fluoranthene
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 1-Adamantanecarboxylic acid In N,N-dimethyl acetamide at 110℃; for 24h; Inert atmosphere; | 98% |
1-(2-fluorophenyl)naphthalene
fluoranthene
Conditions | Yield |
---|---|
With dimethyldimesitylsilane In chlorobenzene at 110℃; for 8h; Friedel Crafts reaction; Inert atmosphere; | 93% |
With aluminum oxide at 150℃; for 60h; Inert atmosphere; | 79% |
1-(2-trifluormethanesulfonyloxyphenyl)naphthalene
fluoranthene
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; lithium chloride; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 140℃; for 6h; | 90% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; lithium chloride; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 140℃; for 6h; other aryl bromides; other MOM phenyl ethers; | 90% |
6b,7,10,10a-tetrahydrofluoranthene-6b,10a-diol
fluoranthene
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 75℃; for 6.5h; | 90% |
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium (0); 1,8-diazabicyclo[5.4.0]undec-7-ene; tricyclohexylphosphine In N,N-dimethyl-formamide at 155℃; for 48h; Suzuki coupling, Heck coupling; | 87% |
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium (0); 1,8-diazabicyclo[5.4.0]undec-7-ene; tricyclohexylphosphine In N,N-dimethyl-formamide at 155℃; for 48h; Suzuki coupling, Heck coupling; | 87% |
3,9-Diethynyl-phenanthrene
A
fluoranthene
B
cyclopenta[c,d]pyrene
C
acephenanthrylene
Conditions | Yield |
---|---|
at 1000℃; under 0.01 Torr; Mechanism; var. of temp.; other polyclic aromatic hydrocarbon with ethynyl subst.; | A 2% B 1% C 4% D 8% E 85% |
Conditions | Yield |
---|---|
at 1000℃; under 0.01 Torr; Further byproducts given; | A 2% B 1% C 8% D 85% |
1-phenyl-2-iodonaphthalene
fluoranthene
Conditions | Yield |
---|---|
With palladium diacetate; cesium pivalate; bis-diphenylphosphinomethane In N,N-dimethyl-formamide at 110℃; for 24h; | 81% |
With palladium diacetate; potassium pivalate; DavePhos In N,N-dimethyl-formamide at 100℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube; | 70% |
With palladium diacetate; cesium pivalate; bis-diphenylphosphinomethane In N,N-dimethyl-formamide at 110℃; for 12h; Inert atmosphere; |
2-(2-bromo-acenaphthylen-yl)-3,6-dihydro-2H-pyran
fluoranthene
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride; palladium diacetate; caesium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 85 - 90℃; for 1.5h; Inert atmosphere; | 80% |
Conditions | Yield |
---|---|
at 120℃; for 3h; Sealed tube; | A 11% B 71% |
1-phenyl-2-bromonaphthalene
fluoranthene
Conditions | Yield |
---|---|
With palladium diacetate; cesium pivalate; bis-diphenylphosphinomethane In N,N-dimethyl-formamide at 110℃; for 72h; | 70% |
fluoranthene
Conditions | Yield |
---|---|
Raney Ni (W2) In ethanol for 6h; Heating; | 70% |
(E)-1-(1-buten-3-ynyl)-8-ethynylnaphthalene
fluoranthene
Conditions | Yield |
---|---|
With hydroquinone In xylene at 150℃; for 6h; Cyclization; | 65% |
2-(naphthalen-1-yl)benzenamine
fluoranthene
Conditions | Yield |
---|---|
With tert.-butylnitrite In acetonitrile at 80℃; for 10h; | 65% |
3H-indazole-3-spiro-1'-naphthalen-4'(1'H)-one
fluoranthene
Conditions | Yield |
---|---|
With water; sodium chloride; zinc | 64% |
Multi-step reaction with 3 steps 1: 94 percent / Heating 2: 66 percent / zinc dust, sodium chloride, water / 3 h / 150 °C / Heating 3: zinc dust, sodium chloride, water / 2 h / 240 °C View Scheme | |
Multi-step reaction with 2 steps 1: 47 percent / 1,2-dichloro-benzene / Heating 2: zinc dust, sodium chloride, water / 2 h / 240 °C View Scheme |
4-phenylnaphtho[2,3-c]furan-1,3-dione
A
1-phenylnaphthalene
B
fluoranthene
C
acephenanthrylene
D
aceanthrylene
Conditions | Yield |
---|---|
1.) 960 deg C, 0.02 mm, 2.) 180-200 deg C, 1.25 h; Yields of byproduct given; | A n/a B 60% C n/a D n/a |
at 960℃; under 0.02 Torr; Mechanism; Product distribution; var. temperature; |
Conditions | Yield |
---|---|
With silver (II) carbonate; triphenyl-arsane; palladium diacetate In 1,2-dichloro-ethane at 80℃; for 18h; Schlenk technique; Inert atmosphere; Sealed tube; | A 20% B 59% |
1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene
1,8-diiodonaphthalene
fluoranthene
Conditions | Yield |
---|---|
With bis(tri-t-butylphosphine)palladium(0); water; caesium carbonate In 1,2-dimethoxyethane at 80℃; for 24h; Suzuki-Miyaura cross-coupling reaction; Inert atmosphere; | 56% |
8-(1-chloroethenyl)fluoranthene
A
fluoranthene
B
benzo[ghi]fluoranthene
Conditions | Yield |
---|---|
at 1200℃; under 0.01 Torr; | A 31% B 17% C 52% |
1,4-dibromonaphthalene
(2-bromophenyl)boronic acid
A
fluoranthene
B
indeno[123-cd]fluoranthene
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium (0); 1,8-diazabicyclo[5.4.0]undec-7-ene; tricyclohexylphosphine In N,N-dimethyl-formamide at 155℃; for 48h; Suzuki coupling, Heck coupling; | A 35% B 51% |
Conditions | Yield |
---|---|
at 1100℃; for 0.000555556h; Product distribution; Mechanism; | A 47% B 14% |
fluoranthene
Conditions | Yield |
---|---|
With sodium hydroxide; tellurium; hydrazine; sodium tetrahydroborate; Aliquat 464 In benzene at 40℃; for 8h; sonication; | 30% |
2-(naphthalen-1-yl)benzenamine
phenylacetylene
A
1-phenylnaphthalene
B
fluoranthene
C
6-phenylbenzo[c]phenanthrene
Conditions | Yield |
---|---|
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tert.-butylnitrite In acetonitrile at 20℃; for 15h; Sealed tube; Irradiation; | A 30% B 20% C 24% |
3,9-Diethynyl-phenanthrene
A
fluoranthene
B
cyclopenta[c,d]pyrene
C
acephenanthrylene
Conditions | Yield |
---|---|
at 1025℃; under 0.01 Torr; Further byproducts given; | A 7% B 8% C 16% D 12% |
3,9-diacetylfluoranthene
A
fluoranthene
B
3-acetylfluoranthene
C
1-(fluoranthen-8-yl)ethanone
Conditions | Yield |
---|---|
With polyphosphoric acid (PPA) at 120℃; Temperature; Inert atmosphere; regioselective reaction; | A n/a B n/a C n/a D 11% |
Triangular [4]phenylene
A
fluoranthene
B
chrysene
C
benzo[ghi]fluoranthene
Conditions | Yield |
---|---|
at 1000℃; flash vacuum pyrolysis; | A 1% B 2.5% C 10% |
Conditions | Yield |
---|---|
With ethyl azidocarbonate In dichloromethane Heating; | 3% |
1-cyclohex-1-enyl-naphthalene
fluoranthene
Conditions | Yield |
---|---|
With chromium corundum at 475 - 530℃; | |
With palladium on activated charcoal at 420 - 455℃; |
Conditions | Yield |
---|---|
With chromium corundum at 475 - 530℃; | |
With palladium on activated charcoal at 420 - 455℃; |
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 0 - 20℃; Friedel-Crafts Acylation; Inert atmosphere; | 100% |
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 5h; Friedel-Crafts Acylation; regioselective reaction; | 42% |
With carbon disulfide; aluminium trichloride |
fluoranthene
2,3-Dihydrofluoranthene
Conditions | Yield |
---|---|
With ammonia; sodium In tetrahydrofuran at -50℃; for 0.416667h; | 100% |
(i) Li, liq. NH3, (ii) NaOMe, MeOH; Multistep reaction; |
Conditions | Yield |
---|---|
With potassium dichromate | 99% |
With potassium dichromate | 99% |
With chromium(VI) oxide; acetic acid for 2h; Heating; | 98% |
fluoranthene
1,2,3,10b-tetrahydrofluoranthene
Conditions | Yield |
---|---|
With tetraethylammonium bromide In ethanol at 60℃; electrolysis, lead cathode; | 98% |
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; methylamine hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; Irradiation; | 96% |
With hydrogenchloride; lithium perchlorate In N,N,N,N,N,N-hexamethylphosphoric triamide Mechanism; electrolysis; presence and absence of ethanol; |
fluoranthene
3-bromofluoranthene
Conditions | Yield |
---|---|
With bromine In nitrobenzene at 20℃; for 20h; | 94% |
With N-Bromosuccinimide In acetonitrile at 20℃; for 24h; | 80% |
With N-Bromosuccinimide In acetonitrile at 20℃; for 18h; | 75% |
fluoranthene
Conditions | Yield |
---|---|
With [mesitylenium]B(C6F5)4; benzene-d6 at 20℃; for 24h; Inert atmosphere; | 93% |
With d7-N,N-dimethylformamide; potassium tert-butylate at 170℃; for 1h; Microwave irradiation; | 75% |
fluoranthene
chromium(0) hexacarbonyl
(1-5,15-η(6)-fluoranthene)(tricarbonyl)chromium
Conditions | Yield |
---|---|
boiling;; | 91% |
boiling;; | 91% |
fluoranthene
Conditions | Yield |
---|---|
In tetrahydrofuran for 2h; | 87% |
Conditions | Yield |
---|---|
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; 1-λ3-benzo[d][1,2]iodaoxol-3(1H)-one In 1,2-dichloro-ethane at 40℃; for 12h; Irradiation; Inert atmosphere; | 87% |
fluoranthene
Conditions | Yield |
---|---|
With iron(III) chloride; nitromethane at 50℃; for 15h; | 84% |
2,4,6-tri(4-pyridyl)-1,3,5-triazine
[Ru2(η6-p-cymene)2(C6H2O4)Cl2]
fluoranthene
silver trifluoromethanesulfonate
Conditions | Yield |
---|---|
In methanol byproducts: AgCl; a mixt. of complex and Ag-salt in methanol was stirred at room temp. for2 h, filtered, triazine-compound and aromatic molecule were added, the mixt. was stirred at room temp. for 24 h; the solvent was removed under vac., the residue was taken up in CH2Cl2, filtered, concd., diethyl ether was added; elem. anal.; | 81% |
2,4,6-tri(4-pyridyl)-1,3,5-triazine
[((hexamethylbenzene)RuCl)2(3,6-dichloro-2,5-dihydroxy-1,4-benzoquinonato(2-))]
fluoranthene
silver trifluoromethanesulfonate
Conditions | Yield |
---|---|
In methanol byproducts: AgCl; a mixt. of complex and Ag-salt in methanol was stirred at room temp. for2 h, filtered, triazine-compound and aromatic molecule were added, the mixt. was stirred at room temp. for 24 h; the solvent was removed under vac., the residue was taken up in CH2Cl2, filtered, concd., diethyl ether was added; elem. anal.; | 77% |
fluoranthene
N-fluorobis(benzenesulfon)imide
Conditions | Yield |
---|---|
With 6,6'-dimethyl-2,2'-bipyridine; copper(I) bromide In 1,2-dichloro-ethane at 70℃; for 12h; Reagent/catalyst; Schlenk technique; Inert atmosphere; regioselective reaction; | 77% |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid; silica gel In dichloromethane at 25℃; for 24h; Nitration; | A 76% B n/a |
With nitric acid; acetic acid |
2,4,6-tri(4-pyridyl)-1,3,5-triazine
Ru2(p-cymene)2(μ4-2,5-dichloro-1,4-benzoquinonato)Cl2
fluoranthene
silver trifluoromethanesulfonate
Conditions | Yield |
---|---|
In methanol byproducts: AgCl; a mixt. of complex and Ag-salt in methanol was stirred at room temp. for2 h, filtered, triazine-compound and aromatic molecule were added, the mixt. was stirred at room temp. for 24 h; the solvent was removed under vac., the residue was taken up in CH2Cl2, filtered, concd., diethyl ether was added; elem. anal.; | 75% |
Conditions | Yield |
---|---|
With o-tetrachloroquinone; silver trifluoromethanesulfonate; palladium diacetate at 50℃; for 14h; Inert atmosphere; regioselective reaction; | 74% |
fluoranthene
A
3-nitrofluoranthene
B
1,2-dinitrofluoranthene
C
1-Nitrofluoranthene
D
2-nitrofluoranthene
E
1,3-dinitrofluoranthene
Conditions | Yield |
---|---|
With dinitrogen tetraoxide; Nitrogen dioxide In tetrachloromethane at 24.5 - 25.5℃; Product distribution; Mechanism; other temperatures, other solvents, other additives; | A 14% B 3% C 1% D 73% E 9% |
fluoranthene
A
3-nitrofluoranthene
B
1,2-dinitrofluoranthene
C
2-nitrofluoranthene
D
1,3-dinitrofluoranthene
Conditions | Yield |
---|---|
With Nitrogen dioxide In tetrachloromethane at 24.5 - 25.5℃; Further byproducts given; | A 14% B 3% C 73% D 9% |
With dinitrogen tetroxide; Nitrogen dioxide; tetrabutylammonium nitrate In tetrachloromethane at 24.5 - 25.5℃; Further byproducts given; | A 14% B 13% C 58% D 14% |
With dinitrogen tetroxide; Nitrogen dioxide; tetrabutylammonium nitrate In tetrachloromethane at 24.5 - 25.5℃; Further byproducts given; | A 12% B 13% C 58% D 17% |
With dinitrogen tetraoxide; Nitrogen dioxide In tetrachloromethane at 25℃; Further byproducts given; | A 23.7 % Chromat. B 12.3 % Chromat. C 53.7 % Chromat. D 7.4 % Chromat. |
Conditions | Yield |
---|---|
With o-tetrachloroquinone; silver trifluoromethanesulfonate; palladium diacetate In 1,2-dichloro-ethane at 80℃; for 2h; Inert atmosphere; regioselective reaction; | 71% |
IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal No Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 32 (1983),p. 355.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
For occupational chemical analysis use NIOSH: Polynuclear Aromatic Hydrocarbons (HPLC), 5506; (GC), 5515.
1. Introduction of Fluoranthene
Fluoranthene, with the CAS No. 206-44-0, has the IUPAC Name of Pentyl nitrite, and it is one kind of light yellow fine crystals. This chemical is insoluble in water, and it belongs to the Product Categories which include Color Former & Related Compounds ; Functional Materials; Sensitizer ; E-LAlphabetic; FA - FLEnvironmental Standards; Alpha Sort; F; PAHs; Volatiles/ Semivolatiles. Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as Fluoranthene, and strong oxidizing agents. They can react exothermically with bases and with diazo compounds.
2. Properties of Fluoranthene
Fluoranthene has the following properties: (1)Melting Point: 109 °C; (2)Flash Point: 8.9 °C; (3)Boiling Point: 105.1 °C at 760 mmHg; (4)Vapour Pressure: 34.9 mmHg at 25°C; (5)Enthalpy of Vaporization: 32.98 kJ/mol; (6)Refractive Index: 1.0996.
3. Structure Descriptors of Fluoranthene
(1). InChI: InChI=1S/C16H10/c1-2-8-13-12(7-1)14-9-3-5-11-6-4-10-15(13)16(11)14/h1-10H
(2). InChIKey: InChIKey=GVEPBJHOBDJJJI-UHFFFAOYSA-N
(3). Smiles: c12c3c4ccccc4c1cccc2ccc3
4. Toxicity of Fluoranthene
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 100mg/kg (100mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00205, | |
rabbit | LD50 | skin | 3180mg/kg (3180mg/kg) | American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962. | |
rat | LD50 | oral | 2gm/kg (2000mg/kg) | American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962. |
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