1-bromo-1H,3H-naphtho<1,8-cd>thiopyran 2,2-dioxide
acenaphthylene
Conditions | Yield |
---|---|
With sodium methylate In methanol for 16.5h; Ambient temperature; | 97% |
With sodium methylate In methanol for 16.5h; Product distribution; Ambient temperature; var. of base; | 97% |
acenaphthene
7,7',8,8'-tetracyanoquinodimethane
A
9-Acenaphthyl<4-(dicyanomethyl)phenyl>dicyanomethane
B
acenaphthylene
Conditions | Yield |
---|---|
for 0.0833333h; Heating; | A 95.5% B n/a |
Carbonic acid acenaphthen-1-yl ester methyl ester
acenaphthylene
Conditions | Yield |
---|---|
With 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 60℃; for 48h; | 95% |
Propynoic acid acenaphthen-1-yl ester
acenaphthylene
Conditions | Yield |
---|---|
at 760℃; under 0.03 Torr; | 95% |
Multi-step reaction with 2 steps 1: 32 percent / deuterium oxide, triethylamine / tetrahydrofuran / 1.25 h / 35 °C 2: 95 percent / 760 °C / 0.03 Torr View Scheme |
acenaphthylene
Conditions | Yield |
---|---|
at 760℃; under 0.03 Torr; | 95% |
trans-1,2-dibromo-1,2-dihydroacenaphthylene
acenaphthylene
Conditions | Yield |
---|---|
With acetic acid; zinc | 94% |
With ethanol; zinc |
1,2-dibromoacenaphthene
acenaphthylene
Conditions | Yield |
---|---|
With sodium sulfide; Aliquat 336 In water; benzene for 1h; Ambient temperature; | 92% |
Conditions | Yield |
---|---|
methyltrioxorhenium(VII) In benzene for 72h; | 89% |
zirconium(IV) chloride In acetonitrile at 20℃; for 0.666667h; | 89% |
With pyridine; thionyl chloride |
Conditions | Yield |
---|---|
at 500℃; under 0.02 Torr; for 0.0833333h; | A 88% B 4% |
Conditions | Yield |
---|---|
at 800℃; under 0.1 Torr; Cyclization; Pyrolysis; | A 81% B 2% |
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 24h; Reflux; | 80% |
With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite In toluene at 120℃; under 9750.98 Torr; for 8h; | 77% |
With manganese(IV) oxide In benzene for 30h; Heating; | 41% |
Conditions | Yield |
---|---|
With Lawessons reagent In toluene for 0.5h; Heating; | A 72% B 13% |
With Lawessons reagent In toluene for 0.5h; Heating; | A 72% B 13% |
acenaphthene
chloranil
A
2,3,5,6-tetrachlorobenzene-1,4-diol
B
acenaphthylene
Conditions | Yield |
---|---|
In benzene for 18h; Irradiation; | A 68% B 19% |
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; iodine In tetrahydrofuran Kinetics; to a soln. of nucleophile in THF was added soln. of complex in THF at -60°C; after 45 min at -60°C I2 in THF was added and soln. allowed to stir overnight while being warmed to room temp.;; soln. was filtered through Celite, evapd., extd. with ether, extract was washed with other solvents, then chromd. on silica column, eluent CHCl3-hexane;; | A 19% B 20% C 68% |
acenaphthylene
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 24h; Schlenk technique; Inert atmosphere; Reflux; | 57% |
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; iodine; trifluoroacetic acid In tetrahydrofuran to a soln. of nucleophile in THF at -60°C soln. of complex was added, after 45 min at -60°C CF3COOH was added followed by I2, and soln. was allowed to stir overnight while being warmed to room temp.;; soln. was filtered through Celite, evapd.; residue was extd. was ether and washed with other solvents; then chromd. on silica column, eluent CH2Cl2-hexane;; | A 47% B 8% |
Conditions | Yield |
---|---|
at 780℃; under 1 Torr; for 0.0833333h; | A 43% B 19% C 37% |
dichloromethane
(naphthalene-1,8-diyl)dilithium
A
naphthalene
B
1,1'-cis-ethene-1,2-diyl-bis-naphthalene
C
(E)-1,2-bis(1-naphthyl)ethene
D
1H-Cyclobutanaphthalene
E
1-Chloromethylnaphthalene
F
acenaphthylene
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine In diethyl ether at -100 - -60℃; Product distribution; Mechanism; var. of temp., further with CD2Cl2; | A 42% B n/a C n/a D 21% E n/a F n/a |
dichloromethane
(naphthalene-1,8-diyl)dilithium
A
naphthalene
B
1,1'-cis-ethene-1,2-diyl-bis-naphthalene
C
1H-Cyclobutanaphthalene
D
acenaphthylene
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine In diethyl ether at -100 - -60℃; Further byproducts given; | A 42% B n/a C 21% D n/a |
(acenaphthylene)chromium tricarbonyl
A
C40H44N2O2
B
C20H23NO
C
acenaphthylene
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; iodine In tetrahydrofuran to a soln. of nucleophile in THF at -60°C soln. of complex was added, after 45 min at -60°C soln. of I2 in THF was added, and soln. was allowed to stir overnight while being warmed to room temp.;; soln. was filtered through Celite, evapd.; residue was extd. was ether and washed with other solvents; then chromd. on silica column, eluent CH2Cl2-hexane;; | A 16% B 42% C 41% |
2-(2-ethynyl-phenyl)-thiophene
A
naphtho[1,2-b]thiophene
B
acenaphthylene
Conditions | Yield |
---|---|
at 1000℃; under 0.1 Torr; Cyclization; rearrangement; Pyrolysis; | A 18% B 41% |
acenaphthene quinone
A
1-acenaphthenol
B
acenaphthene
C
acenaphthylene
Conditions | Yield |
---|---|
With samarium diiodide; water In tetrahydrofuran at 20℃; for 0.00277778h; | A 41% B 26% C 23% |
A
acenaphthene
B
9-Hydroxymethyl-1H-naphtho[1,2-c]furan-3-one
C
acenaphthylene
Conditions | Yield |
---|---|
at 730℃; under 0.03 Torr; for 0.05h; | A 9% B 38% C 12% |
1,3-dibromo-1H,3H-naphtho<1,8-cd>thiopyran 2,2-dioxide
A
decacyclene
B
1-bromoacenaphthylene
C
acenaphthylene
Conditions | Yield |
---|---|
With potassium tert-butylate In tert-butyl alcohol at 27℃; for 18h; Product distribution; other reagents; | A 5% B 33% C 23% |
With potassium tert-butylate In tert-butyl alcohol for 1.5h; Heating; | A 5% B n/a C n/a |
acenaphthene quinone
A
decacyclene
B
1-acenaphthenol
C
acenaphthene
D
acenaphthylene
Conditions | Yield |
---|---|
bis(η6-biphenyl)titanium(0) In toluene at 110℃; for 2h; Further byproducts given; | A 21% B 10% C 11% D 31% |
acenaphthene quinone
A
decacyclene
B
trans-biacenaphthylidene
C
cis-biacenaphthylidene
D
acenaphthylene
Conditions | Yield |
---|---|
bis(η6-biphenyl)titanium(0) In toluene at 110℃; for 2h; Yield given. Further byproducts given; | A 21% B n/a C n/a D 31% |
1,2-dihydroacenaphthylen-1-yl diazoacetate
acenaphthylene
Conditions | Yield |
---|---|
at 340℃; under 0.02 Torr; | 22% |
acenaphthylene
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 24h; Schlenk technique; Inert atmosphere; Reflux; | 21% |
(acenaphthylene)chromium tricarbonyl
lithium isobutyronitrile
A
C16H13N
B
acenaphthylene
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; iodine; trifluoroacetic acid In tetrahydrofuran to a soln. of nucleophile in THF at -60°C soln. of complex was added, after 45 min at -60°C CF3COOH was added followed by I2, and soln. was allowed to stir overnight while being warmed to room temp.;; soln. was filtered through Celite, evapd.; residue was extd. was ether and washed with other solvents; then chromd. on silica column, eluent CH2Cl2-hexane;; | A 20% B 3% |
Conditions | Yield |
---|---|
With tetraethylammonium bromide In ethanol at 60℃; electrolysis, lead cathode; | 100% |
With benzenetellurol In ethanol; ethyl acetate for 4h; Product distribution; Heating; other reagent, reaction time; | 98% |
With iodine; hypophosphorous acid In acetic acid for 24h; Heating; | 98% |
Conditions | Yield |
---|---|
In acetic acid | 100% |
acenaphthylene
acenaphthylene
Conditions | Yield |
---|---|
With 6-per-deoxy-6-per-(2-sulfoethyl)thio-γ-cyclodextrin, sodium salt for 12h; UV-irradiation; stereoselective reaction; | 100% |
With Rosebengal In methanol Irradiation; | 65% |
In hexane at 25℃; Irradiation; | |
With racemic palladium-ruthenium heterometallic cage with 3-{1H-imidazo[4,5-f]1,10-phenanthrolin-2-yl}pyridine In water; dimethyl sulfoxide at 20℃; Kinetics; Catalytic behavior; Reagent/catalyst; Solvent; Irradiation; |
acenaphthylene
7,8,9,10-Tetrachloro-6b,10a-dihydro-fluoranthene
Conditions | Yield |
---|---|
at 20℃; for 1h; | 100% |
acenaphthylene
trans-1,2-dibromo-1,2-dihydroacenaphthylene
Conditions | Yield |
---|---|
With tri(decyl)(methyl)phosphonium tribromide In Hexadecane for 240h; | 100% |
With hydrogen bromide; oxygen; sodium nitrite In water; acetonitrile at 22℃; for 8h; diastereoselective reaction; | 96% |
With pyridinium hydrobromide perbromide In tetrahydrofuran at -78 - 20℃; | 93% |
Conditions | Yield |
---|---|
Stage #1: methanol; 4-allylguaiacol With [bis(acetoxy)iodo]benzene; sodium hydrogencarbonate In benzene at 0℃; for 0.166667h; Stage #2: acenaphthylene In benzene at 20℃; for 22h; Diels-Alder reaction; stereoselective reaction; | 100% |
1,3-diphenyl-2H-cyclopenta<1>phenanthren-2-one
acenaphthylene
C40H26
Conditions | Yield |
---|---|
In xylene Reflux; | 100% |
Conditions | Yield |
---|---|
In diethyl ether; dichloromethane; o-xylene at 100 - 140℃; for 2h; | 100% |
acenaphthylene
6b,7a-dihydroacenaphtho [1,2-b]oxirene
Conditions | Yield |
---|---|
Stage #1: acenaphthylene With N-Bromosuccinimide In water; dimethyl sulfoxide at 20℃; for 2h; Stage #2: With sodium hydroxide In diethyl ether at 20℃; | 99% |
With 3,3-dimethyldioxirane In acetone at 20℃; for 1h; | 97% |
With 2-Nitrobenzenesulfonyl chloride In acetonitrile at -30℃; for 10h; Product distribution; various arenes, solvents + times; | 95% |
Conditions | Yield |
---|---|
With 5,5’-bis(diphenylphosphino)-2,2,2’,2’-tetrafluoro-4,4’-bi-1,3-benzodioxole; [Rh(OH)(cod)]2 In 1,4-dioxane at 60℃; for 6h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With oxygen; isobutyraldehyde In acetonitrile at 60℃; for 3h; | 98% |
With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) In fluorobenzene at 100℃; under 7500.6 Torr; | 87% |
With iodosylbenzene; iron(III) tetraphenylporphyrin In dichloromethane for 1h; | 58% |
With iodosylbenzene; μ-oxo dimer of iron(III)porphyrinate In methanol at 21.9℃; for 3h; Product distribution; Mechanism; catalysts also Fe(III)porphyrinate, Fe(III)tetraphenylporphyrinate; protic and aprotic solvents; inhibition effect by phenanthrene; by-products; | 28% |
With dinitrogen monoxide at 300℃; under 367754 Torr; |
Conditions | Yield |
---|---|
In diethyl ether at 0℃; | 98% |
N-ethoxycarbonyl-(2,3,4,5-tetrachloro-1-thiophenio)amide
acenaphthylene
(6bS,10aR)-7,8,9,10-Tetrachloro-6b,10a-dihydro-fluoranthene
Conditions | Yield |
---|---|
at 20℃; for 0.166667h; | 98% |
Conditions | Yield |
---|---|
With 5,5’-bis(diphenylphosphino)-2,2,2’,2’-tetrafluoro-4,4’-bi-1,3-benzodioxole; [Rh(OH)(cod)]2 In 1,4-dioxane at 60℃; for 6h; Inert atmosphere; Schlenk technique; enantioselective reaction; | 98% |
Conditions | Yield |
---|---|
In acetic acid | 97% |
Conditions | Yield |
---|---|
With 5,5’-bis(diphenylphosphino)-2,2,2’,2’-tetrafluoro-4,4’-bi-1,3-benzodioxole; tert-Amyl alcohol; [Rh(OH)(cod)]2 In 1,4-dioxane at 60℃; for 6h; Inert atmosphere; Schlenk technique; enantioselective reaction; | 97% |
N-(ethoxycarbonyl)-(2,3,4,5-tetrachloro-1-thiophenio)amide S-oxide
acenaphthylene
A
sulfinylcarbamic acid ethyl ester
B
(6bS,10aR)-7,8,9,10-Tetrachloro-6b,10a-dihydro-fluoranthene
Conditions | Yield |
---|---|
In dichloromethane for 1h; | A 89% B 96% |
Conditions | Yield |
---|---|
In acetic acid | 96% |
acenaphthylene
Conditions | Yield |
---|---|
With pyridine In chloroform at 70℃; for 24h; | 96% |
Conditions | Yield |
---|---|
With Br2Co*C27H26P2; zinc(II) iodide; zinc In dichloromethane at 25℃; for 48h; | 95% |
bis(pinacol)diborane
acenaphthylene
2-(1,2-dihydroacenaphthylen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With methanol; (2-mesityl-5-methyl-2,3-dihydroimidazo[1,5-a]pyridin-3-yl)copper(I) chloride; sodium t-butanolate In diethyl ether at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; | 95% |
1,3-diphenylisobenzofuran
acenaphthylene
10.13-Diphenyl-10.13-endoxy-11:12-benzo-9.10.13.14-tetrahydrofluoranthen
Conditions | Yield |
---|---|
In 5,5-dimethyl-1,3-cyclohexadiene Reflux; | 94.85% |
In benzonitrile at 140℃; for 7h; | 60% |
Conditions | Yield |
---|---|
With Raney Ni-Al In potassium hydroxide; water at 90℃; for 6.5h; Reduction; | 94% |
With hydrogen; nickel at 250℃; |
Conditions | Yield |
---|---|
With benzeneseleninic anhydride In chlorobenzene at 120℃; for 2h; | 94% |
With N-Bromosuccinimide; water; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 60 - 70℃; for 3h; | 79% |
With sodium dichromate; cerous nitrate In acetic acid for 19h; Ambient temperature; | 36% |
1. Introduction of Acenaphthalene
The IUPAC name of this chemical is Acenaphthylene. With the CAS registry number 208-96-8 and EINECS 205-917-1, it is also named as Cyclopenta(de)naphthalene. In addition, the molecular formula is C12H8 and the molecular weight is 152.20. It is a kind of yellow crystalline powder and insoluble in water. What's more, it belongs to the class of Industrial/Fine Chemicals; AA to ALAnalytical Standards; A; A-BAlphabetic; Alpha Sort; AromaticsChemical Class; Chemical Class; Hydrocarbons; NeatsAnalytical Standards; PAHs; Volatiles/ Semivolatiles; Arenes; Building Blocks; Organic Building Blocks; Naphthalenes; AA to AL; Alphabetic.
2. Physical properties about this chemical
(1)ACD/LogP: 3.27; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.266; (4)ACD/LogD (pH 7.4): 3.266; (5)ACD/BCF (pH 5.5): 178.758; (6)ACD/BCF (pH 7.4): 178.758; (7)ACD/KOC (pH 5.5): 1424.886; (8)ACD/KOC (pH 7.4): 1424.886; (9)Index of Refraction: 1.732; (10)Molar Refractivity: 51.262 cm3; (11)Molar Volume: 128.196 cm3; (12)Polarizability: 20.322 ×10-24cm3; (13)Surface Tension: 54.72 dyne/cm; (14)Density: 1.187 g/cm3; (15)Flash Point: 137.161 °C; (16)Enthalpy of Vaporization: 51.726 kJ/mol; (17)Boiling Point: 298.86 °C at 760 mmHg; (18)Vapour Pressure: 0.002 mmHg at 25°C.
3.Structure descriptors of Acenaphthalene
(1)SMILES: c1cc2cccc3c2c(c1)C=C3
(2)InChI: InChI=1/C12H8/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-8H
(3)InChIKey: HXGDTGSAIMULJN-UHFFFAOYAQ
4. Preparation of Acenaphthylene
Acenaphthalene can be prepared by acenaphthene through vapor-phase catalytic dehydrogenation. Put industrial acenaphthene into molten kettle, use an indirect steam heat it to melt, then use compressed air press acenaphthene liquid into the spiral mixer gasification. After heating the mixture to about 450 °C, let the mixture into dehydrogenation reactor for catalytic dehydrogenation, condense and dry the product.
5.Uses of Acenaphthylene
Acenaphthalene can be used for determinating aryl aldehyde. And it can be used to get 1,2-dichloro-acenaphthene. This reaction will need reagents iodosobenzene and HCl-silica gel and solvent solid. The reaction time is 5 minutes at ambient temperature. The yield is about 31%.
6.Safety information of Acenaphthalene
This chemical is highly flammable, harmful if swallowed and irritating to eyes, respiratory system and skin. It may cause lung damage if swallowed and may cause drowsiness and dizziness. In addition, it is very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. And it has danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. During using it, avoid release to the environment and wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). This material and its container must be disposed of as hazardous waste. And you should refer to special instructions/safety data sheets. If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. Keep away from sources of ignition and keep container tightly closed at last.
7.The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | 1760mg/kg (1760mg/kg) | AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BLOOD: HEMORRHAGE | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 9(9), Pg. 53, 1965. |
rat | LD50 | intraperitoneal | 1700mg/kg (1700mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 14(6), Pg. 46, 1970. |
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