Acenaphthene

Acenaphthene

Names
IUPAC name 1,2-Dihydroacenaphthylene
Systematic IUPAC name Tricyclo[6.3.1.04,12]dodeca-1(12),4,6,8,10-pentaene
Other names 1,8-Ethylenenaphthalene peri-Ethylenenaphthalene Naphthyleneethylene Tricyclo[6.3.1.04,12]dodecapentaene
Identifiers
CAS Number	83-32-9 Y
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:22154 Y
ChEMBL	ChEMBL1797271 N
ChemSpider	6478 Y
ECHA InfoCard	100.001.336
EC Number	201-469-6
KEGG	C19312 N
PubChem	6734
RTECS number	AB1000000
UNII	V8UT1GAC5Y Y
UN number	3077
InChI InChI=1S/C12H10/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-6H,7-8H2 Y Key: CWRYPZZKDGJXCA-UHFFFAOYSA-N Y 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	154.21 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
Magnetic susceptibility (χ)	-.709·10−6 cm3/g
Hazards
Safety data sheet	ICSC 1674
NFPA 704	1 2 1
Flash point	135 °C (275 °F; 408 K)
Autoignition temperature	> 450 °C (842 °F; 723 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
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.

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]⁺. Chemical reduction affords the radical anion sodium acenaphthylenide, which is used as a strong reductant (E = -1.75 V vs NHE).

It is used on a large scale to prepare naphthalene dicarboxylic anhydride, which is a precursor to dyes and optical brighteners. Naphthalene dicarboxylic anhydride is the precursor to perylenetetracarboxylic dianhydride, precursor to several commercial pigments and dyes.