3-Acetoxydibenz[a,h]anthracene

Base Information

• Chemical Name: 3-Acetoxydibenz[a,h]anthracene
• CAS No.: 72378-87-1
• Molecular Formula: C24H16O2
• Molecular Weight: 336.39
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID70370626
• Wikidata: Q82157750
• Mol file: 72378-87-1.mol

Synonyms:3-Acetoxydibenz[a,h]anthracene;72378-87-1;naphtho[1,2-b]phenanthren-3-yl acetate;Benzo[k]benz[a]anthracen-3-ol,3-acetate;DTXSID70370626;AKOS030240203;AB05542;FT-0661078

Chemical Property of 3-Acetoxydibenz[a,h]anthracene

Chemical Property:

• Vapor Pressure: 1.63E-13mmHg at 25°C
• Melting Point: 247-248 °C
• Refractive Index: 1.764
• Boiling Point: 581.5 °C at 760 mmHg
• Flash Point: 170.5 °C
• PSA: 26.30000
• Density: 1.276 g/cm³
• LogP: 6.22470
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 336.115029749
• Heavy Atom Count: 26
• Complexity: 528

Purity/Quality:

98%Min ^*data from raw suppliers

3-Acetoxydibenz[a,h]anthracene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1=CC2=C(C=C1)C3=CC4=C(C=C3C=C2)C5=CC=CC=C5C=C4
• Uses: 3-Acetoxydibenz[a,h]anthracene is used in the synthesis of 3-Hydroxydibenz[a,h]anthracene, known to be a metabolite of DBA (Dibenz[a,h]anthracene) (D417010).

Technology Process of 3-Acetoxydibenz[a,h]anthracene

There total 3 articles about 3-Acetoxydibenz[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: 74.0%

3-acetoxy-1,2-dihydrodibenzanthracene (72378-86-0) → 3-acetoxydibenzanthracene (72378-87-1)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; for 1.5h; Heating;

DOI:10.1021/jo01292a007

Reference yield:

trans-3,4-diacetoxy-1,2,3,4-tetrahydrodibenzanthracene (66267-14-9) → 3-acetoxydibenzanthracene (72378-87-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) p-tosic acid; 2.) isopropenylacetate, acetic anhydride. / 1.) benzene, reflux, 1.5 h; 2.) reflux, overnight.

2: 74 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / benzene / 1.5 h / Heating

With Isopropenyl acetate; acetic anhydride; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene;

DOI:10.1021/jo01292a007

Reference yield:

3-hydroxydibenzanthracene (1421-80-3) → 3-acetoxydibenzanthracene (72378-87-1)

Guidance literature:

With pyridine; for 16h; Yield given; Ambient temperature;

DOI:10.1021/jo00148a019

upstream raw materials:

3-acetoxy-1,2-dihydrodibenzanthracene

3-hydroxydibenzanthracene

trans-3,4-diacetoxy-1,2,3,4-tetrahydrodibenzanthracene

Downstream raw materials:

3-hydroxydibenzanthracene

Refernces

• 1、 Lee, Hong Mee,Harvey, Ronald G.. "Synthesis of Biologically Active Metabolites of Dibenzanthracene". . p. 588 - 592. Retrieved 2007/10/02.