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| Names | |
|---|---|
| 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 | |
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3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.001.336 |
| EC Number |
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| KEGG |
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| RTECS number |
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| UNII | |
| UN number | 3077 |
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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 inethanol | slight |
| Solubility inchloroform | slight |
| Solubility inbenzene | very soluble |
| Solubility inacetic acid | soluble |
| Vapor pressure | 0.001 to 0.01 mmHg at 68°F; 5 mmHg at 238.6°F[1] |
| −0.709·10−6 cm3/g | |
| Thermochemistry[2] | |
| 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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Acenaphthene is apolycyclic aromatic hydrocarbon (PAH) consisting ofnaphthalene with anethylene 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 for the first time in 1866[4] byMarcellin Berthelot by reacting hot naphthalene vapours withacetylene, and a year later he reproduced a similar reaction with ethylene as well as discovered acenaphthene incoal tar.[5] Later Berthelot and Bardy synthesized the compound by cyclization of α-ethylnaphthalene. Industrially, it is still obtained from coal tar together with its derivativeacenaphthylene (and many other compounds).
Like otherarenes, acenaphthene forms complexes with low valent metal centers. One example is (η6-acenaphthene)Mn(CO)3]+.[6]
It is used on a large scale to preparenaphthalene dicarboxylic anhydride, which is a precursor to dyes andoptical brighteners[3] (such as 1,4-bis(2-benzoxazolyl)naphthalene). Besides that, the anhydride is also the precursor toperylenetetracarboxylic dianhydride, precursor to several commercialpigments anddyes.[7][8]
