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Acenaphthene

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Name

Acenaphthene

EINECS 201-469-6
CAS No. 83-32-9 Density 1.043 g/cm3
PSA 0.00000 LogP 2.93840
Solubility 0.000347 g/100 mL in water Melting Point 90-94 °C(lit.)
Formula C12H10 Boiling Point 278.999 °C at 760 mmHg
Molecular Weight 154.211 Flash Point 135.257 °C
Transport Information UN 3077 9/PG 3 Appearance white or pale yellow crystalline powder
Safety 26-36/37/39-60-61-37/39-45-36/37-16-7-62-36 Risk Codes 36/37/38-50/53-39/23/24/25-23/24/25-11-52/53-67-65-38
Molecular Structure Molecular Structure of 83-32-9 (Acenaphthene) Hazard Symbols IrritantXi, DangerousN, ToxicT, FlammableF, HarmfulXn
Synonyms

1,8-Ethylenenaphthalene;1,2-Dihydroacenaphthene;

Article Data 129

Acenaphthene Synthetic route

208-96-8

acenaphthylene

83-32-9

acenaphthene

Conditions
ConditionsYield
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%

acenaphthylene

52652-40-1

1,4,4a,9a-tetrahydro-fluorene

A

86-73-7

9H-fluorene

B

83-32-9

acenaphthene

Conditions
ConditionsYield
palladium on activated carbon at 250℃; for 2h;A 93%
B 90%
2025-95-8

1,8-bis(bromomethyl)naphthalene

83-32-9

acenaphthene

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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.
2051-98-1

5-bromoacenaphthene

83-32-9

acenaphthene

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

C

4-Chloro-butyric acid 1-[2H-acenaphthylen-(1Z)-ylidene]-4-chloro-butyl ester

D

2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
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

C

4-Chloro-butyric acid 1-[2H-acenaphthylen-(1E)-ylidene]-4-chloro-butyl ester

D

2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
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%

Acenaphthene Chemical Properties

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 cm
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 Uses

 Acenaphthene (CAS NO.83-32-9) is used in preparation of dyes, pesticides and pharmaceuticals. It does not appear to be carcinogenic.

Acenaphthene 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.

Acenaphthene Consensus Reports

Reported in EPA TSCA Inventory.

Acenaphthene 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  XiIrritant,NDangerous,TToxic,FFlammable,XnHarmful
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

Acenaphthene Analytical Methods

For occupational chemical analysis use NIOSH: Polynuclear Aromatic Hydrocarbons (HPLC), 5506; (GC), 5515.

Acenaphthene 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.

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