Phenalene

Names

Preferred IUPAC name

1H-Phenalene

Other names

1-Benzonaphthene; 1H-Benzonaphthene; Perinaphthene; Perinaphthindene; peri-Naphthindene

Identifiers

CAS Number

203-80-5^N

3D model (JSmol)

Interactive image

ChEBI

CHEBI:33082^Y

ChemSpider

8795^Y

ECHA InfoCard

100.005.371

PubChem CID

9149

UNII

DQ27KZF2V7^Y

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^Y
Key: XDJOIMJURHQYDW-UHFFFAOYSA-N^Y
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/cm³

Melting point

159–160 °C (318–320 °F; 432–433 K)

Acidity (pK_a)

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).

N verify (what is ^YN ?)

Infobox references

Chemical compound

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.

Reactions

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

References

^ 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.
^ 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.
^ 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.