 whereas the less conjugated poly (3,6-carbazole)s ( 2) have been proposed as hosts for emitters due to their high triplet energies. 15 A problem with 2,7-carbazole-based materials is that, unlike the 3,6-carbazole analogues, they cannot be synthesized directly from carbazole but efficient synthetic routes to 2,7-dihalocarbazole monomers have been developed ( Scheme 7 ). 104,106,107
Is Birch reduction of fluorene selective?
The Birch reduction of fluorene is unselective , with a mixture of regioisomers being formed. In contrast, the Birch reduction of 9.9-bis (trimethylsilyl)fluorene (138) is much more selective, with only the 1,4-dihydro derivative 139 being formed (equation 33). It is suggested that this is a result of the bulky silyl groups directing initial protonation to the 4-position, whereas it appears that in the case of fluorene itself, protonation takes place at both the 2- and 4-positions.96
Is fluorene a hydrocarbon?
Fluorene or 9H -fluorene is a polycyclic aromatic hydrocarbon insoluble in water and soluble in many organic solvents. Fluorenes are one of the most important fluorescent molecules with applications in polymers, electronic devices, sensors, and photochromic materials (Ahmed et al., 2011; Ahmed, 2009; Ahmed and Al-Raqa, 2011) [1–3].
Is fluorene linker compatible with Boc?
1. The fluorene linker is compatible with the Boc strategy and cleaved with piperidine, although cleavage with morpholine afforded slightly purer products. 2. The HMFS handle was prepared in four steps in solution from 2-aminofluorene in 55% overall yield. 3.
What is the structure of fluorenone?
Fluorenone is an aromatic compound that contains a five-membered ring with a carbonyl group attached and two benzene rings fused on either side. Let's break that down a bit.
Is fluorenone soluble or insoluble?
If it does, we say that the compound is soluble. If it doesn't, it is insoluble.
Where is fluorenone found?
Fluorenone is also found in fly ash from municipal incinerators, and in wood smoke and fossil fuel combustion products. If released to the atmosphere, fluorenone will exist in both the vapor and particulate phases in the ambient atmosphere based on an estimated vapor pressure of 5.7X10-5 mm Hg at 25 °C.
How is fluorenone produced?
Fluorenone can be produced by catalytic oxidation of fluorene, or of fluorene fractions in the presence of a quarternary ammonium salt, or by catalytic oxidative cracking (oxicracking) of a suitable aromatic.
What is the Henry's law constant for fluorenone?
The Henry's Law constant for fluorenone is estimated as 6.8X10-7 atm-cu m/mole (SRC) using a fragment constant estimation method (1). This value indicates that fluorenone will volatilize from water surfaces (2,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 73 hours (2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 530 days (2,SRC). Fluorenone's estimated values for vapor pressure, 5.7X10-5 mm Hg (3,SRC), and Henry's Law constant (1,SRC) indicate that volatilization from dry and moist soil will not be a major fate process for this compound (SRC).
How does fluorenone release to the atmosphere?
Fluorenone's production and use as an intermediate or reagent may result in its release to the environment through various waste streams. Fluorenone is also found in fly ash from municipal incinerators, and in wood smoke and fossil fuel combustion products. If released to the atmosphere, fluorenone will exist in both the vapor and particulate phases in the ambient atmosphere based on an estimated vapor pressure of 5.7X10-5 mm Hg at 25 °C. Vapor-phase fluorenone is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 3 days. An estimated Koc of 2300 suggests that fluorenone will have only slight mobility in soil. Volatilization from dry and moist soil surfaces should not be a major fate process for this compound. Based on limited data, this compound may biodegrade in both soil and water. Groundwater, taken from a gasoline contaminated aquifer, was used to inoculate samples containing fluorenone as the sole carbon source; complete degradation was observed by day 11-15. In water, fluorenone is expected to adsorb to sediment and suspended matter based on its Koc value. Fluorenone may volatilize slowly from water surfaces given an estimated Henry's Law constant of 6.8X10-7 atm-cu m/mole. Estimated half-lives for a model river and model lake are 73 and 530 days, respectively. Bioconcentration in aquatic organisms may occur based on an estimated BCF value of 310; fluorenone has been detected in samples of catfish and snails. The general population may be exposed to this compound by ingestion of contaminated drinking water and inhalation of aerosols containing fluorenone. (SRC)
What is the koc of fluorenone?
The Koc of fluorenone is estimated as approximately 2300 (SRC), using a measured log Kow of 3.58 (1) and a regression-derived equation (2,SRC). According to a recommended classification scheme (3), this estimated Koc value suggests that fluorenone has only slight mobility in soil (SRC).
What is phenalen-1-one?
UV spectra were reported along with retention data for gas and liquid chromatography. Mutagenic activity was determined in Salmonella typhimurium, using resistance to the purine analogue 8-azaguanine as a genetic marker. Phenalen-1-one was a potent mutagen, while benzo (c)cinnoline was 6-fold less active. Fluoren-9-one was completely inactive as a bacterial mutagen.
Overview
Fluorene /ˈflʊəriːn/, or 9H-fluorene is an organic compound with the formula (C6H4)2CH2. It forms white crystals that exhibit a characteristic, aromatic odor similar to that of naphthalene. It has a violet fluorescence, hence its name. For commercial purposes it is obtained from coal tar. It is insoluble in water and soluble in many organic solvents. Although sometimes classified as a polycycl…
Synthesis, structure, and reactivity
Although fluorene is obtained from coal tar, it can also be prepared by dehydrogenation of diphenylmethane. Alternatively, it can be prepared by the reduction of fluorenone with zinc or hypophosphorous acid–iodine. The fluorene molecule is nearly planar, although each of the two benzene rings is coplanar with the central carbon 9.
Uses
Fluorene is a precursor to other fluorene compounds; the parent species has few applications. Fluorene-9-carboxylic acid is a precursor to pharmaceuticals. Oxidation of fluorene gives fluorenone, which is nitrated to give commercially useful derivatives. 9-Fluorenylmethyl chloroformate (Fmoc chloride) is used to introduce the 9-fluorenylmethyl carbamate (Fmoc) protecting group on amines in peptide synthesis.
See also
• CataCXium F sulf
• Fluorenol
• Indecainide
• PD-137889
External links
• Fluorene in the National Institute of Standards and Technology database.