Pyrene

Base Information

• Chemical Name: Pyrene
• CAS No.: 129-00-0
• Deprecated CAS: 76165-23-6
• Molecular Formula: C16H10
• Molecular Weight: 202.255
• Hs Code.: 29349990
• European Community (EC) Number: 204-927-3
• ICSC Number: 1474
• NSC Number: 66449,17534
• UN Number: 3082
• UNII: 9E0T7WFW93
• DSSTox Substance ID: DTXSID3024289
• Nikkaji Number: J2.940H
• Wikipedia: Pyrene
• Wikidata: Q415723
• NCI Thesaurus Code: C1209
• Pharos Ligand ID: NWAR8FUN5F4D
• Metabolomics Workbench ID: 49685
• ChEMBL ID: CHEMBL279564
• Mol file: 129-00-0.mol

Synonyms:pyrene

Chemical Property of Pyrene

Chemical Property:

• Appearance/Colour: Yellow green crystal
• Vapor Pressure: 2.28E-06mmHg at 25°C
• Melting Point: 148 °C
• Refractive Index: 1.851
• Boiling Point: 404 °C at 760 mmHg
• PKA: >15 (Christensen et al., 1975)
• Flash Point: 168.8 °C
• PSA: 0.00000
• Density: 1.248 g/cm³
• LogP: 4.58400
• Storage Temp.: APPROX 4°C
• Solubility.: ethanol: soluble
• Water Solubility.: almost insoluble
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 202.078250319
• Heavy Atom Count: 16
• Complexity: 217

Purity/Quality:

99% ^*data from raw suppliers

Pyrene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,N
• Hazard Codes: N,T+,T,F,Xn
• Statements: 50/53-36/37/38-26-39/23/24/25-23/24/25-11-63-43-45-67-65-38-51/53-52/53-40
• Safety Statements: 60-61-45-36/37-28A-22-16-7-24/25-23-53-62-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC2=C3C(=C1)C=CC4=CC=CC(=C43)C=C2
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
• Effects of Short Term Exposure: Exposure to sun may enhance the irritating effect of this substance. This may result in chronic skin discoloration.
• Uses: It can be used as raw material of organic synthesis. For example, it can be used for production of 1, 4, 5, 8-naphthalene tetracarboxylic acid via oxidation. It can be applied to dyes, synthetic resins and plastics; it can also be used for the manufacturing of vat dye Brilliant Orange GR and various kinds of other dyes. Moreover, it can also be used for the manufacturing of pesticides and plasticizers. Pyrene occurs in coal tar. Also obtained by the destructive hydrogenation of hard coal. Found in wastewater in aquatic environments, and possesses genotoxic characteristics relating to estrogenic/andr ogenic, antiestrogenic and antiandrogenic activity. Pyrene and its derivatives are used commercially to make?dyes?and dye precursors, for example?pyranine?and naphthalene-1,4,5,8-tetracarboxylic acid. It is used as a probe to determine solvent environments and fluorescence spectroscopy. Pyrene may be used as an analytical reference standard for the quantification of the analyte in environmental tobacco smoke samples using high-performance liquid chromatography technique.
• Production method: Pyrene is mainly presented in the distillates of coal tar pitch. Send the asphalt for vacuum distillation under medium temperature; at the same time, directly send a small amount of the overheated steam to the distillation vessel; take the narrow fraction of pyrene and then use the mixed solution of solvent oil and ethanol or a mixed solution of benzene and solvent oil for recrystallization to obtain industrial pyrene with purity of 95%.
• Description: Pyrene is an organic compound with chemical formula C16H10, light yellow monoclinic crystal (pure product is colorless), aromatic, combustible[1], insoluble in water and soluble in ethanol and ether. It can carry out electrophilic substitution, such as halogenation, nitration, sulfonation and other reactions. Pyrene mainly exists in the distillate of coal tar pitch. Pyrene is an organic synthetic raw material, which can be oxidized to produce 1,4,5,8-naphthalene tetracarboxylic acid, which is used in dyes, synthetic resins, disperse dyes and engineering plastics; After acylation, the vat dye brilliant orange GR and other dyes can be prepared. It can also make pesticides, plasticizers, etc. On October 27, 2017, the list of carcinogens published by the international agency for research on cancer of the World Health Organization was preliminarily sorted out for reference. Pyrene was included in the list of three types of carcinogens.
• Physical properties: Colorless solid (tetracene impurities impart a yellow color) or monoclinic prisms crystallized from alcohol. Solutions have a slight blue fluorescence.

Technology Process of Pyrene

There total 277 articles about Pyrene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 15.0%

3-(4H-cyclopentaphenanthrylidene)-1,5-bis(trimethylsilyl)-1,4-pentadiyne (157729-37-8) → pyrene (129-00-0) + benzo[e]pyrene (192-97-2) + 4H-Cyclopenta[def]phenanthrene (203-64-5) + cyclopenta[c,d]pyrene (27208-37-3) + benzo[ghi]fluoranthene (203-12-3) + Coarannulen (5821-51-2)

Guidance literature:

With hydrogen; In gas; at 900 ℃; Product distribution; electrically heated vertical laboratory tubular furnace;

DOI:10.1016/S0040-4039(00)76957-7

Reference yield: 15.0%

3-(4H-cyclopentaphenanthrylidene)-1,5-bis(trimethylsilyl)-1,4-pentadiyne (157729-37-8) → pyrene (129-00-0) + benzo[e]pyrene (192-97-2) + cyclopenta[c,d]pyrene (27208-37-3) + Coarannulen (5821-51-2)

Guidance literature:

With hydrogen; In gas; at 900 ℃; Further byproducts given; electrically heated vertical laboratory tubular furnace;

DOI:10.1016/S0040-4039(00)76957-7

Reference yield:

p-dinitrobenzene - pyrene charge transfer complex → para-dinitrobenzene (100-25-4) + pyrene (129-00-0)

Guidance literature:

In chloroform; at 24 ℃; Equilibrium constant;

upstream raw materials:

[2.2]Metacyclophan

4,5,9,10-tetrahydropyrene

trityl cation

1,2,3,6,7,8-hexahydropyrene

Downstream raw materials:

γ-oxo-1-pyrenebutyric acid

1-bromopyrene

1,2-phthaloyl pyrene

1-(o-carboxybenzoyl)pyrene

Refernces

• 1、 Schnieders, C.,Muellen, K.. "THE ALKALI METAL REDUCTION OF PYRENE-STRUCTURAL AND PREPARATIVE ASPECTS". . p. 1701 - 1712. Retrieved 1984.
• 2、 Campbell,Cromwell,Hager. "". . p. 1051. Retrieved 1936.
• 3、 Hara, Michihiro,Tojo, Sachiko,Kawai, Kiyohiko,Majima, Tetsuro. "Formation and decay of pyrene radical cation and pyrene dimer radical cation in the absence and presence of cyclodextrins during resonant two-photon ionization of pyrene and sodium 1-pyrene sulfonate". . p. 3215 - 3220. Retrieved 2004.
• 4、 Usui, Satoshi,Inoue, Hiroshi,Ishida, Hitoshi,Ohkubo, Katsutoshi. "Laser-Induced Photoionization of Two-Electron-Reduced Viologen". . p. 2089 - 2092. Retrieved 1993.
• 5、 Dijk, Joost T. M. van,Lugtenburg, Johan,Cornelisse, Jan. "Reactivity of the 1-hydropyrenyl anion towards α,ω-dibromoalkanes". . p. 1489 - 1496. Retrieved 1995.
• 6、 Tang, Hao,De Oliveira, Carla Santos,Sonntag, Gage,Gibb, Corinne L. D.,Gibb, Bruce C.,Bohne, Cornelia. "Dynamics of a supramolecular capsule assembly with pyrene". . p. 5544 - 5547. Retrieved 2012.
• 7、 Sturrock,Duncan. "". . p. 2149. Retrieved 1968.
• 8、 Bachmann,Edgerton. "-". . p. 2970,2972. Retrieved 1940.
• 9、 Anderson, Arthur G.,Haddock, Ralph D.. "The Thermal Isomerization of Dicyclopentaheptalene (Azupyrene) to Pyrene". . p. 550 - 552. Retrieved 1991.
• 10、 Pankasem, Surapol,Thomas, J. Kerry. "Reflectance Spectroscopic Studies of the Cation Radical and the Triplet of Pyrene on Alumina". . p. 6990 - 6996. Retrieved 1991.