85-01-8

Basic information

• Product Name: Phenanthrene
• Synonyms: NSC26256;[3]Helicene;AI3-00790;CCRIS 1233;HSDB 2166;Phenanthren [German];Phenanthrin;Ravatite;UNII-448J8E5BST
• CAS NO: 85-01-8
• Molecular Formula: C14H10
• Molecular Weight: 178.2292
• EINECS: 201-581-5
• Mol File: 85-01-8.mol
• Article Data: 293

Chemical Properties

• Melting Point: 97-101℃
• Boiling Point: 337.355 °C at 760 mmHg
• Flash Point: 146.606 °C
• Appearance: white crystals
• Density: 1.13 g/cm³
• Vapor Pressure: 0.000206mmHg at 25°C
• Refractive Index: 1.714
• Water Solubility: insoluble
• CAS DataBase Reference: Phenanthrene(CAS DataBase Reference)
• NIST Chemistry Reference: Phenanthrene(85-01-8)
• EPA Substance Registry System: Phenanthrene(85-01-8)

Safety Data

• Hazard Codes: Xn:Harmful;;
• Statements: R22:; R40:; R50/53:
• Safety Statements: S29:; S36/37:; S61:
• Hazardous Substances Data: 85-01-8(Hazardous Substances Data)

Usage

Description

Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) consisting of three fused benzene rings. It is a naturally occurring compound found in fossil fuels, coal tar, and crude oil, and can also be produced through the incomplete combustion of organic materials such as wood, tobacco, and petroleum products. Despite its potential carcinogenic and mutagenic properties, which have led to its classification as a priority pollutant by the United States Environmental Protection Agency, phenanthrene has a broad range of industrial applications.

Uses

Used in Chemical Industry:
Phenanthrene is used as a precursor in the production of various chemicals, including dyes, fungicides, and herbicides. Its unique chemical structure allows for the synthesis of a wide range of compounds with diverse applications.
Used in Environmental Monitoring and Mitigation:
Phenanthrene is recognized as an environmental pollutant, and its presence in air, water, and soil is a concern for human health and the environment. As a result, it is used as a target for the development of monitoring and reduction methods to mitigate its impact on the environment and human health.

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

Upstream product

• 128-08-5 N-Bromosuccinimide 
• 1013-08-7 1,2,3,4-tetrahydrophenanthrene 
• 127-08-2 potassium acetate 
• 64-19-7 acetic acid 
• 94-36-0 dibenzoyl peroxide 
• 5325-97-3 1,2,3,4,5,6,7,8-Octahydrophenanthrene 
• 16306-39-1 cis-1,2,3,4,4a,9,10,10a-octahydrophenanthrene 
• 74-85-1 ethene 
• 71-43-2 benzene 
• 5330-97-2 N-hydroxy-2-phenylacetamide 
• 1657-51-8 (Z)-1-chloro-2-styrylbenzene 
• 118-93-4 o-hydroxyacetophenone 
• 61708-79-0 9-mercaptophenanthrene 
• 85704-34-3 1,2-bis(but-1-en-3-ynyl)benzene 

Downstream Products

• 37608-29-0 7,7-dichlorodibenzonorcaradiene 
• 33612-04-3 (1R,2R,2aR,10bS)-1,2-Diphenyl-1,2,2a,10b-tetrahydro-cyclobuta[l]phenanthrene 
• 1217-45-4 9,10-dicyanoanthracene radical anion 
• 84-11-7 9,10-phenanthrenequinone 
• 91-20-3 naphthalene 
• 883-20-5 9-methylphenanthrene 
• 776-35-2 9,10-dihydrophenanthrene 
• 1015-80-1 6,7-dihydro-5H-dibenzo[a,c][7]annulene 
• 219-92-1 dibenzocycloheptene 
• 2510-55-6 9-cyanophenanthrene 
• 56666-55-8 9-(9,10-dihydro)phenanthrenecarbonitrile 
• 585-08-0 phenanthrene-9,10-oxide 
• 92-52-4 biphenyl 
• 80721-78-4 2,6,9,10-tetracyanoanthracene radical anion 

Relevant articles and documents

Photochemistry of supramolecular complex formed by trans-stilbene and the metal-organic coordination polymer

Supramolecular adduct consisting from the metal-organic framework (MOF) [Zn4(dmf)(ur)2(ndc)4] (ndc2- is 2,6-naphtalenedicarboxylate, ur is urotropin, and dmf is N,N'-dimethylformamide) and trans-stilbene was synthesized and its photochemistry was studied. The quantum yield of trans-cis photoisomerization of stilbene in adduct (0.2) was found to be an order of magnitude higher than for crystalline trans-stilbene and comparable with that in organic solvents. The results demonstrate that the creation of MOFs adducts with organic photochroms is a prospective approach for the creation of new hybrid photochromic materials.

Standard enthalpies of formation of phenanthrene and naphthacene

Standard enthalpies of combustion of phenanthrene and naphthacene were determined to be -(7048.7 ± 0.9) kJ·mol-1 and -(9005.1 ± 1.8) kJ·mol-1, respectively, by means of high-precision micro-combustion calorimetry. The former result a

Polycyclic arene episulfides. Attempted synthesis, molecular orbital calculations and comparison with arene oxides

In pursuit of the elusive polycyclic arene episulfides, the synthesis of phenanthrene-9,10-episulfide (5b) was attempted. However, the reactions of phenanthrene-9,10-oxide and of phenanthrene with sulfur transfer agents and of 5,7-dihydrodibenzo[c,e]thiepine (9) with butyllithium did not afford 5b, although its intermediacy could be detected by NMR and inferred from the products isolated. Quantum-mechanical ab initio and density functional methods were used to calculate the thermodynamic stability of representative arene episulfides and arene oxides. The arene episulfides were found to be thermodynamically significantly less stable than the corresponding oxides, towards elimination of sulfur and oxygen respectively. K-region arene episulfides are found to be thermodynamically more stable towards sulfur extrusion than their bay-region isomers. The thermodynamic stabilities of analogous arene oxides and arene episulfides parallel each other, and the relative thermodynamic stabilities of arene oxides and episulfides can be deduced from the degree of the aromatic character of the rings which do not carry the heteroatom.

Synthesis of new furan polycycles via photochemical reaction in neutral and acidic medium

New furan derivatives of o-divinylbenzenes were synthesized and their photochemical reactivity has been investigated in neutral and acidic medium. Depending of the structure of the starting materials and pH value, the new cyclization (11, 16, 20), cycloaddiotion (12, 13, endo-17, exo-18), electrocyclization (21, 22) and dimeric (15, 19) products were isolated. While photochemical investigation in neutral medium showed that the main intramolecular process is cycloaddition, in the case of acidic photochemistry, due to the protonation of the starting molecule, electrocyclization process comes to expression and formation of dihydronaphtalene products 21 and 22.

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Bicyclo[2.2.1]heptan-1-ylcarbene can ring expand

Generation of bicyclo[2.2.1]heptan-1-ylcarbene from a hydrocarbon precursor avoids the problems that attend generation from nitrogenous molecules and allows the determination that such carbenes can ring expand to bridgehead alkenes.

Ni-catalyzed reductive decyanation of nitriles with ethanol as the reductant

A nickel-catalyzed reductive decyanation of aromatic nitriles has been developed, in which the readily available and abundant ethanol was applied as the hydride donor. Various functional groups on the aromatic rings, such as alkoxyl, amino, imino and amide, were compatible in this catalytic protocol. Heteroaryl, benzylic and alkenyl nitriles were also tolerated. Mechanistic investigation indicated that ethanol provided hydride efficientlyviaβ-hydride elimination in this reductive decyanation.

A Bottleable Imidazole-Based Radical as a Single Electron Transfer Reagent

Reduction of 1,3-bis(2,6-diisopropylphenyl)-2,4-diphenyl-1H-imidazol-3-ium chloride (1) resulted in the formation of the first structurally characterized imidazole-based radical 2. 2 was established as a single electron transfer reagent by treating it with an acceptor molecule tetracyanoethylene. Moreover, radical 2 was utilized as an organic electron donor in a number of organic transformations such as in activation of an aryl-halide bond, alkene hydrosilylation, and in catalytic reduction of CO2 to methoxyborane, all under ambient temperature and pressure.