Phenalene

1H-Phenalene, often called simply phenalene is a polycyclic aromatic hydrocarbon (PAH). Like many PAHs, it is an atmospheric pollutant formed during the combustion of fossil fuels.[2] It is the parent compound for the phosphorus-containing phosphaphenalenes.

Phenalene

Ball-and-stick model of the phenalene molecule
Names
Preferred IUPAC name 1H-Phenalene
Other names 1-Benzonaphthene; 1H-Benzonaphthene; Perinaphthene; Perinaphthindene; peri-Naphthindene
Identifiers
CAS Number	203-80-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:33082
ChemSpider	8795
ECHA InfoCard	100.005.371
PubChem CID	9149
CompTox Dashboard (EPA)	DTXSID5075369
InChI InChI=1S/C13H10/c1-4-10-6-2-8-12-9-3-7-11(5-1)13(10)12/h1-8H,9H2 Key: XDJOIMJURHQYDW-UHFFFAOYSA-N InChI=1/C13H10/c1-4-10-6-2-8-12-9-3-7-11(5-1)13(10)12/h1-8H,9H2 Key: XDJOIMJURHQYDW-UHFFFAOYAK
SMILES c3c1cccc2\C=C/Cc(c12)cc3
Properties
Chemical formula	C13H10
Molar mass	166.22 g/mol
Appearance	white solid
Density	1.139 g/cm^3
Melting point	159–160 °C (318–320 °F; 432–433 K)
Acidity (pKa)	18.1 (in DMSO) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Reactions

Phenalene is deprotonated by potassium methoxide to give the phenalenyl anion.[3]

See also

• Zethrene

References

1. Bausch, M. J.; Guadalupe-fasano, C.; Jirka, G.; Peterson, B.; Selmarten, D. (1991-01-01). "Examinations of Dimethyl Sulfoxide-Phase Equilibrium Acidities of Selected Polycyclic Aromatic Compounds". Polycyclic Aromatic Compounds. 2 (1): 19–27. doi:10.1080/10406639108047854. ISSN 1040-6638.
2. Gao H, Ma MQ, Zhou L, Jia RP, Chen XG, Hu ZD (2007). "Interaction of DNA with aromatic hydrocarbons fraction in atmospheric particulates of Xigu District of Lanzhou, China". J Environ Sci (China). 19 (8): 948–54. doi:10.1016/S1001-0742(07)60156-9. PMID 17966851.
3. Reid, D. H. (1965-01-01). "The chemistry of the phenalenes". Quarterly Reviews, Chemical Society. 19 (3): 274. doi:10.1039/qr9651900274. ISSN 0009-2681.