Lianyungang Klinechem Co.,Ltd
call us on: +86-518-88103268
English中文
Knowledge
Home > Knowledge > Content

Phenanthrene

Lianyungang Klinechem Co.,Ltd | Updated: Nov 29, 2018

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 smokeand is a known irritantphotosensitizing 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 low polarity organic solvents such as toluenecarbon tetrachlorideetherchloroformacetic acid and benzene.

The Bardhan–Sengupta phenanthrene synthesis is a classic way to make phenanthrenes.[3]

3000

This process involves electrophilic aromatic substitution using a tethered cyclohexanol group using diphosphorus pentoxide, which closes the central ring onto an existing aromatic ring. Dehydrogenationusing selenium converts the other rings into aromatic ones as well. 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:

·        Organic oxidation to phenanthrenequinone with chromic acid[4]

·        Organic reduction to 9,10-dihydrophenanthrene with hydrogen gas and raney nickel[5]

·        Electrophilic halogenation to 9-bromophenanthrene with bromine[6]

·        Aromatic sulfonation to 2 and 3-phenanthrenesulfonic acids with sulfuric acid[7]

·        Ozonolysis to diphenylaldehyde[8]

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 bondsbetween the C4 and C5 hydrogen atoms.

Natural occurrences

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 plants

Main article: Phenanthrenes

See also

·        Chrysene

References[edit]

1.     Jump up to: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.     Jump up^ Peter Atkins, J. D. P., Atkins' Physical Chemistry. Oxford: 2010. Pg.443

3.     Jump up^ "Bardhan Sengupta Synthesis". Comprehensive Organic Name Reactions and Reagents. 49. 2010. pp. 215–219. doi:10.1002/9780470638859.conrr049.

4.     Jump up^ Organic Syntheses, Coll. Vol. 4, p.757 (1963); Vol. 34, p.76 (1954) Link

5.     Jump up^ Organic Syntheses, Coll. Vol. 4, p.313 (1963); Vol. 34, p.31 (1954) Link.

6.     Jump up^ Organic Syntheses, Coll. Vol. 3, p.134 (1955); Vol. 28, p.19 (1948) Link.

7.     Jump up^ Organic Syntheses, Coll. Vol. 2, p.482 (1943); Vol. 16, p.63 (1936) Link.

8.     Jump up^ Organic Syntheses, Coll. Vol. 5, p.489 (1973); Vol. 41, p.41 (1961) Link.

9.     Jump up^ Ravatite Mineral Data


Contact Us
Address: Jingqi Road, Weiwu Road, Coastal Industrial Park, Guanyun County, Lianyungang City, Jiangsu Province
Tel:+86-518-88103268
Fax:+86-518-88103267
E-mail:sales@klinechem.com

© Lianyungang Klinechem Co.,Ltd