PHENANTHRENE

CAS NO:85-01-8
EC NO:266-028-2

Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) with formula C14H10, consisting of three fused benzene rings. 
Phenanthrene is a colorless, crystal-like solid, but can also appear yellow. 
Phenanthrene is used to make dyes, plastics and pesticides, explosives and drugs. Phenanthrene has also been used to make bile acids, cholesterol and steroids.

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. 

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

Properties:
Chemical formula:    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)
Solubility in water:    1.6 mg/L
Magnetic susceptibility (χ):    -127.9·10−6 cm3/mol

Chemistry:
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.

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

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 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
Organic reduction to 9,10-dihydrophenanthrene with hydrogen gas and raney nickel
Electrophilic halogenation to 9-bromophenanthrene with bromine
Aromatic sulfonation to 2 and 3-phenanthrenesulfonic acids with sulfuric acid
Ozonolysis to diphenylaldehyde

Phenanthrene appears as colorless monoclinic crystals with a faint aromatic odor. Solutions exhibit a blue fluorescence. 
Phenanthrene is a polycyclic aromatic hydrocarbon composed of three fused benzene rings which takes its name from the two terms 'phenyl' and 'anthracene.' 
Phenanthrene has a role as an environmental contaminant and a mouse metabolite. 
Phenanthrene is an ortho-fused polycyclic arene, an ortho-fused tricyclic hydrocarbon and a member of phenanthrenes.

Phenanthrene is a natural product found in Buddleja lindleyana, Pterolobium hexapetalum, and Vitis vinifera with data available.

Uses of Phenanthrene:
-Dyestuffs, explosives, synthesis of drugs, biochemical research, manufacturing phenanthrenequinone.
-Phenanthrene forms the basis for production of 9,10-phenanthrenequinone and 2,2'-diphenic acid. 
-Phenanthrene can be used to synthesize anthracene via the isomerization product of sym-octahydrophenanthrene

Industry Uses:
-Adhesives and sealant chemicals

Consumer Uses:
-Adhesives and sealants

Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) derived from coal tar.

Phenanthrene is a polycyclic aromatic hydrocarbon (PAHs) composed of three fused benzene rings which takes its name from the two terms ‘phenyl’ and ‘anthracene. ‘ Phenanthrene has a role as an environmental contaminant and a mouse metabolite.

Most of the Phenanthrenes are used to conduct research. Like most Phenanthrenes, phenanthrene is used to make dyes, plastics and pesticides, explosives and drugs. 
Phenanthrene has also been used to make bile acids, cholesterol and steroids.

Phenanthrene is used in manufacturing dyestuffs and explosives and in biological research. Sources of phenanthrene include diesel fuel exhaust, coal tar pitch and tobacco smoke. 

Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) and has been frequently used as an indicator for monitoring PAH contaminated matrices. 
Phenanthrene induces oxidative stress and inflammation.

About Phenanthrene
Helpful information
Phenanthrene was previously registered under the REACH Regulation but the registration is no longer valid.

Consumer Uses
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which Phenanthrene is most likely to be released to the environment.

Article service life
ECHA has no public registered data on the routes by which Phenanthrene is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.

Widespread uses by professional workers
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the types of manufacture using Phenanthrene. ECHA has no public registered data on the routes by which Phenanthrene is most likely to be released to the environment.

Formulation or re-packing
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which Phenanthrene is most likely to be released to the environment.

Uses at industrial sites
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the types of manufacture using Phenanthrene. ECHA has no public registered data on the routes by which Phenanthrene is most likely to be released to the environment.

Manufacture
ECHA has no public registered data on the routes by which Phenanthrene is most likely to be released to the environment.

Phenanthrene is a polycyclic aromatic hydrocarbon, an environmental pollutant.
Phenanthrene is a polycyclic aromatic hydrocarbon composed of three fused benzene rings.

Phenanthrene is a polycyclic aromatic hydrocarbon (PAH).
Phenanthrene is found in fossil fuels and produced during the combustion of organic material. 
Phenanthrene accumulates in the environment, is toxic to aquatic species, and is considered a pollutant. 
Phenanthrene has been used as an intermediate in the synthesis of certain pesticides, plastics, and steroids.

Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) and has been frequently used as an indicator for monitoring PAH contaminated matrices. 
Phenanthrene induces oxidative stress and inflammation

Chemical & Physical Properties:
Density:    1.1±0.1 g/cm3
Boiling Point:    337.4±9.0 °C at 760 mmHg
Melting Point:    98-100 °C(lit.)
Molecular Formula:    C14H10
Molecular Weight:    178.229
Flash Point:    146.6±12.8 °C
Exact Mass:    178.078247
LogP:    4.68
Vapour Pressure:    0.0±0.3 mmHg at 25°C
Index of Refraction:    1.715
Storage condition:    APPROX 4°C
Stability:    Stable. Combustible. Incompatible with strong oxidizing agents.
Water Solubility:    insoluble

Phenanthrene is a tricyclic aromatic hydrocarbonn (isomeric with anthracene) derived from coal tar melts at 99 C,boils at 340 C, insoluble in water but is soluble in most organic solvents such as toluene, carbon tetrachloride, ether, chloroform, acetic acid and benzene. 
Phenanthrene is a white crystalline substance with a bluish fluorescence. 
Phenanthrene is used in the synthesis of dyes, explosives and drugs. 
Phenanthrene can be used as a feed stock of carbon black.

Phenanthrene is used in the synthesis of dyes, explosives and drugs. 
Phenanthrene can be used as a feed stock of carbon black. 
Phenanthrene is a raw material of phenanthrenequinone which is widely used in the synthesis of dyes, agrochemical and preservatives.

Phenanthrene is the simplest non-linear polycyclic aromatic hydrocarbons with three benzene ring structure, being the isomer of the anthracene. In 1872 E. Ostermayer et al has identified the phenanthrene in the anthracene oil fraction in coal tar distillate, being one of coal tar processing products. In the high-temperature coal tar, the phenanthrene content is secondary only to naphthalene, being about 4~6%, mainly concentrated in the anthracene oil fractions. The chemical activity of phenanthrene is stronger than that of naphthalene, but it is weaker than that of anthracene, and the oxidation and addition reactions can also occur at 9 and 10 positions.

Phenanthren is not soluble in water, slightly soluble in ethanol, soluble in ether, acetic acid, benzene, carbon tetrachloride and carbon disulfide.

Uses    
Phenanthren can be used for the manufacturing of phenanthrenequinone, synthetic resin, pesticides and preservatives and so on.
Phenanthrene, through the oxidation, can give phenanthrenequinone, to be used to replace the organic mercurial pesticides ceresin and gallotox. The biphenyl acid obtained from its oxidation can be used to prepare alkyd resin. 
Phenanthrene oxidation can also give anhydride, cyclohexanone and phenol. The chlorination products of phenanthrene can be used to make non-flammable electrical insulators and impregnants. The sulfonated phenanthrene sulfonic acid can be made of binder, tanning and so on. But in fact most of these applications have yet to be developed. 
In the paper industry, the Phenanthrene can be used as pulp antifogging agent; can also be used for nitroglycerine explosives and nitrocellulose stabilizer and for the manufacture of smoke bomb; the solid oxide of phenanthrene can be made of excellent flame resistant electrical insulating materials and fillers. 
In medicine, phenanthrene can be used for synthesizing alkaloids-morphine and caffeine, dimethyl morphine as well as drugs with special physiological effects on many reproductive organs. 
In the dye industry, the Phenanthrene can be made of 2-aminophenanthrene quinone, benzanthrone, sulfide reduction dye (blue BO, black BB and brown) and so on. 
In addition, the plastic industry, synthetic tanning agents and phenanthrene, under high temperature and high pressure, can undergo hydrogenation to get hydrophenanthrene, being the fuel of senior jet aircraft.
For the determination of molecular weight and the synthesis of organic compounds.

Preparation    
Phenanthrene is a relatively high content of coal tar, accounting for 5% of coal tar, second only to naphthalene content. The anthracene oil in the 300-360 ℃ fraction range of Coal tar has the highest content of Phenanthrene, followed by anthracene and carbazole and so on. 
The phenanthrene extraction method is usually send anthracene oil for cooling, crystallization, and then vacuum filtration or centrifugal separation for oil separation. The relatively high amount of soluble phenols in oils can be recovered using precision distillation method. The obtained crystal is called crude anthracene, which contains 25-30% anthracene, 22-25% carbazole and 30% phenanthrene. Crude anthracene can be subject to heavy benzene extraction, cooling, filtration with the filtrate steamed out of solvent before recrystallization and filtration. Take filtrate for distillation so we can get industrial phenanthrene with sulfonation to get fine phenanthrene.

Description    
Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) 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. 
Phenanthrene appears as a white powder having blue fluorescence.

Chemical Properties    
white crystals

Chemical Properties
Phenanthrene is a white crystalline substance. Weak aromatic odor. Polycyclic aromatic hydrocarbons (PAHs) are compounds containing multiple benzene rings and are also called polynuclear aromatic hydrocarbons.

Physical properties    
Colorless, monoclinic crystals with a faint, aromatic odor

Uses    
Phenanthrene is a polycyclic aromatic hydrocarbons, an environmental pollutant.

Uses    
Labelled polycyclic aromatic hydrocarbons as micropollutants.

Uses    
Phenanthrene is a PAH that can be derived from coal tar. 
Phenanthrene is used in the production of dyes, pharmaceuticals, and explosives, and in biochemical research. A derivative, cyclopentanophenanthrene, has been used as a starting material for synthesizing bile acids, cholesterol, and other steroids.

Production Methods    
Phenanthrene occurs in coal tar and can be isolated from several types of crude petroleum.

Definition    
ChEBI: A polycyclic aromatic hydrocarbon composed of three fused benzene rings which takes its name from the two terms 'phenyl' and 'anthracene.'

Phenanthrene is generally used for dye production, synthetic resin, preservative. Phenanthrene is also used in agrochemical and pharmaceutical intermediates.

IUPAC names:
Phenanthren
Phenanthrene
phenanthrene

SYNONYMS:
1905428 [Beilstein]
200-838-9 [EINECS]
201-581-5 [EINECS]
85-01-8 [RN]
MFCD00001168 [MDL number]
Phenanthren [German] [ACD/IUPAC Name]
Phenanthrene [ACD/Index Name] [ACD/IUPAC Name] [Wiki]
Phénanthrène [French] [ACD/IUPAC Name]
[3]Helicene
1,2,3,4,5,6,7,8,9,10-decadeuteriophenanthrene
104830-06-0 [RN]
1048330-11-5 [RN]
1048970-17-7 [RN]
1173018-81-9 [RN]
1189955-53-0 [RN]
1262770-68-2 [RN]
1517-22-2 [RN]
1985-01-8 [RN]
1-PHENANTHRENYL
201-581-5MFCD00001168
266-028-2 [EINECS]
310-169-5 [EINECS]
4-PHENANTHRENYL
61062-79-1 [RN]
61062-83-7 [RN]
9,10-Dehydrophenanthrene
Decadeuterophenanthrene
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28851
o-Diphenylenethylene