Dibenz[a,h]anthracene

Base Information

• Chemical Name: Dibenz[a,h]anthracene
• CAS No.: 53-70-3
• Molecular Formula: C22H14
• Molecular Weight: 278.353
• Hs Code.: 2902909090
• European Community (EC) Number: 200-181-8
• ICSC Number: 0431
• NSC Number: 22433
• UN Number: 3077
• UNII: T30ELH3D5X
• DSSTox Substance ID: DTXSID9020409
• Nikkaji Number: J2.797I
• Wikipedia: Dibenz(a,h)anthracene
• Wikidata: Q4140494
• NCI Thesaurus Code: C951
• Pharos Ligand ID: D511XXK1MWGM
• Metabolomics Workbench ID: 52119
• ChEMBL ID: CHEMBL1346946
• Mol file: 53-70-3.mol

Synonyms:1,2,5,6-dibenzanthracene;1,2,5,6-dibenzanthracene, ion(1+);1,2,5,6-dibenzanthracene, ion(1-);dibenz(a,h)anthracene;dibenzo(a,h)anthracene

Chemical Property of Dibenz[a,h]anthracene

Chemical Property:

• Appearance/Colour: white to light yellow crystalline solid
• Vapor Pressure: 1.41E-10mmHg at 25°C
• Melting Point: 262-265 °C(lit.)
• Refractive Index: 1.8120 (estimate)
• Boiling Point: 524 °C(lit.)
• Flash Point: 264.5°C
• PSA: 0.00000
• Density: 1.232g/cm³
• LogP: 6.29940
• Storage Temp.: APPROX 4°C
• Solubility.: Soluble in petroleum ether, benzene, toluene, xylene, and oils (Windholz et al., 1983).
• Water Solubility.: 2.2ug/L(25 oC)
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 278.109550447
• Heavy Atom Count: 22
• Complexity: 361
• Transport DOT Label: Class 9

Purity/Quality:

Dibenz[a,h]anthracene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A confirmed carcinogen. A poison.
• Hazard Codes: T,N,F
• Statements: 45-50/53-67-65-38-11-52/53-36/37/38
• Safety Statements: 53-45-60-61-62-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C2C(=C1)C=CC3=CC4=C(C=CC5=CC=CC=C54)C=C32
• Inhalation Risk: A nuisance-causing concentration of airborne particles can be reached quickly when dispersed.
• Effects of Long Term Exposure: The substance may have effects on the skin. This may result in photosensitization. This substance is probably carcinogenic to humans.
• Description: 1, 2:5, 6-DIBENZANTHRACENE is a crystalline aromatic hydrocarbon. It is a component of coal tars, shale oils, and soots (IARC, 1985) and has been detected in gasoline engine exhaust, coke oven emissions, cigarette smoke, charcoal broiled meats, vegetation near heavily traveled roads, and surface water and soils near hazardous waste sites. It is a kind of carcinogenic compound, and thus being mainly used for the research purpose. For example, in biological research, it is a mutagen used to induce tumorigenesis.
• Physical properties: Colorless to pale yellow, monoclinic or orthorhombic crystals which with a faint, pleasant odor.
• Uses: Dibenz[a,h]anthracene is a polycyclic aromatic hydrocarbon (PAH) and a known carcinogen. Dibenz[a,h]anthracene has produced positive results in bacterial DNA damage and mutagenicity assays and in mammalian cell DNA damage, mutagenicity and cell transformation assays. There is no report on the common use of dibenz[a,h]anthracene and its commercial production.

Technology Process of Dibenz[a,h]anthracene

There total 93 articles about Dibenz[a,h]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: 100.0%

1a,13b-dihydrodibenz<3,4:7,8>anthra<1,2-b>oxirene → dibenzo[a,h]anthracene (53-70-3)

Guidance literature:

With lithium; In tetrahydrofuran; 1.) 0 deg C, 3 h, 2.) -18 deg C, 16 d;

Reference yield: 99.0%

1a,13b-dihydro-1H-dibenz<3,4:7,8>anthra<1,2-b>azirine (71382-49-5) → dibenzo[a,h]anthracene (53-70-3)

Guidance literature:

With sodium; In tetrahydrofuran; 1.) 0 deg C, 3 h, 2.) -18 deg C, 14 d;

Reference yield: 93.0%

dibenzanthracen-7-ol acetate (63077-06-5) → dibenzo[a,h]anthracene (53-70-3)

Guidance literature:

With potassium hydroxide; zinc; In 1,4-dioxane; water; Heating;

DOI:10.1021/jo00132a026

upstream raw materials:

(2-methylnaphthalen-1-yl)(naphthalen-1-yl)methanone

(2-methyl-[1]naphthyl)-[2]naphthyl ketone

1-[2]naphthylmethyl-[2]naphthoic acid

(E)-3-Ureido-but-2-enoic acid ethyl ester

Downstream raw materials:

dibenzanthracene 5,6-oxide

5,6-dihydrodibenzanthracene

5,6,12,13-tetrahydrodibenzanthracene

dibenzo[a,h]anthracene-7,14-dione

Refernces

• 1、 Minsky, Abraham,Meyer, Amatzya Y.,Rabinovitz, Mordecai. "(1)H NMR PATTERNS OF ANTIAROMATIC SYSTEMS: PARATROPIC DISPLACEMENT DEPENDENCE UPON LUMO-HOMO ENERGY GAP". . p. 5351 - 5354. Retrieved 1982.
• 2、 Martínez, Jose I.,Mora-Fuentes, Juan P.,Carini, Marco,Saeki, Akinori,Saeki, Akinori,Melle-Franco, Manuel,Mateo-Alonso, Aurelio,Mateo-Alonso, Aurelio. "Dibenzoanthradiquinone Building Blocks for the Synthesis of Nitrogenated Polycyclic Aromatic Hydrocarbons". supporting information. p. 4737 - 4741. Retrieved 2020/06/29.
• 3、 Wakabayashi, Ryota,Kurahashi, Takuya,Matsubara, Seijiro. "Synthesis of phenanthrenes by cationic chromium(III) porphyrin-catalyzed dehydration cycloaromatization". supporting information. p. 2297 - 2301. Retrieved 2013/11/06.