Anthracene

Anthracene

Names
Preferred IUPAC name Anthracene
Systematic IUPAC name Tricyclo[8.4.0.03,8]tetradeca-1,3,5,7,9,11,13-heptaene
Identifiers
CAS Number	120-12-7 Y
3D model (Jmol)	Interactive image Interactive image
Beilstein Reference	1905429
ChEBI	CHEBI:35298 Y
ChEMBL	ChEMBL333179 Y
ChemSpider	8111 Y
DrugBank	DB07372 Y
ECHA InfoCard	100.003.974
EC Number	217-004-5
Gmelin Reference	67837
KEGG	C14315 Y
PubChem	8418
RTECS number	CA9350000
UNII	EH46A1TLD7 Y
InChI InChI=1S/C14H10/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-10H Y Key: MWPLVEDNUUSJAV-UHFFFAOYSA-N Y InChI=1/C14H10/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-10H Key: MWPLVEDNUUSJAV-UHFFFAOYAK
SMILES c3ccc2cc1ccccc1cc2c3 c1ccc2cc3ccccc3cc2c1
Properties
Chemical formula	C14H10
Molar mass	178.23 g·mol−1
Appearance	Colorless
Odor	Weak aromatic
Density	1.28 g/cm3 (25 °C) 0.969 g/cm3 (220 °C)
Melting point	215.76 °C (420.37 °F; 488.91 K) at 760 mmHg
Boiling point	339.9 °C (643.8 °F; 613.0 K) at 760 mmHg
Solubility in water	0.022 mg/L (0 °C) 0.044 mg/L (25 °C) 0.287 mg/L (50 °C) 0.00045% w/w (100 °C, 3.9 MPa)
Solubility	Soluble in alcohol, (C2H5)2O, acetone, C6H6, CHCl3,CS2
Solubility in ethanol	0.076 g/100 g (16 °C) 1.9 g/100 g (19.5 °C) 0.328 g/100 g (25 °C)
Solubility in methanol	1.8 g/100 g (19.5 °C)
Solubility in hexane	0.37 g/100 g
Solubility in toluene	0.92 g/100 g (16.5 °C) 12.94 g/100 g (100 °C)
Solubility in carbon tetrachloride	0.732 g/100 g
log P	4.56
Vapor pressure	0.01 kPa (125.9 °C) 0.1 kPa (151.5 °C) 13.4 kPa (250 °C)
Henry's law constant (kH)	0.039 L·atm/mol
UV-vis (λmax)	345.6 nm, 363.2 nm
Magnetic susceptibility (χ)	-130·10−6 cm3/mol
Thermal conductivity	0.1416 W/m·K (240 °C) 0.1334 W/m·K (270 °C) 0.1259 W/m·K (300 °C)
Viscosity	0.602 cP (240 °C) 0.498 cP (270 °C) 0.429 cP (300 °C)
Structure
Crystal structure	Monoclinic (290 K)
Space group	P21/b
Point group	C5 2h
Lattice constant	a = 8.562 Å, b = 6.038 Å, c = 11.184 Å α = 90°, β = 124.7°, γ = 90°
Thermochemistry
Specific heat capacity (C)	210.5 J/mol·K
Std molar entropy (So298)	207.5 J/mol·K
Std enthalpy of formation (ΔfHo298)	129.2 kJ/mol
Std enthalpy of combustion (ΔcHo298)	7061 kJ/mol
Hazards
GHS pictograms
GHS signal word	Warning
GHS hazard statements	H315, H319, H335, H410
GHS precautionary statements	P261, P273, P305+351+338, P501
EU classification (DSD)	Xi N
R-phrases	R36/37/38, R50/53
S-phrases	S26, S60, S61
NFPA 704	1 2 1
Flash point	121 °C (250 °F; 394 K)
Autoignition temperature	540 °C (1,004 °F; 813 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	4900 mg/kg (rats, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C₁₄H₁₀, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the production of the red dye alizarin and other dyes. Anthracene is colorless but exhibits a blue (400-500 nm peak) fluorescence under ultraviolet radiation.

Coal tar, which contains around 1.5% anthracene, remains a major source of this material. Common impurities are phenanthrene and carbazole. A classic laboratory method for the preparation of anthracene is by cyclodehydration of o-methyl- or o-methylene-substituted diarylketones in the so-called Elbs reaction.

It may also occur in the interstellar medium. More than 20% of the carbon in the universe may be associated with PAHs, including anthracene.

Anthracene by the action of UV light:

The dimer, called dianthracene (or sometimes paranthracene), is connected by a pair of new carbon-carbon bonds, the result of the [4+4] cycloaddition. It reverts to anthracene thermally or with UV irradiation below 300 nm. Substituted anthracene derivatives behave similarly. The reaction is affected by the presence of oxygen.

Reduction of anthracene with alkali metals yields the deeply colored radical anion salts M⁺[anthracene]⁻ (M = Li, Na, K). Hydrogenation gives 9,10-dihydroanthracene, preserving the aromaticity of the two flanking rings.