Chrysene

Chrysene^[1]

Names
IUPAC name Chrysene
Other names Benzo[a]phenanthrene 1,2-Benzphenanthrene
Identifiers
CAS Number	218-01-9 Y
ChEBI	CHEBI:51687 Y
ChEMBL	ChEMBL85685 N
ChemSpider	8817 Y
EC Number	205-923-4
Jmol interactive 3D	Image
KEGG	C14222 Y
PubChem	10457109
RTECS number	GC0700000
UNII	084HCM49PT Y
InChI InChI=1S/C18H12/c1-3-7-15-13(5-1)9-11-18-16-8-4-2-6-14(16)10-12-17(15)18/h1-12H Y Key: WDECIBYCCFPHNR-UHFFFAOYSA-N Y InChI=1/C18H12/c1-3-7-15-13(5-1)9-11-18-16-8-4-2-6-14(16)10-12-17(15)18/h1-12H Key: WDECIBYCCFPHNR-UHFFFAOYAK
SMILES c1ccc2c(c1)ccc3c2ccc4c3cccc4
Properties
Chemical formula	C18H12
Molar mass	228.29 g·mol−1
Appearance	Orthorhombic bipyramidal plates
Density	1.274 g/cm3
Melting point	254 °C (489 °F; 527 K)
Boiling point	448 °C (838 °F; 721 K)
Solubility in water	Insoluble
Solubility in ethanol	1 g/1300 mL[2]
Related compounds
Related PAHs	Pyrene, Tetracene, Triphenylene
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

Chrysene is a polycyclic aromatic hydrocarbon (PAH) with the molecular formula C
18H
12 that consists of four fused benzene rings. It is a natural constituent of coal tar, from which it was first isolated and characterized. It is also found in creosote, a chemical used to preserve wood.

The name "chrysene" originates from Greek Χρύσoς (chrysos), meaning "gold", and is due to the golden-yellow color of the crystals of the hydrocarbon, thought to be the proper color of the compound at the time of its isolation and characterization. However, high purity chrysene is colorless, the yellow hue being due to the traces of its yellow-orange isomer tetracene, which cannot be separated easily.

Chrysene is formed in small amounts during the burning or distillation of coal, crude oil, and plant material.

In February 2014, NASA announced a greatly upgraded database for tracking PAHs, including chrysene, in the universe.^[3] According to scientists, more than 20% of the carbon in the universe may be associated with PAHs, possible starting materials for the formation of life. PAHs seem to have been formed shortly after the Big Bang, are widespread throughout the universe, and are associated with new stars and exoplanets.^[4]

Use

Chrysene is used in the manufacture of some dyes.

Safety

As with other PAHs, chrysene is suspected to be a human carcinogen. It is known to cause cancer in laboratory animals.^[5]

Derivatives

Derivatives of chrysene include tetrahydrochrysene and 2,8-dihydroxyhexahydrochrysene, which are estrogenic compounds.

See also

• Phenanthrene

References

1. ↑ Merck Index, 11th Edition, 2259.
2. ↑ Merck Index, 14th edition
3. ↑ NASA Ames PAH IR Spectroscopic Database
4. ↑ Hoover, Rachel (February 21, 2014). "Need to Track Organic Nano-Particles Across the Universe? NASA's Got an App for That". NASA. Retrieved February 22, 2014. 
5. ↑ TOXICOLOGICAL PROFILE FOR POLYCYCLIC AROMATIC HYDROCARBONS