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Acenaphthene
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
CAS Number	83-32-9 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:22154 ;
ChEMBL	ChEMBL1797271 ;
ChemSpider	6478 ;
ECHA InfoCard	100.001.336
EC Number	201-469-6;
KEGG	C19312 ;
PubChem CID	6734;
RTECS number	AB1000000;
UNII	V8UT1GAC5Y ;
UN number	3077
CompTox Dashboard (EPA)	DTXSID3021774 ;
	InChI InChI=1S/C12H10/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-6H,7-8H2 Key: CWRYPZZKDGJXCA-UHFFFAOYSA-N ; InChI=1/C12H10/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-6H,7-8H2 Key: CWRYPZZKDGJXCA-UHFFFAOYAW;
	SMILES c2cc1cccc3c1c(c2)CC3; c1cc2cccc3c2c(c1)CC3;
Properties
Chemical formula	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)
Solubility in water	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
Magnetic susceptibility (χ)	-.709·10−6 cm3/g
Thermochemistry
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)	2 1 1
Flash point	135 °C (275 °F; 408 K)
Autoignition; temperature	> 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). verify (what is ?) Infobox references

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]

Production and reactions

Acenaphthene was prepared for the first time in 1866^[4] by Marcellin Berthelot by reacting hot napthalene vapours with acetylene, and a year later he reproduced a similar reaction with ethylene as well as discovered acenaphthene in coal 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 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]⁺.^[6]

Uses

It is used on a large scale to prepare naphthalene dicarboxylic anhydride, which is a precursor to dyes and optical brighteners^[3] (such as 1,4-bis(2-benzoxazolyl)naphthalene). Besides that, the anhydride is also the precursor to perylenetetracarboxylic dianhydride, precursor to several commercial pigments and dyes.^[7]^[8]

References

^ National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina
^ John Rumble (June 18, 2018). CRC Handbook of Chemistry and Physics (99th ed.). CRC Press. pp. 5–3. ISBN 978-1138561632.
^ ^a ^b Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2000). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227. ISBN 3527306730.
^ Annales de chimie et de physique (in French). Chez Crochard. 1866.
^ Annales de chimie et de physique (in French). Masson. 1867.
^ S. B. Kim, S. Lotz, S. Sun, Y. K. Chung, R. D. Pike, D. A. Sweigart "Manganese Tricarbonyl Transfer (MTT) Agents" Inorganic Syntheses, 2010, Vol. 35, 109–128. doi:10.1002/9780470651568.ch6
^ K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a20_371
^ Greene, M. "Perylene Pigments" in High Performance Pigments, 2009, Wiley-VCH, Weinheim. pp. 261-274.doi:10.1002/9783527626915.ch16