Phenanthrene

Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) with formula C14H10, consisting of three fused benzene rings. It is a colorless, crystal-like solid, but can also appear yellow. Phenanthrene is used to make dyes, plastics and pesticides, explosives and drugs. It has also been used to make bile acids, cholesterol and steroids.

Phenanthrene
Names
Preferred IUPAC name
Phenanthrene
Identifiers
3D model (JSmol)
1905428
ChEBI
ChemSpider
ECHA InfoCard 100.001.437
EC Number
  • 266-028-2
28699
KEGG
MeSH C031181
UNII
  • 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
  • C1=CC=C2C(=C1)C=CC3=CC=CC=C32
Properties
C14H10
Molar mass 178.234 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)
1.6 mg/L
−127.9·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)
1
1
0
Flash point 171 °C (340 °F; 444 K)
Structure
C2v
0 D
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Phenanthrene occurs naturally and also is a man-made chemical. Commonly, humans are exposed to phenanthrene through inhalation of cigarette smoke, but there are many routes of exposure. Animal studies have shown that phenanthrene is a potential carcinogen. However, according to IARC, it is not identified as a probable, possible or confirmed human carcinogen.

Phenanthrene's three fused rings are angled as in the phenacenes, rather than straight as in the acenes. The compound with a phenanthrene skeleton and nitrogens at the 4 and 5 positions is known as phenanthroline.

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