3-Hydroxybenz[a]anthracene

Base Information

• Chemical Name: 3-Hydroxybenz[a]anthracene
• CAS No.: 4834-35-9
• Molecular Formula: C18H12O
• Molecular Weight: 244.2873
• DSSTox Substance ID: DTXSID2038318
• Nikkaji Number: J650.401I
• Wikidata: Q81984094
• Mol file: 4834-35-9.mol

Synonyms:3-hydroxybenz(a)anthracene;3-OH-BaA

Chemical Property of 3-Hydroxybenz[a]anthracene

Chemical Property:

• Vapor Pressure: 1.5E-10mmHg at 25°C
• Boiling Point: 498.2°Cat760mmHg
• Flash Point: 240.4°C
• PSA: 20.23000
• Density: 1.284g/cm³
• LogP: 4.85180
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 244.088815002
• Heavy Atom Count: 19
• Complexity: 326

Purity/Quality:

99%min ^*data from raw suppliers

Benz[a]anthracen-3-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C=C3C(=CC2=C1)C=CC4=C3C=CC(=C4)O
• Uses: 3-Hydroxybenz[a]anthracene is a derivative of the most potent carcinogenic hydrocarbon, 7,12-Dimethylbenz[a]anthracene (D464500), a highly potent carcinogen that is activated by microsomal enzymes to a diol epoxide metabolite that binds covalently to DNA in mammalian cells, leading ultimately to tumor induction. Benz[a]anthracen-3-ol is used in carcinogenesis studies relating to breast cancer.

Technology Process of 3-Hydroxybenz[a]anthracene

There total 7 articles about 3-Hydroxybenz[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: 89.0%

3,7,12-trimethoxybenz[a]anthracene (671780-75-9) → 3-hydroxybenzanthracene (4834-35-9)

Guidance literature:

With hydrogen iodide; acetic acid; for 48h; Heating;

DOI:10.1021/jo030348n

Reference yield: 81.0%

3-methoxybenzanthracene (69847-25-2) → 3-hydroxybenzanthracene (4834-35-9)

Guidance literature:

With hydrogen bromide; In acetic acid; for 3.5h; Heating;

DOI:10.1021/jm00396a023

Reference yield:

(+/-)-trans-3,4-dihydroxy-3,4-dihydrobenzanthracene (60967-89-7,64501-86-6,60839-18-1,67335-42-6,67335-43-7) → 3-hydroxybenzanthracene (4834-35-9) + 4-hydroxybenzoanthracene (5133-12-0)

Guidance literature:

With phosphoric acid; In methanol; at 60 ℃; for 5h; Yield given. Yields of byproduct given;

DOI:10.1021/jo00334a010

upstream raw materials:

3-methoxybenzanthracene

(+/-)-trans-3,4-dihydroxy-3,4-dihydrobenzanthracene

3-Oxo-1,2,3,4,7,12-tetrahydrobenzanthracen

3,7,12-trimethoxybenz[a]anthracene

Downstream raw materials:

benzanthracene-3,4-dione

3-methoxybenzanthracene

(+/-)-trans-3,4-dihydroxy-3,4-dihydrobenzanthracene

(+/-)-trans-3,4-dihydroxy-1,2,3,4-tetrahydrobenzanthracene

Refernces

• 1、 Harvey,Cortez,Sugiyama,Ito,Sawyer,DiGiovanni. "Biologically active dihydrodiol metabolites of polycyclic aromatic hydrocarbons structurally related to the potent carcinogenic hydrocarbon 7,12-dimethylbenz[a]anthracene". . p. 154 - 159. Retrieved 2007/10/02.