Acenaphthene

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Acenaphthene
Skeletal formula Ball-and-stick model
Identifiers
CAS number 83-32-9 YesY
PubChem 6734
ChemSpider 6478 YesY
UNII V8UT1GAC5Y YesY
EC number 201-469-6
UN number 3077
KEGG C19312 N
ChEBI CHEBI:22154 YesY
ChEMBL CHEMBL1797271 N
RTECS number AB1000000
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C12H10
Molar mass 154.21 g mol−1
Appearance White or pale yellow crystalline powder
Density 1.222
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
Hazards
MSDS ICSC 1674
EU Index Not listed
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 135 °C (275 °F; 408 K)
Autoignition temperature >450 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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.[1]

Production and reactions[edit]

Acenaphthene was prepared the first time from coal tar by Marcellin Berthelot. 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]+.[2] Chemical reduction affords the radical anion sodium acenaphthylenide, which is used as a strong reductant (E = 1.75 V vs NHE).[3]

Uses[edit]

It is used on a large scale to prepare naphthalic anhydride, which is a precursor to dyes and optical brighteners.[1]

References[edit]

  1. ^ a b Karl Griesbaum, Arno Behr, Dieter Biedenkapp, Heinz-Werner Voges, Dorothea Garbe, Christian Paetz, Gerd Collin, Dieter Mayer, Hartmut Höke “Hydrocarbons” in Ullmann's Encyclopedia of Industrial Chemistry 2002 Wiley-VCH, Weinheim. doi:10.1002/14356007.a13_227
  2. ^ 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
  3. ^ N. G. Connelly and W. E. Geiger, "Chemical Redox Agents for Organometallic Chemistry", Chem. Rev. 1996, 96, 877-910. doi:10.1021/cr940053x

External links[edit]