Benz(A)anthracene-5,6-dione

Base Information

• Chemical Name: Benz(A)anthracene-5,6-dione
• CAS No.: 18508-00-4
• Molecular Formula: C18H10O2
• Molecular Weight: 258.276
• NSC Number: 171732
• UNII: 2NC1XEJ6RT
• DSSTox Substance ID: DTXSID10171710
• Nikkaji Number: J1.557.289B
• Wikidata: Q83041848
• Mol file: 18508-00-4.mol

Synonyms:18508-00-4;BENZ(A)ANTHRACENE-5,6-DIONE;2NC1XEJ6RT;Benz[a]anthracene-5,6-dione;Benz(alpha)anthracene-5,6-dione;NSC 171732;NSC-171732;benzo[a]anthracene-5,6-dione;UNII-2NC1XEJ6RT;SCHEMBL2198881;DTXSID10171710;O-BENZ(A)ANTHRACENEQUINONE;NSC171732;5,6-BENZ(A)ANTHRACENEQUINONE;1,2-BENZO-3,4-ANTHRAQUINONE;BENZ(A)ANTHRACENE-5,6-QUINONE

Chemical Property of Benz(A)anthracene-5,6-dione

Chemical Property:

• Vapor Pressure: 1.59E-09mmHg at 25°C
• Boiling Point: 484°C at 760 mmHg
• Flash Point: 210.3°C
• Density: 1.336g/cm³
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 258.068079557
• Heavy Atom Count: 20
• Complexity: 427

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C=C3C(=CC2=C1)C4=CC=CC=C4C(=O)C3=O

Technology Process of Benz(A)anthracene-5,6-dione

There total 2 articles about Benz(A)anthracene-5,6-dione 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:

benz[a]anthracene (56-55-3) → benz[a]anthracene-7,12-dione (2498-66-0) + benzo[a]anthracene-5,6-dione (18508-00-4)

Guidance literature:

With ozone; In dichloromethane; at 25 ℃; Rate constant; Mechanism; correlations of relative rate data with various molecular orbital parameters;

DOI:10.1021/jo00171a008

Reference yield:

(+/-)-benzanthracene-5,6-epoxide (962-32-3) → benzo[a]anthracene-5,6-dione (18508-00-4) + 5-hydroxybenzanthracene (960-92-9) + 5-hydroxybenzanthracene (56183-17-6) + (+/-)-cis-5,6-Dihydroxy-5,6-dihydrobenzanthracene (78307-15-0) + cis-5,6-dihydroxy-5,6-dihydrobenzanthracene (67315-17-7)

Guidance literature:

With water; In 1,4-dioxane; at 25 ℃; Rate constant; Product distribution; solvent effects (acid-catalyzed methanolysis), substituent effects;

DOI:10.1021/ja00010a036

Reference yield: 91.0%

benzo[a]anthracene-5,6-dione (18508-00-4) → cis-5,6-dihydroxy-5,6-dihydrobenzanthracene (67315-17-7)

Guidance literature:

With sodium tetrahydroborate; oxygen; In ethanol; for 24h; Ambient temperature;

DOI:10.1055/s-1982-29834

upstream raw materials:

(+/-)-benzanthracene-5,6-epoxide

benz[a]anthracene

Downstream raw materials:

cis-5,6-dihydroxy-5,6-dihydrobenzanthracene

3-(2-carboxy-phenyl)-[2]naphthoic acid

dibenzo[a,c]anthracene

Refernces

• 1、 Pryor, William A.,Gleicher, Gerald J.,Church, Daniel F.. "Reaction of Polycyclic Aromatic Hydrocarbons with Ozone. Linear Free-Energy Relationships and Tests of Likely Rate-Determining Steps Using Simple Molecular Orbital Correlations". . p. 4198 - 4202. Retrieved 2007/10/02.