Anthracene

Base Information

• Chemical Name: Anthracene
• CAS No.: 120-12-7
• Deprecated CAS: 2417305-12-3
• Molecular Formula: C14H10
• Molecular Weight: 178.233
• Hs Code.: 2902.90
• European Community (EC) Number: 204-371-1
• ICSC Number: 0825
• NSC Number: 7958
• UN Number: 1137
• UNII: EH46A1TLD7
• DSSTox Substance ID: DTXSID0023878
• Nikkaji Number: J2.916E,J3.643.785E
• Wikipedia: Anthracene
• Wikidata: Q422152
• NCI Thesaurus Code: C251
• Metabolomics Workbench ID: 52118
• ChEMBL ID: CHEMBL333179
• Mol file: 120-12-7.mol

Synonyms:Green Oil;Anthracene, pure;Tetra Olive N2G;Coal tar pitch volatiles: anthracene;Anthracin;Anthracene oil (coal tar fraction);Anthracene (C14H10);Bis-alkylamino anthracene;Paranaphthalene;

Chemical Property of Anthracene

Chemical Property:

• Appearance/Colour: colourless crystalline solid
• Vapor Pressure: 1 mm Hg ( 145 °C)
• Melting Point: 215-218 °C
• Refractive Index: 1.5948
• Boiling Point: 337.355 °C at 760 mmHg
• PKA: >15 (Christensen et al., 1975)
• Flash Point: 146.606 °C
• PSA: 0.00000
• Density: 1.13 g/cm³
• LogP: 3.99300
• Storage Temp.: APPROX 4°C
• Solubility.: toluene: soluble20mg/mL, clear, colorless to faintly yellow
• Water Solubility.: 0.045 mg/L (25 ºC)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 178.078250319
• Heavy Atom Count: 14
• Complexity: 154

Purity/Quality:

99% ^*data from raw suppliers

Anthracene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N,F
• Hazard Codes: Xi,N,F,T,Xn
• Statements: 36/37/38-50/53-67-36-11-39/23/24/25-23/24/25-65-38-66-51/53
• Safety Statements: 26-60-61-24/25-16-9-45-36/37-62-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C2C=C3C=CC=CC3=CC2=C1
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly.
• Effects of Short Term Exposure: The substance is mildly irritating to the skin and respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis under the influence of UV light.
• Description: Anthracene is one of a group of chemicals called polycyclic aromatic hydrocarbons (PAHs). PAHs are often found together in groups of two ormore. They can exist inmore than 100 different combinations, but the most common are treated as a group of 15. PAHs are found naturally in the environment but they can also be made synthetically. Anthracene can vary in appearance from a colorless to pale yellow crystal-like solid. PAHs are created when products like coal, oil, gas, and garbage are burned but the burning process is not complete. Very little information is available on the individual chemicals within the PAH group; the majority of the information is for the entire PAH group. Anthracene is a solid white to yellow crystal, has a weak aromatic odor, and sinks in water. Its characteristics are boiling point, 3421°C; melting point, 2181°C; molecular weight, 178.22; density/specific gravity, 1.25 at 27 and 41°C; octanol–water coefficient, 4.45. It is soluble in absolute alcohol and organic solvents. Maximum absorption occurs at 218 nm.
• Physical properties: White to yellow crystalline flakes or crystals with a bluish or violet fluorescence and a weak aromatic odor. Impurities (naphthacene, tetracene) impart a yellowish color with green fluorescence.
• Uses: Anthracene has been shown to be soluble in a variety of binary and ternary mixtures of cyclohexanone, ethyl acetate, and methanol 1,2. Anthracene is an aromatic hydrocarbonwith three fused rings, and is obtained by the distillationof crude oils. The main useis in the manufacture of dyes.It is an important source of dyestuffs. Most of the PAHs are used to conduct research. Like most PAHs, anthracene is used to make dyes, plastics, and pesticides. It has been used to make smoke screens and scintillation counter crystals. (A scintillation counter is used to detect or count the number of sparks or flashes that occur over a period of time.)

Technology Process of Anthracene

There total 1087 articles about Anthracene 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:

1,4-dihydroxy-5-methylanthracene-9,10-dione (858277-53-9) → anthracene (120-12-7) + 1-methylanthracene (610-48-0) + 2-methylanthracene (613-12-7)

Guidance literature:

bei der Zinkstaub-Destillation;

Reference yield:

suberene (256-81-5) + di-tert-butyl nitroxide (2406-25-9,44871-19-4) → anthracene (120-12-7) + 9-methylanthracene (779-02-2) + benzocycloheptatrien (264-08-4) + 1-methylanthracene (610-48-0) + 2-methylanthracene (613-12-7) + C18H18

Guidance literature:

With naphthalene; In neat (no solvent); at 345 ℃; for 1h; under 15 Torr; Product distribution;

DOI:10.1021/jo01289a028

Reference yield:

suberene (256-81-5) → dibenzosuberane (833-48-7) + 9,10-dihydroanthracene (613-31-0) + anthracene (120-12-7) + 9-methylanthracene (779-02-2) + 1-methylanthracene (610-48-0) + 2-methylanthracene (613-12-7)

Guidance literature:

In neat (no solvent); at 400 ℃; for 24h; under 15 Torr; Product distribution;

DOI:10.1021/jo01289a028

upstream raw materials:

naphthalene

3-(4'-hydroxyphenyl)phthalide

9-ethyl-9,10-dihydroanthracene

ethylbenzene

Downstream raw materials:

11-phenyl-9,10-dihydro-9,10-ethano-anthracene

9,10-phenanthrenequinone

9,10-dihydro-9,10-ethanoanthracene-11-carboxylic acid

9-Bromoanthracene

Refernces

• 1、 Zhang, Wei,Ma, Hong,Zhou, Lipeng,Sun, Zhiqiang,Du, Zhongtian,Miao, Hong,Xu, Jie. "Organocatalytic oxidative dehydrogenation of dihydroarenes by dioxygen using 2,3-dichloro-5,6-dicyano-benzoquinone (DDQ) and NaNO2". . p. 3236 - 3245. Retrieved 2008.
• 2、 Leute,Winstein. "". . p. 2475. Retrieved 1967.
• 3、 Aleandri, Lorraine E.,Bogdanovic, Borislav,Duerr, Christine,Huckett, Sara C.,Jones, Deborah J.,Kolb, Uwe,Lagarden, Martin,Roziere, Jacques,Wilczok, Ursula. "Investigation of the formation reaction and structural characterization of the 'platinum Grignard reagent' [Pt(MgCl)2(THF)(x)] by extended X-ray absorption fine structure (EXAFS) and other methods". . p. 1710 - 1718. Retrieved 1997.
• 4、 Kuimov, Vladimir A.,Gusarova, Nina K.,Malysheva, Svetlana F.,Trofimov, Boris A.. "Transition metal-free regioselective access to 9,10-dihydroanthracenes via the reaction of anthracenes with elemental phosphorus in the KOH/DMSO system". . p. 4533 - 4536. Retrieved 2018.
• 5、 Barber, Richard A.,Mayo, Paul de,Okada, Keiji,Wong, S. King. "Photosensitized Cycloreversion of Anthracene Dimer via an Electron-Transfer Mechanism". . p. 4995 - 4997. Retrieved 1982.
• 6、 Lechner, Manuel,Kastner, Katharina,Chan, Chee Jian,Güttel, Robert,Streb, Carsten. "Aerobic Oxidation Catalysis by a Molecular Barium Vanadium Oxide". . p. 4952 - 4956. Retrieved 2018.
• 7、 Amtawong, Jaruwan,Balcells, David,Skjelstad, Bastian B.,Tilley, T. Don. "Concerted Proton-Electron Transfer Reactivity at a Multimetallic Co4O4Cubane Cluster". . p. 15553 - 15560. Retrieved 2020.
• 8、 Kosai, Tomoyuki,Ishida, Shintaro,Iwamoto, Takeaki. "A Two-Coordinate Cyclic (Alkyl)(amino)silylene: Balancing Thermal Stability and Reactivity". . p. 15554 - 15558. Retrieved 2016.
• 9、 Coggins, Michael K.,Toledo, Santiago,Kovacs, Julie A.. "Isolation and characterization of a dihydroxo-bridged iron(III,III)(μ- OH)2 diamond core derived from dioxygen". . p. 13325 - 13331. Retrieved 2013.
• 10、 Prelog et al.. "". . p. 434,438. Retrieved 1955.