Names | |
---|---|
Preferred IUPAC name Phenanthrene | |
Identifiers | |
3D model (JSmol) | |
1905428 | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.001.437 |
EC Number |
|
28699 | |
KEGG | |
MeSH | C031181 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
| |
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) [1] |
Boiling point | 332 °C (630 °F; 605 K) [1] |
1.6 mg/L [1] | |
−127.9·10−6 cm3/mol | |
Hazards | |
NFPA 704 (fire diamond) | |
Flash point | 171 °C (340 °F; 444 K) [1] |
Structure | |
C2v [2] | |
0 D | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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. [3]
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. [3] However, according to IARC, it is not identified as a probable, possible or confirmed human carcinogen. [4]
Phenanthrene's three fused rings are angled as in the phenacenes, rather than straight as in the acenes. The compounds with a phenanthrene skeleton but with nitrogen atoms in place of CH sites are known as phenanthrolines.
Phenanthrene was discovered in coal tar in 1872 independently by Carl Graebe (article manuscript received on November 1st [5] ) as well as by Wilhelm Rudolph Fittig and his doctoral student Eugen Ostermayer (manuscript received on November 19th [6] but Ostermayer's dissertation defended in August [7] ). Fittig and Ostermayer were able to determine the structure of the compound by oxidizing it first to a corresponding quinone and then to diphenic acid, and soon Graebe confirmed it by a synthesis from stilbene. [8]
Prior to February 1873 Fittig sent a letter to Graebe where he proposed to name the hydrocarbon phenanthrene (German : Phenanthren) in order to account for its similarity to biphenyl and anthracene, which was swiftly adopted. [9]
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.
Phenanthrene is fluorescent under ultraviolet light, exhibiting a large Stoke shift. [10] It can be used in scintillators.
Reactions of phenanthrene typically occur at the 9 and 10 positions, including:
Phenanthrene is extracted from coal tar, where it comprises 5% by weight. [16]
In principle it could be obtained by chemical synthesis. The Bardhan–Sengupta phenanthrene synthesis is a classic way to make phenanthrenes. [17]
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 aromatizes the other rings into aromatic ones as well. The aromatization of six-membered rings produces H2Se.
Phenanthrene can also be obtained photochemically from certain diarylethenes (Mallory reaction):
Other synthesis routes include the Haworth reaction and the Wagner-Meerwein-type ring-expansion, as depicted below:
Commercially phenanthrene is not synthesized but extracted from the byproducts of coal coking, since it makes around 4–6% of coke oven coal tar. [18]
Morphinan is the chemical structure found in several psychoactive drugs, consisting of opiate analgesics, cough suppressants, and dissociative hallucinogens, among others. Examples morphine, codeine, and dextromethorphan (DXM). [16]
Ravatite is a natural mineral consisting of phenanthrene. [19] It is found in small amounts among a few coal burning sites. Ravatite represents a small group of organic minerals.
Phenanthrene derivatives occur in plants as phenanthrenoids. They have been reported from flowering plants, mainly in the family Orchidaceae, and a few in the families Dioscoreaceae, Combretaceae and Betulaceae, as well as in the lower plant class Marchantiophyta (liverworts). [20]
Pyrrole is a heterocyclic, aromatic, organic compound, a five-membered ring with the formula C4H4NH. It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., N-methylpyrrole, C4H4NCH3. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.
Alizarin is an organic compound with formula C
14H
8O
4 that has been used throughout history as a red dye, principally for dyeing textile fabrics. Historically it was derived from the roots of plants of the madder genus. In 1869, it became the first natural dye to be produced synthetically.
The Japp–Klingemann reaction is a chemical reaction used to synthesize hydrazones from β-keto-acids and aryl diazonium salts. The reaction is named after the chemists Francis Robert Japp and Felix Klingemann.
The Bischler–Möhlau indole synthesis, also often referred to as the Bischler indole synthesis, is a chemical reaction that forms a 2-aryl-indole from an α-bromo-acetophenone and excess aniline; it is named after August Bischler and Richard Möhlau .
Friedrich Karl Johannes Thiele was a German chemist and a prominent professor at several universities, including those in Munich and Strasbourg. He developed many laboratory techniques related to isolation of organic compounds. In 1907 he described a device for the accurate determination of melting points, since named Thiele tube after him.
The Reimer–Tiemann reaction is a chemical reaction used for the ortho-formylation of phenols. with the simplest example being the conversion of phenol to salicylaldehyde. The reaction was first reported by Karl Reimer and Ferdinand Tiemann.
The Reissert reaction is a series of chemical reactions that transforms quinoline to quinaldic acid. Quinolines will react with acid chlorides and potassium cyanide to give 1-acyl-2-cyano-1,2-dihydroquinolines, also known as Reissert compounds. Hydrolysis gives the desired quinaldic acid.
1,2,4-Trimethylbenzene, also known as pseudocumene, is an organic compound with the chemical formula C6H3(CH3)3. Classified as an aromatic hydrocarbon, it is a flammable colorless liquid with a strong odor. It is nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar and petroleum (about 3%). It is one of the three isomers of trimethylbenzene.
In chemistry, the cyclopentadienyl anion or cyclopentadienide is an aromatic species with a formula of [C
5H
5]−
and abbreviated as Cp−. It is formed by the deprotonation of cyclopentadiene. The cyclopentadienyl anion is a ligand which binds to a metal in organometallic chemistry.
The Wurtz–Fittig reaction is the chemical reaction of an aryl halide, alkyl halides, and sodium metal to give substituted aromatic compounds. Following the work of Charles Adolphe Wurtz on the sodium-induced coupling of alkyl halides, Wilhelm Rudolph Fittig extended the approach to the coupling of an alkyl halide with an aryl halide. This modification of the Wurtz reaction is considered a separate process and is named for both scientists.
Hans Freiherr von Pechmann was a German chemist, renowned for his discovery of diazomethane in 1894. Pechmann condensation and Pechmann pyrazole synthesis. He also first prepared 1,2-diketones, acetonedicarboxylic acid, methylglyoxal and diphenyltriketone; established the symmetrical structure of anthraquinone.
The Willgerodt rearrangement or Willgerodt reaction is an organic reaction converting an aryl alkyl ketone, alkyne, or alkene to the corresponding amide by reaction with ammonium polysulfide, named after Conrad Willgerodt. The formation of the corresponding carboxylic acid is a side reaction resulting from hydrolysis of the amide. When the alkyl group is an aliphatic chain, multiple reactions take place with the amide group always ending up at the terminal end. The net effect is thus migration of the carbonyl group to the end of the chain and oxidation.
The Schotten–Baumann reaction is a method to synthesize amides from amines and acid chlorides:
Roland Heinrich Scholl was a Swiss chemist who taught at various European universities. Among his most notable achievements are the synthesis of coronene, the co-development of the Bally-Scholl synthesis, and various discoveries about polycyclic aromatic hydrocarbons.
1,2,3-Trimethylbenzene is an organic compound with the chemical formula C6H3(CH3)3. Classified as an aromatic hydrocarbon, it is a flammable colorless liquid. It is nearly insoluble in water but soluble in organic solvents.
2,6-Naphthalenedicarboxylic acid is an organic compound with the formula C10H6(CO2H)2. This colorless solid is one of several isomers of naphthalenedicarboxylic acid. It is a precursor to the high performance polyester polyethylene naphthalate (PEN, poly(ethylene-2,6-naphthalene dicarboxylate)). It is also used in the synthesis of some metal-organic frameworks.
Spiropentane is a hydrocarbon with formula C5H8. It is the simplest spiro-connected cycloalkane, a triangulane. It took several years after the discovery in 1887 until the structure of the molecule was determined. According to the nomenclature rules for spiro compounds, the systematic name is spiro[2.2]pentane. However, there can be no constitutive isomeric spiropentanes, hence the name is unique without brackets and numbers.
Alexander Ellinger was a German chemist and pharmacologist.
Acetyl nitrate is the organic compound with the formula CH3C(O)ONO2. It is classified as the mixed anhydride of nitric and acetic acids. It is a colorless explosive liquid that fumes in moist air.
The Pschorr cyclization is a name reaction in organic chemistry, which was named after its discoverer, the German chemist Robert Pschorr (1868-1930). It describes the intramolecular substitution of aromatic compounds via aryldiazonium salts as intermediates and is catalyzed by copper. The reaction is a variant of the Gomberg-Bachmann reaction. The following reaction scheme shows the Pschorr cyclization for the example of phenanthrene: