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Non-linear polycyclic aromatic hydrocarbons Molecular Structure Chemical properties Uses Preparation

CAS No.85-01-8
Chemical Name:Phenanthrene
Molecular Formula:C14H10
Formula Weight:178.23
MOL File:85-01-8.mol
Phenanthrene Property
Melting point : 98-100 °C(lit.)
Boiling point : 340 °C(lit.)
density : 1.063 g/mL at 25 °C(lit.)
refractive index : 1.5943
Fp : 99-101°C
storage temp. : APPROX 4°C
solubility : Soluble in alcohol, benzene, toluene, and glacial acetic acid
form : platelets (fine)
color : brown
Water Solubility : insoluble
Merck : 14,7212
BRN : 1905428
Stability:: Stable. Combustible. Incompatible with strong oxidizing agents.
CAS DataBase Reference: 85-01-8(CAS DataBase Reference)
NIST Chemistry Reference: Phenanthrene(85-01-8)
EPA Substance Registry System: Phenanthrene(85-01-8)
Hazard Codes : Xn,N,F,T
Risk Statements : 22-36/37/38-50-50/53-40-67-65-38-11-52/53-39/23/24/25-23/24/25-63-43-45-20/21/22-20
Safety Statements : 26-60-61-36/37-29-62-45-16-7-24/25-23-53-37/39-22-33-25-9
RIDADR : UN 3077 9/PG 3
WGK Germany : 2
RTECS : SF7175000
F : 8
TSCA : Yes
HazardClass : 9
PackingGroup : III
Hazardous Substances Data: 85-01-8(Hazardous Substances Data)

Phenanthrene Chemical Properties,Usage,Production

Non-linear polycyclic aromatic hydrocarbons
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.
The phenanthrene is a colorless crystal with luster, and the phenanthrene precipitated from ethanol is a colorless monoclinic crystal. The phenanthrene is a leaf-like crystal with a relative density of 1.179 (25/4 ℃) and a refractive index of 1.6450, melting point of 101 °C and boiling point of 340 °C. It can subject to sublimation, being insoluble in water, slightly soluble in ethanol, soluble in ether, benzene, acetic acid, chloroform, carbon tetrachloride and carbon disulfide. The solution exhibits blue fluorescence. The 1, 4, 5, 8-positions are the same, known as α-position; the 2, 3, 6, 7-position are also the same, known as β-position; the 9, 10-positions are the same, known as the ?-position. Its chemical property is between naphthalene and anthracene. It can also have addition reaction in the 9, 10-position, but not as easy as anthracene. Oxidation also occurs at the 9, 10-position with oxidization giving phenanthrenequinone. Substitution reactions may also occur. It can also be obtained through separation from the anthracene oil fraction of coal tar oil. Phenanthrene can be used in the manufacture of pesticides and dyes, but also be used as the stabilizer of the high efficiency & low toxicity pesticides and smokeless powder explosives.
Phenanthrene can be used to produce dyes, drugs and resins after conversion processing. The oxidation products phenanthrenequinone can be used as dyes, fungicides and polymerization inhibitors; 9, 10-biphenyl dicarboxylic acid is used to manufacture polyester and alkyd resin; 9, 10-dihydro-9-phenathroic acid is a plant growth-stimulating hormone; Perhydrophenanthrene made through hydrogenation of phenanthrene can be used in the production of jet fuel; its sulfonated product, phenanthrene sulfonic acid can be used as binder and tanning.
The phenanthrene-containing mother liquor during the production of refined anthracene using solvent method, after recovery of solvent and further crystallization filtration, can give crude phenanthrene containing 40% phenanthrene.
The crude phenanthrene, after removing of residue solvents in the melting kettle and then rectified in the rectifying tower with 20 theoretical plates, the fractions of 335 to 340 °C are cut out, followed by cooling, crystallization and filtering to obtain the industrial phenanthrene with the phenanthrene content of more than 70%. .
The above information is compiled by Tongtong from Chemicalbook.
Molecular Structure
The molecular structure of phenanthrene and anthracene are similar with each other with all the atoms located in the same plane, but not in the same line, being a closed conjugate system with aromatic property. The 1, 2, 3, 4, 10 positions and 5, 6, 7, 8, 9 positions inside the molecules correspond to each other, respectively, but there were differences in activity at the 5 positions, among which 9 and 10 had higher activity with substitution, oxidation and addition occurring in 9 and 10 positions:
9 and 10 positions

Phenanthrenequinone is a pesticide used as germicide seed dressing, being able to prevent wheat scab, hard smut and sweet potato black spot.
Industrial Phenanthrene is derived from distillation of anthracene oil derived from coal tar distillate. Many kinds of natural products (such as sterols) contain this ring system. Phenanthrene is mainly used in the manufacture of dyes, drugs, high efficiency and low toxicity of pesticides, and can be used as scintillants, smokeless powder stabilizer. Many of the phenanthrene derivatives have carcinogenic physiological effects. Such as:
carcinogenic physiological effects

The molecular structure of 2-methyl-3, 4-benzophenanthrene and 1, 2, 3, 4-dibenzophene

Chemical properties
It appears as white luster and fluorescent flake crystals. It is not soluble in water, slightly soluble in ethanol, soluble in ether, acetic acid, benzene, carbon tetrachloride and carbon disulfide.
It 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.
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.
Chemical Properties
white crystals
Labelled polycyclic aromatic hydrocarbons as micropollutants.
Phenanthrene is a polycyclic aromatic hydrocarbons, an environmental pollutant.
General Description
Colorless monoclinic crystals with a faint aromatic odor. Solutions exhibit a blue fluorescence.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Phenanthrene may react with oxidizing materials .
Fire Hazard
Phenanthrene is combustible.
Phenanthrene Preparation Products And Raw materials
Raw materials
heavy benzol COAL TAR Carbazole COAL TAR Anthracene
Preparation Products
Cyclohexane Ziegler catalyst、Phillips catalyst Phenanthrenequinone HALOFANTRINE Diphenic acid Benzene Anthracene phanquone 9-Bromophenanthrene
Phenanthrene Suppliers      Global( 173)Suppliers     
Tianjin Zhongxin Chemtech Co., Ltd. 86(0)22-8988073986(0)22-89880739 ext 8030 / 86-22-66880086sales@tjzxchem.comChina 553 60
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Chemvon Biotechnology Co., Ltd +86-21-50790412+86-21-50790419marketing@chemvon.comChina 313 57
Meryer (Shanghai) Chemical Technology Co., Ltd. +86-(0)21-61259100(Shanghai) +86-(0)755-86170099(ShenZhen) +86-(0)10-59487313(Beijing)+86-(0)21-61259102(Shanghai) +86-(0)755-86170066(ShenZhen) +86-(0)10-88580358(Beijing)sh@meryer.comChina 40403 62
Alfa Aesar 400-610-6006; 021-67582000021-67582001/03/05saleschina@alfa-asia.comChina 30315 84
TCI (Shanghai) Development Co., Ltd. 22833 81
BeiJing Hwrk Chemicals Limted 4006990298;010-57411839;0757-86311057;021-51691807010-87653215;0757-86311057;021-55236763sales@hwrkchemical.comChina 16340 55
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