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Basic Information

Molecular Structure:
CAS No.:	83-32-9
Name:	Acenaphthene
Article Data:	129

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

Synthetic route

: 208-96-8
acenaphthylene

: 83-32-9
acenaphthene

Conditions

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%

: acenaphthylene

: 52652-40-1
1,4,4a,9a-tetrahydro-fluorene

A: 86-73-7
9H-fluorene

B: 83-32-9
acenaphthene

Conditions

Conditions	Yield
palladium on activated carbon at 250℃; for 2h;	A 93% B 90%

...Expand

: 2025-95-8
1,8-bis(bromomethyl)naphthalene

: 83-32-9
acenaphthene

Conditions

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

Conditions	Yield
	A n/a B 90%

...Expand

: 2051-98-1
5-bromoacenaphthene

A: 41908-42-3
1,1',2,2'-tetrahydro-5,5'-biacenaphthylene

B: 83-32-9
acenaphthene

Conditions

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.

: 2051-98-1
5-bromoacenaphthene

: 83-32-9
acenaphthene

Conditions

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

Conditions	Yield
With iodine; hypophosphorous acid In acetic acid for 24h; Heating;	A 5% B 40% C 3% D 52%

...Expand

: 2051-98-1
5-bromoacenaphthene

: 201230-82-2
carbon monoxide

A: 55720-22-4
acenaphthene-5-carboxylic acid

B: 83-32-9
acenaphthene

Conditions

Conditions	Yield
With dicobalt octacarbonyl; potassium carbonate; methyloxirane In methanol at 60℃; under 760 Torr; for 6h;	A 50% B n/a

...Expand

: 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

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%

...Expand

: 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

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%

...Expand

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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 Irritant ,N Dangerous ,T Toxic ,F Flammable ,Xn Harmful
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.