Phenanthrene

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Phenanthrene
Phenanthrene.png
Phenanthrene-3D-balls.png
Phenanthrene
Identifiers
CAS number 85-01-8 YesY
PubChem 995
ChemSpider 970 N
UNII 448J8E5BST YesY
EC number 266-028-2
KEGG C11422 YesY
MeSH C031181
ChEBI CHEBI:28851 N
Jmol-3D images Image 1
Properties
Molecular formula C14H10
Molar mass 178.23 g mol−1
Appearance Colorless solid
Density 1.18 g/cm3[1]
Melting point 101 °C (214 °F; 374 K)[1]
Boiling point 332 °C (630 °F; 605 K)[1]
Solubility in water 1.6 mg/L[1]
Hazards
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 171 °C (340 °F; 444 K)[1]
Structure
Point group C2v[2]
Dipole moment 0 D
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

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.

Phenanthrene is the backbone of morphinan, which in turn is the backbone of a large number of psychoactive chemicals including antitussives, analgesics, and dissociative drugs.

Chemistry[edit]

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

A classical phenanthrene synthesis is the Bardhan–Sengupta phenanthrene synthesis.[3]

Bardhan–Senguptam phenanthrene synthesis

The first step is an electrophilic aromatic substitution reaction, which is allowed when the diphosphorus 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[edit]

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 occurrences[edit]

Ravatite is a natural mineral consisting of phenanthrene.[9] It is found in small amounts among a few coal burning sites. Ravatite represents a small group of organic minerals.

In February 2014, NASA announced a greatly upgraded database for tracking polycyclic aromatic hydrocarbons (PAHs), including phenanthrene, in the universe. 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 begun forming a couple of billion years after the Big Bang, are widespread throughout the universe, and are associated with new stars and exoplanets.[10]

In plants[edit]

Main article: Phenanthrenes

References[edit]

  1. ^ a b c d e Record of CAS RN 85-01-8 in the GESTIS Substance Database from the IFA
  2. ^ Peter Atkins, J. D. P., Atkins' Physical Chemistry. Oxford: 2010. Pg.443
  3. ^ chempensoftware.com Link
  4. ^ Organic Syntheses, Coll. Vol. 4, p.757 (1963); Vol. 34, p.76 (1954) Link
  5. ^ Organic Syntheses, Coll. Vol. 4, p.313 (1963); Vol. 34, p.31 (1954) Link.
  6. ^ Organic Syntheses, Coll. Vol. 3, p.134 (1955); Vol. 28, p.19 (1948) Link.
  7. ^ Organic Syntheses, Coll. Vol. 2, p.482 (1943); Vol. 16, p.63 (1936) Link.
  8. ^ Organic Syntheses, Coll. Vol. 5, p.489 (1973); Vol. 41, p.41 (1961) Link.
  9. ^ Ravatite Mineral Data
  10. ^ 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. 

External links[edit]