Jump to content

Phenanthrene

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by 98.114.189.211 (talk) at 22:54, 20 May 2012 (→‎Natural occurrence: reference added). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Phenanthrene
Names
IUPAC name
Phenanthrene
Identifiers
3D model (JSmol)
ECHA InfoCard 100.001.437 Edit this at Wikidata
KEGG
UNII
  • InChI=1/C14H10/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-10H
  • c1ccc2c(c1)ccc3ccccc32
Properties
C14H10
Molar mass 178.234 g·mol−1
Appearance Colorless solid
Density 1.18 g/cm3[1]
Melting point 101 °C (214 °F; 374 K)
Boiling point 332 °C (630 °F; 605 K)
1.6 mg/L[1]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point 171 °C (340 °F)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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.[citation needed] 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.

Chemistry

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

A classical phenanthrene synthesis is the Bardhan-Sengupta phenanthrene synthesis.[2]

Bardhan-Senguptam phenanthrene synthesis

The first step is an electrophilic aromatic substitution reaction, which is allowed when the diphosphorous pentoxide makes the alcohol a better leaving group. However, no alkenes outside of the initial aromatic ring are created. In the second step of this reaction 9,10-dihydrophenanthrene is oxidized with elemental selenium. 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:

Canonical forms

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.

Natural occurrence

Ravatite is a natural mineral consisting of phenanthrene.[8] It is found in small amounts among a few coal burning sites. Ravatite represents a small group of organic minerals.

References

  1. ^ a b c d e Record of CAS RN 85-01-8 in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ chempensoftware.com Link
  3. ^ Organic Syntheses, Coll. Vol. 4, p.757 (1963); Vol. 34, p.76 (1954) Link
  4. ^ Organic Syntheses, Coll. Vol. 4, p.313 (1963); Vol. 34, p.31 (1954) Link.
  5. ^ Organic Syntheses, Coll. Vol. 3, p.134 (1955); Vol. 28, p.19 (1948) Link.
  6. ^ Organic Syntheses, Coll. Vol. 2, p.482 (1943); Vol. 16, p.63 (1936) Link.
  7. ^ Organic Syntheses, Coll. Vol. 5, p.489 (1973); Vol. 41, p.41 (1961) Link.
  8. ^ Ravatite Mineral Data

External links

Retrieved from "https://en.wikipedia.org/w/index.php?title=Phenanthrene&oldid=493575093"