3-Hydroxy-7,12-dimethylbenz(a)anthracene

Base Information

• Chemical Name: 3-Hydroxy-7,12-dimethylbenz(a)anthracene
• CAS No.: 57266-83-8
• Molecular Formula: C₂₀H₁₆O
• Molecular Weight: 272.346
• UNII: M347XX7DJX
• DSSTox Substance ID: DTXSID70205888
• Nikkaji Number: J73.199D
• Mol file: 57266-83-8.mol

Synonyms:3-hydroxy-7,12-dimethylbenz(a)anthracene;3-hydroxy-DMBA

Chemical Property of 3-Hydroxy-7,12-dimethylbenz(a)anthracene

Chemical Property:

• Vapor Pressure: 2.18E-11mmHg at 25°C
• Melting Point: 167-168 °C
• Boiling Point: 518.9°Cat760mmHg
• PKA: 9.76±0.30(Predicted)
• Flash Point: 247.7°C
• PSA: 20.23000
• Density: 1.222g/cm³
• LogP: 5.46860
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 272.120115130
• Heavy Atom Count: 21
• Complexity: 378

Purity/Quality:

99% ^*data from raw suppliers

3-HYDROXY-7,12-DIMETHYLBENZ(A)ANTHRACENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C=CC3=C(C2=C(C4=CC=CC=C14)C)C=CC(=C3)O

Technology Process of 3-Hydroxy-7,12-dimethylbenz(a)anthracene

There total 9 articles about 3-Hydroxy-7,12-dimethylbenz(a)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: 95.0%

3-methoxy-7,12-dimethylbenzanthracene (66240-02-6) → 3-hydroxy-7,12-dimethylbenzanthracene (57266-83-8)

Guidance literature:

With lithium methanethiolate; In N,N-dimethyl-formamide; for 4h; Heating;

DOI:10.1021/jo01310a029

Reference yield:

3-methoxy-7-(chloromethyl)-12-methylbenzanthracene (66240-01-5) → 3-hydroxy-7,12-dimethylbenzanthracene (57266-83-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / NaBH₄ / dimethylsulfoxide / 5 h / Ambient temperature

2: 95 percent / lithium thiomethoxide / dimethylformamide / 4 h / Heating

With sodium tetrahydroborate; lithium methanethiolate; In dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo01310a029

Reference yield:

7,12-Dimethyl-7,12-dihydro-benzo[a]anthracene-3,7,12-triol (103500-33-0) → 3-hydroxy-7,12-dimethylbenzanthracene (57266-83-8)

Guidance literature:

With lithium aluminium tetrahydride; titanium(III) chloride; In tetrahydrofuran; for 2h; Yield given; Heating;

DOI:10.1021/jo00368a021

upstream raw materials:

3-methoxy-7,12-dimethylbenzanthracene

7,12-Dimethyl-7,12-dihydro-benzo[a]anthracene-3,7,12-triol

3-oxo-1,2,3,4,5,6-hexahydrobenzo(a)anthracene

3-hydroxybenzo(a)anthracene acetate

Downstream raw materials:

7,12-dimethylbenzanthracene-3,4-dione

3,4-dihydroxy-7,12-dimethylbenzanthracene

(+/-)-trans-3,4-Dihydroxy-3,4-dihydro-7,12-dimethylbenzanthracene

7,12-dimethylbenz[a]anthracene anti-diol epoxide

Refernces

A new synthesis of trans-3,4-dihydroxy-anti-1,2-epoxy-1,2,3,4-tetrahydro-7,12- dimethylbenz(a)anthracene

10.1080/00397919308009793

The research details a new and efficient synthesis method for trans-3,4-dihydroxy-anti-1,2-epoxy-1,2,3,4-tetrahydro-7,12-dimethylbenz(a)anthracene, a highly carcinogenic metabolite of 7,12-dimethylbenz(a)anthracene (DMBA). The purpose of this study is to provide a facile synthesis approach for this compound, which is significant due to its role as the principal active form of DMBA that binds covalently to DNA in vivo, implicated in carcinogenesis. The synthesis involves key intermediates such as 3-hydroxy-7,12-dimethylbenz(a)anthracene, which is derived from 2-bromo-1,4-dimethylnaphthalene through a series of reactions including Grignard reactions, bromination, and cyclization with polyphosphoric acid (PPA).