Names | |
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Preferred IUPAC name
1,2-Dihydroacenaphthylene | |
Other names
1,8-Ethylenenaphthalene
peri-Ethylenenaphthalene Naphthyleneethylene Tricyclo[6.3.1.04,12]dodecapentaene Tricyclo[6.3.1.04,12]dodeca-1(12),4,6,8,10-pentaene | |
Identifiers | |
3D model (
JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.001.336 |
EC Number |
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KEGG | |
PubChem
CID
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RTECS number |
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UNII | |
UN number | 3077 |
CompTox Dashboard (
EPA)
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Properties | |
C12H10 | |
Molar mass | 154.212 g·mol−1 |
Appearance | White or pale yellow crystalline powder |
Density | 1.024 g/cm3 |
Melting point | 93.4 °C (200.1 °F; 366.5 K) |
Boiling point | 279 °C (534 °F; 552 K) |
0.4 mg/100 ml | |
Solubility in ethanol | slight |
Solubility in chloroform | slight |
Solubility in benzene | very soluble |
Solubility in acetic acid | soluble |
Vapor pressure | 0.001 to 0.01 mmHg at 68°F ; 5 mmHg at 238.6°F [1] |
-.709·10−6 cm3/g | |
Thermochemistry [2] | |
Heat capacity (C)
|
190.4 J mol−1 K−1 |
Std molar
entropy (S⦵298) |
188.9 J mol−1 K−1 |
Std enthalpy of
formation (ΔfH⦵298) |
70.3 kJ/mol |
Hazards | |
NFPA 704 (fire diamond) | |
Flash point | 135 °C (275 °F; 408 K) |
> 450 °C (842 °F; 723 K) | |
Safety data sheet (SDS) | ICSC 1674 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Acenaphthene is a polycyclic aromatic hydrocarbon (PAH) consisting of naphthalene with an ethylene bridge connecting positions 1 and 8. It is a colourless solid. Coal tar consists of about 0.3% of this compound. [3]
Acenaphthene was prepared the first time from coal tar by Marcellin Berthelot. [4] Later Berthelot and Bardy synthesized the compound by cyclization of α-ethylnaphthalene. Industrially, it is still obtained from coal tar together with its derivative acenaphthylene (and many other compounds).
Like other arenes, acenaphthene forms complexes with low valent metal centers. One example is (η6-acenaphthene)Mn(CO)3+. [5]
It is used on a large scale to prepare naphthalene dicarboxylic anhydride, which is a precursor to dyes and optical brighteners. [3] Naphthalene dicarboxylic anhydride is the precursor to perylenetetracarboxylic dianhydride, precursor to several commercial pigments and dyes. [6] [7]
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