215-58-7

Basic information

• Product Name: 1,2:3,4-DIBENZANTHRACENE
• Synonyms: 94652, Dibenz[a,c]anthracene (purity);1,2,3,4-1,2,3,4-Dibenzanthracene;1,2,3,4-DIBENZANTHRACENE 97%;Dibenz[a,c]anthracene solution;1,2,3,4-Dibenzanthracene,97%;1.2:3.4-Dibenzanthracene 10mg [215-58-7];Dibenz[a,c]anthracene,1,2:3,4-Dibenzanthracene;1,2,3,4-Dibenzanthracene, 97% 100MG
• CAS NO: 215-58-7
• Molecular Formula: C₂₂H₁₄
• Molecular Weight: 278.35
• EINECS: 205-920-8
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives
• Mol File: 215-58-7.mol
• Article Data: 22

Chemical Properties

• Melting Point: 205-207 °C(lit.)
• Boiling Point: 518 °C(lit.)
• Flash Point: -18 °C
• Appearance: /
• Density: 1.1489 (estimate)
• Vapor Pressure: 2.55E-10mmHg at 25°C
• Refractive Index: 1.8120 (estimate)
• Storage Temp.: APPROX 4°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), DMSO (Slightly)
• Water Solubility: 1.6ug/L(25 oC)
• BRN: 1912415
• CAS DataBase Reference: 1,2:3,4-DIBENZANTHRACENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:3,4-DIBENZANTHRACENE(215-58-7)
• EPA Substance Registry System: 1,2:3,4-DIBENZANTHRACENE(215-58-7)

Safety Data

• Hazard Codes: T,N,Xn,F
• Statements: 23/24/25-50-67-65-50/53-38-11
• Safety Statements: 36/37-45-61-62-60
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: DM1925000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 215-58-7(Hazardous Substances Data)

Usage

Chemical Properties

LIGHT YELLOW TO BROWN POWDER

Uses

Dibenzo[a,c]anthracene is a polycyclic aromatic hydrocarbon which are known carcinogens and environmental pollutants.

Safety Profile

Questionable carcinogen withexperimental tumorigenic data. Human mutation datareported. When heated to decomposition it emits acridsmoke and irritating fumes.

Carcinogenicity

Dibenz[a,c]anthracene was administered dermally to mice, either per se or as part of initiation–promotion protocols. The working group concluded that there was limited evidence for animal carcinogenicity. In later studies on an initiation–promotion study on mouse skin, low initiating doses gave negative results when administered subcutaneously to mice, and tumor incidence was not significantly increased over that observed in controls when the compound was administered intraperitoneally to newborn mice.

InChI:InChI=1/C22H14/c1-2-8-16-14-22-20-12-6-4-10-18(20)17-9-3-5-11-19(17)21(22)13-15(16)7-1/h1-14H

Upstream product

• 3228-74-8 dibenzanthracene-9,14-dione 
• 85-01-8 phenanthrene 
• 933-88-0 ortho-toluoyl chloride 
• 860595-49-9 2-(1,2,3,4,5,6,7,8-octahydro-phenanthrene-9-carbonyl)-benzoic acid 
• 91-13-4 α,α'-dibromo-o-xylene 
• 189999-35-7 [1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate 
• 93-09-4 naphthalene-2-carboxylate 
• 591-50-4 iodobenzene 
• 22082-97-9 1-bromo-2-(2-naphthyl)benzene 
• 66003-76-7 Diphenyliodonium triflate 
• 132-64-9 dibenzofuran 
• 143-66-8 sodium tetraphenyl borate 
• 243-46-9 benzo[b]naphtho[2,3-d]thiophene 

Downstream Products

• 39081-15-7 10-hydroxydibenz[a,c]anthracene 
• 83314-29-8 9-nitrodibenzanthracene 
• 25486-89-9 10,11,12,13-tetrahydrodibenzanthracene 

Relevant articles and documents

Triple Benzannulation of Naphthalene via a 1,3,6-Naphthotriyne Synthetic Equivalent. Synthesis of Dibenz[a,c]anthracene

A new synthesis of dibenzo[a,c]anthracene (4) is described that features the generation, from tetrabromo-bis-triflate 1 and phenyllithium, of a 1,3,6-naphthotriyne (2) synthetic equivalent that is trapped with 3 equiv of furan to form Diels-Alder tris-adduct 3. A subsequent two-step deoxygenation of 3 represents the first synthesis of dibenz[a,c]anthracene (4) that involves a tandem aryne Diels-Alder cycloaddition-deoxygenation strategy.

Palladium Catalyzed C-I and Vicinal C-H Dual Activation of Diaryliodonium Salts for Diarylations: Synthesis of Triphenylenes

Using the synthetic strategy of palladium-catalyzed dual activation of both C-I and vicinal C-H bonds of diaryliodonium salts, we report an approach for direct diarylations of 2-bromobiphenyls or bromobenzenes. As a result, a wide range of triphenylenes with various substituents have been synthesized in good yields. These triphenylenes are expected to be employed in the "bottom-up" synthesis of functional aromatic molecules in material science.

Synthesis and characterization of oxadisilole fused benzo[b]triphenylene

Palladium-catalyzed [2+2+2] cyclotrimerization reactions between benzyne and oxadisilole fused oxabicyclic alkenes afforded the exo-adducts. Deoxygenation with BF3·OMe2 yielded mono- and bis-oxadisilole fused benzo[b]triphenylene. The photophysical properties of the oxadisilole fused benzo[b]triphenylenes were characterized.

Aluminium-mediated aromatic C-F bond activation: Regioswitchable construction of benzene-fused triphenylene frameworks

Selective synthesis of benzo[f]tetraphenes or benzo[g]chrysenes was achieved via aromatic C-F bond cleavage and unprecedented regioselective C-C bond formation depending upon the choice of aluminium reagents. On treatment with AlCl3, 2-(bipheny

Two-in-One Strategy for the Pd(II)-Catalyzed Tandem C-H Arylation/Decarboxylative Annulation Involved with Cyclic Diaryliodonium Salts

We report here a two-in-one strategy for the Pd(II)-catalyzed tandem C-H arylation/decarboxylative annulation between readily available cyclic diaryliodonium salts and benzoic acids. The carboxylic acid functionality can be used as both a directing group for the ortho-C-H arylation and the reactive group for the tandem decarboxylative annulation. By a step-economical double cross-coupling annulation procedure, the privileged triphenylene frameworks were efficiently constructed, which have potential applications in material chemistry.

Aromatic Metamorphosis of Dibenzofurans into Triphenylenes Starting with Nickel-Catalyzed Ring-Opening C-O Arylation

A new class of aromatic metamorphosis has been developed in which dibenzofurans were converted into triphenylenes. This transformation is composed of three successive operations: (1) nickel-catalyzed ring-opening C-O bond arylation with arylmagnesium bromides, (2) trifluoromethanesulfonylation (triflation) of the resulting hydroxy moiety with Tf2O, and (3) palladium-catalyzed or photoinduced ring closure. In the last ring-closing step, the photoinduced process has proven to be more productive than the palladium-catalyzed one. By employing π-extended dinaphthofuran as the substrate, dorsally benzo-fused [5]helicene was obtained in a satisfactory yield.