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 |
---|---|
palladium on activated carbon at 250℃; for 2h; | A 93% B 90% |
Conditions | Yield |
---|---|
With hexamethyldistannane; palladium In toluene at 110℃; for 18h; | 90% |
With norborn-2-ene; benzophenone In acetonitrile Irradiation; | 8.1% |
With phenyllithium; benzene |
1,2,3,4-tetrahydro-9H-fluorene
acenaphthylene
A
9H-fluorene
B
acenaphthene
Conditions | Yield |
---|---|
A n/a B 90% |
5-bromoacenaphthene
A
1,1',2,2'-tetrahydro-5,5'-biacenaphthylene
B
acenaphthene
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl-formamide at 70℃; for 3h; Dimerization; dehalogenation; | A 85% B 5% |
With 9,10-phenanthroline; nickel dichloride; zinc In N,N-dimethyl-formamide at 70℃; for 3h; Dehalogenation; dimerization; | A 71% B 15% |
Stage #1: 5-bromoacenaphthene With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl-formamide at 70℃; for 6h; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide at 30 - 40℃; for 0.5h; Title compound not separated from byproducts; | A 95 % Chromat. B 5 % Chromat. |
Conditions | Yield |
---|---|
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 2h; | 81% |
acetic anhydride
acenaphthylene
A
5-ethylacenaphthene
B
1-acenaphthen-3-yl-ethanone
C
5-acetylacenaphthene
D
acenaphthene
Conditions | Yield |
---|---|
With iodine; hypophosphorous acid In acetic acid for 24h; Heating; | A 5% B 40% C 3% D 52% |
5-bromoacenaphthene
carbon monoxide
A
acenaphthene-5-carboxylic acid
B
acenaphthene
Conditions | Yield |
---|---|
With dicobalt octacarbonyl; potassium carbonate; methyloxirane In methanol at 60℃; under 760 Torr; for 6h; | A 50% B n/a |
4-chloro-n-butyric anhydride
acenaphthylene
A
acenaphthene
B
1-Acenaphthen-1-yl-4-chloro-butan-1-one
D
1(2H)-acenaphthylenone
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide electrolysis at -1.7 V (0.1 M TBAI); Further byproducts given; | A 6% B 46% C n/a D 8.5% |
In N,N-dimethyl-formamide electrolysis at -1.7 V (0.1 M TBAI); Further byproducts given; | A 6% B 46% C 8.5% D 8.5% |
4-chloro-n-butyric anhydride
acenaphthylene
A
acenaphthene
B
1-Acenaphthen-1-yl-4-chloro-butan-1-one
D
1(2H)-acenaphthylenone
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide electrolysis at -1.7 V (0.1 M TBAI); Further byproducts given; | A 6% B 46% C 3.5% D 8.5% |
acetic anhydride
acenaphthylene
A
acenaphthene
D
1(2H)-acenaphthylenone
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide electrolysis at -1.7 V (0.1 M TBAI); Further byproducts given; | A 9% B 43% C 18% D n/a |
Conditions | Yield |
---|---|
at 780℃; under 1 Torr; for 0.0833333h; | A 43% B 19% C 37% |
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% |
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% |
carbon dioxide
acenaphthylene
methyl iodide
A
acenaphthene
trans-1,2-dicarbomethoxy-1,2-dihydroacenaphthylene
D
1(2H)-acenaphthylenone
Conditions | Yield |
---|---|
1.) electrolysis at -1.7 V (0.1 M TBAI), DMF, -35 deg C; 2) overnight; Yield given. Multistep reaction. Further byproducts given; | A 9% B n/a C 18% D n/a |
acenaphthene
Conditions | Yield |
---|---|
With benzophenone In acetonitrile Irradiation; | 12.3% |
In cyclohexane Irradiation; with a KrF (248 nm) excimer laser; | |
In cyclohexane Irradiation; |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide electrolysis at -1.7 V (0.1 M TBAI); Further byproducts given; | A 9% B 3% C 4% D 11% |
1,8-bis(phenylthiomethyl)-naphthalene
acenaphthene
Conditions | Yield |
---|---|
With benzophenone In acetonitrile Irradiation; | 5.5% |
In cyclohexane Irradiation; with a KrF (248 nm) excimer laser; | 72 % Spectr. |
In cyclohexane Irradiation; |
n-butyl magnesium bromide
phosgene
diethyl ether
3-bromoacenaphthene
acenaphthene
Conditions | Yield |
---|---|
bei Rotglut; |
naphthalene
ethene
A
2,2'-binaphthalene
B
phenanthrene
C
acenaphthene
Conditions | Yield |
---|---|
beim Leiten durch ein gluehendes Rohr; |
Conditions | Yield |
---|---|
With sulfur at 180℃; |
cis-acenaphthene-1,2-diol
(+/-)-(2aξH)-2a.3.4.5-tetrahydro-acenaphthenediol-(1r.2c)
B
acenaphthene
Conditions | Yield |
---|---|
With hydrogenchloride; ethanol; iron(III) chloride at 50℃; Hydrogenation.weiteres Reagens: Platin; |
Conditions | Yield |
---|---|
With acetic acid; zinc |
Conditions | Yield |
---|---|
With palladium on activated charcoal |
Conditions | Yield |
---|---|
With palladium on activated charcoal |
(8-carboxy-[1]naphthyl)-glyoxylic acid
acenaphthene
Conditions | Yield |
---|---|
With phosphorus; hydrogen iodide |
acenaphthene-1,5-dicarboxylic acid
A
acenaphthene-5-carboxylic acid
B
acenaphthene
Conditions | Yield |
---|---|
at 280℃; |
Conditions | Yield |
---|---|
at 200℃; im Rohr; |
Conditions | Yield |
---|---|
100% | |
aluminum nickel | 100% |
Rh/C | 100% |
acenaphthene
9,9,10,10-tetradeuteroacenaphthene tetradeuteroacenaphthene
Conditions | Yield |
---|---|
With dimethylsulfoxide-d6; sodium hydride at 78℃; for 22h; | 100% |
With sodium dimsylate-d5; dimethylsulfoxide-d6 at 75℃; for 20h; | |
With water-d2; sodium hydride In dimethylsulfoxide-d6 | 99.8 %Spectr. |
With dimethylsulfoxide-d6; sodium hydride |
Conditions | Yield |
---|---|
With oxygen at 300 - 330℃; | 100% |
With oxygen at 300 - 330℃; | 100% |
With oxygen at 300 - 330℃; | 100% |
acenaphthene
Conditions | Yield |
---|---|
With hydrogen; palladium 10% on activated carbon at 130℃; under 3000.3 - 7500.75 Torr; for 4 - 10h; Product distribution / selectivity; | 99.5% |
Conditions | Yield |
---|---|
With cerium(III) chloride heptahydrate; dihydrogen peroxide; acetic acid; sodium bromide In water at 20℃; for 3h; Reagent/catalyst; Temperature; | 97.5% |
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 3h; | 97% |
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; | 96% |
chloro-trimethyl-silane
acenaphthene
4,5,7,8-tetrakis(trimethylsilyl)-4,5,7,8-tetrahydroacenaphthene
Conditions | Yield |
---|---|
With lithium In tetrahydrofuran at 0 - 5℃; | 97% |
Conditions | Yield |
---|---|
With Iron(III) nitrate nonahydrate; acetic acid at 35℃; for 5h; Reagent/catalyst; Temperature; | 96% |
With bismuth(III) nitrate; acetic anhydride; acetic acid at 20℃; for 6h; Reagent/catalyst; Temperature; | 96.5% |
With nitric acid In dichloromethane at 10℃; for 1.33333h; | 90% |
Conditions | Yield |
---|---|
With hydrogen In n-heptane at 150 - 200℃; under 15001.5 Torr; for 1h; Autoclave; | 96.2% |
With Raney Ni-Al In potassium hydroxide; water at 90℃; for 6.5h; Reduction; | 93% |
With cobalt(II) chloride hexahydrate; lithium In tetrahydrofuran at 25℃; for 2h; Birch reaction; Inert atmosphere; regioselective reaction; | 88% |
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 |
chloral hydrate
acenaphthene
1,1,1-trichloro-2,2-di(acenaphth-4-yl)ethane
Conditions | Yield |
---|---|
With sulfuric acid In chloroform 1.) 20 deg C, 1 h, 2.) 25 deg C, 3 h; | 94% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; for 3h; | 93.6% |
Conditions | Yield |
---|---|
With sodium dichromate | 92% |
With copper(II) acetate dihydrate; manganese(II) acetate dihydrate; oxygen; acetic acid; potassium bromide at 105℃; | 90% |
With sodium dichromate In acetic acid at 75℃; for 8h; | 80% |
2,2-bis(4-chlorocarbonylphenyl)-hexafluoropropane
acenaphthene
(4-{1-[4-(Acenaphthene-5-carbonyl)-phenyl]-2,2,2-trifluoro-1-trifluoromethyl-ethyl}-phenyl)-acenaphthen-5-yl-methanone
Conditions | Yield |
---|---|
With aluminium trichloride In 1,2-dichloro-ethane 1.) 0 -> 60 deg C, 2 h, 2.) 60 deg C, 1 h; | 92% |
1,2,4,5-tetracyanobenzene
acenaphthene
A
5-(acenapthen-1-yl)benzene-1,2,4-tricarbonitrile
B
4,6-di(acenaphthen-1-yl)benzene-1,3-dicarbonitrile
C
acenaphthene quinone
Conditions | Yield |
---|---|
In acetonitrile for 12h; Product distribution; Mechanism; Irradiation; other solvents, irradiation at different wave-length; | A 90% B 1.5% C n/a |
In acetonitrile for 12h; Irradiation; | A 90% B 1.5% C 2 mg |
acenaphthene
trifluoromethanesulphonyloxy-methylene-N,N-dimethyliminium trifluoromethanesulphonate
acenaphthene-5-carbaldehyde
Conditions | Yield |
---|---|
In chloroform at 130℃; for 72h; | 90% |
1,8-bis(2,6-dichlorophenylethynyl)naphthalene
acenaphthene
7,14-bis(2,6-dichlorophenyl)acenaphtho[1,2-k]fluoranthene
Conditions | Yield |
---|---|
Stage #1: 1,8-bis(2,6-dichlorophenylethynyl)naphthalene; acenaphthene With tris(triphenylphosphine)rhodium(l) chloride In 5,5-dimethyl-1,3-cyclohexadiene at 110℃; for 60h; Inert atmosphere; Sealed tube; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 5,5-dimethyl-1,3-cyclohexadiene at 20 - 110℃; Inert atmosphere; Sealed tube; | 90% |
acenaphthene
N,N-dimethyl-formamide
1,2-dihydroacenaphthylene-3-carbaldehyde
Conditions | Yield |
---|---|
With silica gel; trichlorophosphate for 0.025h; Formylation; Microwave irradiation (300 W); | 89% |
Conditions | Yield |
---|---|
With aluminum (III) chloride In 1,1,2,2-tetrachloroethane at 20℃; | 87% |
With carbon disulfide; aluminium trichloride |
acenaphthene
N,N-dimethyl-formamide
acenaphthene-5-carbaldehyde
Conditions | Yield |
---|---|
With trichlorophosphate at 90 - 95℃; for 3h; Vilsmeier Reaction; | 85% |
With trichlorophosphate at 70℃; for 3h; | 57% |
With trichlorophosphate at 90 - 95℃; for 3.33h; | 46.74% |
acenaphthene
1,2-dibromoacenaphthylene
Conditions | Yield |
---|---|
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 4h; Inert atmosphere; Reflux; | 84% |
With N-Bromosuccinimide; benzoic acid anhydride | |
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 2h; Reflux; | |
With N-Bromosuccinimide |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; V2O5/TiO2 In water at 80℃; for 8h; Sealed tube; Green chemistry; | 82% |
With potassium permanganate; sulfuric acid; triethylamine In chloroform Ambient temperature; | 76% |
With tetrakis(pyridine)silver(II) peroxodisulfate In acetonitrile for 1h; Heating; | 60% |
Conditions | Yield |
---|---|
With benzeneseleninic anhydride In chlorobenzene at 120℃; for 24h; | 81% |
With sodium dichromate; acetic acid ; cerium (IV)-acetate; acetic acid at 40℃; Reagens 4: CeCl3; | |
With ammonium dichromate; acetic acid at 100℃; |
Conditions | Yield |
---|---|
With tin(IV) chloride at 140℃; | 80% |
With tin(IV) chloride |
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% |
Product Name: Acenaphthene (CAS NO.83-32-9)
IUPAC Name: 1,2-dihydroacenaphthylene
Molecular formula: C12H10
Formula weight: 154.21
Index of Refraction: 1.691
Molar Refractivity: 51.65 cm3
Molar Volume: 134.9 cm3
Surface Tension: 49.2 dyne/cm
Density: 1.143 g/cm3
Flash Point: 135.3 °C
Enthalpy of Vaporization: 49.68 kJ/mol
Boiling Point: 279 °C at 760 mmHg
Vapour Pressure: 0.00698 mmHg at 25°C
Product Categories: Aromatic Compounds; Aromatic Hydrocarbons (substituted) & Derivatives; Highly Purified Reagents; Other Categories; Zone Refined Products; A; AA to ALAnalytical Standards; A-BAlphabetic; Alpha Sort; Chemical Class; Naphthalenes; Volatiles/ Semivolatiles; AromaticsChemical Class; Hydrocarbons; NeatsAnalytical Standards; PAHs
Acenaphthene (CAS NO.83-32-9) is used in preparation of dyes, pesticides and pharmaceuticals. It does not appear to be carcinogenic.
1. | mmo-omi 3 mg | MIKBA5 Mikrobiologiya. 54 (1985),360. | ||
2. | ipr-rat LD50:600 mg/kg | GTPZAB Gigiena Truda i Professional’nye Zabolevaniia. Labor Hygiene and Occupational Diseases. 14 (6)(1970),46. |
Reported in EPA TSCA Inventory.
Moderately toxic by intraperitoneal route. Mutation data reported.Incompatible with strong oxidizing agents, ozone, chlorinating agents. When heated to decomposition it emits acrid smoke and irritating vapors.
For occupational chemical analysis use NIOSH: Polynuclear Aromatic Hydrocarbons (HPLC), 5506; (GC), 5515.
Hazard Codes Xi,N,T,F,Xn
Risk Statements 36/37/38-50/53-39/23/24/25-23/24/25-11-52/53-67-65-38
R36/37/38:Irritating to eyes, respiratory system and skin.
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.
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R67:Vapours may cause drowsiness and dizziness. R65:Harmful: may cause lung damage if swallowed.
R38:Irritating to skin.
Safety Statements 26-36/37/39-60-61-37/39-45-36/37-16-7-62-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
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.
S37/39:Wear suitable gloves and eye/face protection.
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.
S17:Keep away from combustible material.
S62:If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label.
S36:Wear suitable protective clothing.
RIDADR UN 3077 9/PG 3
WGK Germany 3
RTECS AB1000000
HazardClass 9
PackingGroup III
HS Code 29029080
For occupational chemical analysis use NIOSH: Polynuclear Aromatic Hydrocarbons (HPLC), 5506; (GC), 5515.
Acenaphthene (CAS NO.83-32-9) is a polycyclic aromatic hydrocarbon (PAH) consisting of naphthalene with an ethylene bridge connecting positions 1 and 8. An alternative name, 1,2-dihydroacenaphthylene, emphasizes that it is a hydrogenated form of acenaphthylene. It is a constituent of coal tar. It was prepared the first time from coal tar by Marcellin Berthelot and after that with Bardy he synthesized it from α-ethyl naphthalene.
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