Phenanthrene: Difference between revisions

{{short description|Polycyclic aromatic hydrocarbon composed of three fused benzene rings}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 444046459

| ImageFile=Phenanthrene-numbering.svg

| ImageSize=180px

| ImageFile1=Phenanthrene molecule ball.png

| ImageSize1=180px

| ImageAlt1 = Ball-and-stick model of the phenanthrene molecule

| ImageFile2 = Phenanthrene C14H10.JPG

| ImageName2 = Phenanthrene

| PIN = Phenanthrene <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| PubChem=995

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 28851

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 448J8E5BST

| SMILES = C1=CC=C2C(=C1)C=CC3=CC=CC=C32

| EINECS = 266-028-2

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 970

| InChI = 1/C14H10/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-10H

| InChIKey = YNPNZTXNASCQKK-UHFFFAOYAC

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C14H10/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-10H

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = YNPNZTXNASCQKK-UHFFFAOYSA-N

| RTECS =

| MeSHName = C031181

| Beilstein = 1905428

| Gmelin = 28699

|Section2={{Chembox Properties

| C=14 | H=10

| Appearance=Colorless solid

| Density=1.18 g/cm³<ref name=GESTIS/>

| MeltingPtC=101

| MeltingPt_ref = <ref name=GESTIS>{{GESTIS|ZVG=22900|CAS=85-01-8}}</ref>

| BoilingPtC=332

| BoilingPt_ref = <ref name=GESTIS/>

| Solubility=1.6 mg/L<ref name=GESTIS/>

| MagSus = −127.9·10⁻⁶ cm³/mol

|Section3={{Chembox Hazards

| NFPA-H = 1|NFPA-F = 1|NFPA-R=0|NFPA-S =

| MainHazards=

| FlashPtC = 171

| FlashPt_ref = <ref name=GESTIS/>

| AutoignitionPt =

}}

|Section4={{Chembox Structure

| PointGroup = C_2v<ref>Peter Atkins, J. D. P., Atkins' Physical Chemistry. Oxford: 2010. P.&nbsp;443.</ref>

| Dipole = 0 [[Debye|D]]

'''Phenanthrene''' is a [[polycyclic aromatic hydrocarbon]] (PAH) with formula C₁₄H₁₀, consisting of three fused [[benzene]] rings. It is a colorless, crystal-like solid, but can also appear yellow. Phenanthrene is used to make dyes, plastics, pesticides, explosives, and drugs. It has also been used to make bile acids, cholesterol and steroids.<ref name="factsheet">{{cite web |title=Phenanthrene Fact Sheet |url=https://archive.epa.gov/epawaste/hazard/wastemin/web/pdf/phenanth.pdf |website=archive.epa.gov |publisher=U.S. Environmental Protection Agency |access-date=19 July 2019}}</ref>

Phenanthrene occurs naturally and also is a man-made chemical. Commonly, humans are exposed to phenanthrene through inhalation of cigarette smoke, but there are many routes of exposure. Animal studies have shown that phenanthrene is a potential carcinogen.<ref name="factsheet" /> However, according to IARC, it is not identified as a probable, possible or confirmed human carcinogen.<ref>{{cite web |title=Phenanthrene |website=Sigma-Alrdich |url=https://www.sigmaaldrich.com/catalog/product/aldrich/p11409}}</ref>

Phenanthrene's three fused rings are angled as in the [[phenacene]]s, rather than straight as in the [[acene]]s. The compound with a phenanthrene skeleton and nitrogens at the 4 and 5 positions is known as [[phenanthroline]].

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

The '''Bardhan–Sengupta phenanthrene synthesis''' is a classic way to make phenanthrenes.<ref>{{cite book |year= 2010 |chapter= Bardhan Sengupta Synthesis |title= Comprehensive Organic Name Reactions and Reagents |volume= 49 |pages= 215–219 |doi= 10.1002/9780470638859.conrr049 |isbn= 9780470638859 }}</ref>

:[[File:Bardhan-SenguptaPhenanthreneSynthesis.png|480px|Bardhan–Senguptam phenanthrene synthesis]]

This process involves [[electrophilic aromatic substitution]] using a tethered [[cyclohexanol]] group using [[diphosphorus pentoxide]], which closes the central ring onto an existing aromatic ring. [[Dehydrogenation]] using [[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 [[hydrogen selenide|H₂Se]].

* [[Organic oxidation]] to phenanthrenequinone with [[chromic acid]]<ref>[[Organic Syntheses]], Coll. Vol.&nbsp;4, [http://www.orgsynth.org/orgsyn/pdfs/CV4P0757.pdf p.&nbsp;757] (1963); Vol.&nbsp;34, p.&nbsp;76 (1954).</ref>

* [[Organic reduction]] to 9,10-dihydrophenanthrene with [[hydrogen]] gas and [[raney nickel]]<ref>[[Organic Syntheses]], Coll. Vol.&nbsp;4, [http://www.orgsynth.org/orgsyn/pdfs/CV4P0313.pdf p.&nbsp;313] (1963); Vol.&nbsp;34, p.&nbsp;31 (1954).</ref>

* [[Electrophilic halogenation]] to 9-bromophenanthrene with [[bromine]]<ref>[[Organic Syntheses]], Coll. Vol.&nbsp;3, [http://www.orgsynth.org/orgsyn/pdfs/CV3P0134.pdf p.&nbsp;134] (1955); Vol.&nbsp;28, p.&nbsp;19 (1948).</ref>

* [[Aromatic sulfonation]] to 2 and 3-phenanthrenesulfonic acids with [[sulfuric acid]]<ref>[[Organic Syntheses]], Coll. Vol.&nbsp;2, [http://www.orgsynth.org/orgsyn/pdfs/CV2P0482.pdf p.&nbsp;482] (1943); Vol.&nbsp;16, p.&nbsp;63 (1936).</ref>

* [[Ozonolysis]] to diphenylaldehyde<ref>[[Organic Syntheses]], Coll. Vol.&nbsp;5, [http://www.orgsynth.org/orgsyn/pdfs/CV5P0489.pdf p.&nbsp;489] (1973); Vol.&nbsp;41, p.&nbsp;41 (1961).</ref>

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 bond]]s between the C4 and C5 hydrogen atoms.{{cn|date=December 2023}}

== Natural occurrences ==

[[Ravatite]] is a natural mineral consisting of phenanthrene.<ref>[http://webmineral.com/data/Ravatite.shtml Ravatite Mineral Data]</ref> 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 ==

== External links ==

{{Hydrocarbons}}

{{Organic reactions}}

{{Authority control}}

[[Category:Polycyclic aromatic hydrocarbons]]