Phenanthrene

Phenanthrene

Names
Preferred IUPAC name Phenanthrene
Other names Tricyclo[8.4.0.02,7]tetradeca-1,3,5,7,9,11,13-heptaene
Identifiers
CAS Number	85-01-8 Y
3D model (Jmol)	Interactive image
Beilstein Reference	1905428
ChEBI	CHEBI:28851 N
ChemSpider	970 N
ECHA InfoCard	100.001.437
EC Number	266-028-2
Gmelin Reference	28699
KEGG	C11422 Y
MeSH	C031181
PubChem	995
UNII	448J8E5BST Y
InChI InChI=1S/C14H10/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-10H N Key: YNPNZTXNASCQKK-UHFFFAOYSA-N N InChI=1/C14H10/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-10H Key: YNPNZTXNASCQKK-UHFFFAOYAC
SMILES c1ccc2c3ccccc3ccc2c1
Properties
Chemical formula	C14H10
Molar mass	178.23 g·mol−1
Appearance	Colorless solid
Density	1.18 g/cm3
Melting point	101 °C (214 °F; 374 K)
Boiling point	332 °C (630 °F; 605 K)
Solubility in water	1.6 mg/L
Magnetic susceptibility (χ)	-127.9·10−6 cm3/mol
Hazards
NFPA 704	1 1 0
Flash point	171 °C (340 °F; 444 K)
Structure
Point group	C2v
Dipole moment	0 D
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

Phenanthrene is a polycyclic aromatic hydrocarbon composed of three fused benzene rings. The name 'phenanthrene' is a composite of phenyl and anthracene. In its pure form, it is found in cigarette smoke and is a known irritant, photosensitizing skin to light. Phenanthrene appears as a white powder having blue fluorescence.

The compound with a phenanthrene skeleton and nitrogens at the 4 and 5 positions is known as phenanthroline.

Phenanthrene is nearly insoluble in water but is soluble in most low polarity organic solvents such as toluene, carbon tetrachloride, ether, chloroform, acetic acid and benzene.

The Bardhan–Sengupta phenanthrene synthesis is a classic way to make phenanthrenes.

This process involves electrophilic aromatic substitution using a tethered cyclohexanol group using diphosphorus pentoxide, which closes the central ring onto an existing aromatic ring. Dehydrogenation using selenium converts the other rings into aromatic ones as well. The aromatization of six-membered rings by selenium is not clearly understood, but it does produce H₂Se.

Phenanthrene can also be obtained photochemically from certain diarylethenes.

Reactions of phenanthrene typically occur at the 9 and 10 positions, including:

Phenanthrene is more stable than its linear isomer anthracene. A classic and well established explanation is based on Clar's rule. A novel theory invokes so-called stabilizing hydrogen-hydrogen bonds between the C4 and C5 hydrogen atoms.