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| CAS No.: | 83-32-9 |
|---|---|
| Name: | Acenaphthene |
| Molecular Structure: | |
|
|
|
| Formula: | C12H10 |
| Molecular Weight: | 154.211 |
| Synonyms: | 1,8-Ethylenenaphthalene;1,2-Dihydroacenaphthene; |
| EINECS: | 201-469-6 |
| Density: | 1.043 g/cm3 |
| Melting Point: | 90-94 °C(lit.) |
| Boiling Point: | 278.999 °C at 760 mmHg |
| Flash Point: | 135.257 °C |
| Solubility: | 0.000347 g/100 mL in water |
| Appearance: | white or pale yellow crystalline powder |
| Hazard Symbols: |
 Xi,  N,  T,  F,  Xn
|
| Risk Codes: | 36/37/38-50/53-39/23/24/25-23/24/25-11-52/53-67-65-38 |
| Safety: | 26-36/37/39-60-61-37/39-45-36/37-16-7-62-36 |
| Transport Information: | UN 3077 9/PG 3 |
| PSA: | 0.00000 |
| LogP: | 2.93840 |
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| 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 |
- 17057-95-3
1,2,3,4-tetrahydro-9H-fluorene
- 208-96-8
acenaphthylene
A
- 86-73-7
9H-fluorene
B
- 83-32-9
acenaphthene
| Conditions | Yield |
|---|---|
| A n/a B 90% |
- 2051-98-1
5-bromoacenaphthene
A
- 41908-42-3
1,1',2,2'-tetrahydro-5,5'-biacenaphthylene
B
- 83-32-9
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% |
- 108-24-7
acetic anhydride
- 208-96-8
acenaphthylene
A
- 13936-05-5
5-ethylacenaphthene
B
- 7434-96-0
1-acenaphthen-3-yl-ethanone
C
- 10047-18-4
5-acetylacenaphthene
D
- 83-32-9
acenaphthene
| Conditions | Yield |
|---|---|
| With iodine; hypophosphorous acid In acetic acid for 24h; Heating; | A 5% B 40% C 3% D 52% |
- 2051-98-1
5-bromoacenaphthene
- 201230-82-2
carbon monoxide
A
- 55720-22-4
acenaphthene-5-carboxylic acid
B
- 83-32-9
acenaphthene
| Conditions | Yield |
|---|---|
| With dicobalt octacarbonyl; potassium carbonate; methyloxirane In methanol at 60℃; under 760 Torr; for 6h; | A 50% B n/a |
- 20496-01-9
4-chloro-n-butyric anhydride
- 208-96-8
acenaphthylene
A
- 83-32-9
acenaphthene
B
- 88970-55-2
1-Acenaphthen-1-yl-4-chloro-butan-1-one
D
- 2235-15-6
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% |
- 20496-01-9
4-chloro-n-butyric anhydride
- 208-96-8
acenaphthylene
A
- 83-32-9
acenaphthene
B
- 88970-55-2
1-Acenaphthen-1-yl-4-chloro-butan-1-one
D
- 2235-15-6
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% |
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Chemistry
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
Uses
Acenaphthene (CAS NO.83-32-9) is used in preparation of dyes, pesticides and pharmaceuticals. It does not appear to be carcinogenic.
Toxicity Data With Reference
| 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. |
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
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
Analytical Methods
For occupational chemical analysis use NIOSH: Polynuclear Aromatic Hydrocarbons (HPLC), 5506; (GC), 5515.
Specification
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.