1,2-Benzanthraquinone

Base Information

• Chemical Name: 1,2-Benzanthraquinone
• CAS No.: 2498-66-0
• Deprecated CAS: 129243-38-5,138424-87-0,138424-87-0
• Molecular Formula: C18H10O2
• Molecular Weight: 258.276
• Hs Code.: 29146990
• European Community (EC) Number: 219-693-8
• NSC Number: 7961
• UNII: BL89U5YZBK
• DSSTox Substance ID: DTXSID8051916
• Nikkaji Number: J7.596E
• Wikidata: Q27274742
• Mol file: 2498-66-0.mol

Synonyms:1,2-benzanthraquinone;7,12-benz(a)anthraquinone;benz(a)anthracene-7,12-dione

Chemical Property of 1,2-Benzanthraquinone

Chemical Property:

• Appearance/Colour: yellow to green crystalline powder
• Vapor Pressure: 4.24E-09mmHg at 25°C
• Melting Point: 167-168ºC
• Refractive Index: 1.722
• Boiling Point: 472.5 °C at 760 mmHg
• Flash Point: 175.5 °C
• PSA: 34.14000
• Density: 1.336 g/cm³
• LogP: 3.61520
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 4.1
• 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% ^*data from raw suppliers

Benz[a]anthracene-7,12-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC3=C2C(=O)C4=CC=CC=C4C3=O
• General Description: 1,2-Benzanthraquinone is a key intermediate used in the synthesis of various benzanthracene derivatives, particularly those with potential estrogenic and carcinogenic properties. In this study, it served as a starting material for the preparation of 9,10-dialkyl-9,10-dihydroxy-9,10-dihydro-1,2-benzanthracenes, where alkyl groups were introduced via Grignard reactions. The resulting derivatives demonstrated varying degrees of estrogenic activity, with ethyl and n-propyl-substituted compounds showing notable effects in biological assays. The findings highlight the role of 1,2-benzanthraquinone as a precursor in exploring structure-activity relationships for compounds with hormonal and carcinogenic potential.

Technology Process of 1,2-Benzanthraquinone

There total 66 articles about 1,2-Benzanthraquinone 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: 88.0%

2-(naphthalene-1-carbonyl)-benzoic acid (5018-87-1) → benz[a]anthracene-7,12-dione (2498-66-0)

Guidance literature:

With phosphorus pentoxide; at 180 - 200 ℃; vacuum;

Reference yield: 87.0%

C22H18O2 → benz[a]anthracene-7,12-dione (2498-66-0)

Guidance literature:

In benzene; Irradiation;

DOI:10.1021/ja980039s

Reference yield: 82.0%

2-(3-methyl-1,4-dioxo-1,4-dihydro-2-naphthalenyl)benzaldehyde (827347-03-5) → benz[a]anthracene-7,12-dione (2498-66-0)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; at 80 ℃; for 0.166667h; Irradiation;

DOI:10.1039/b412932f

upstream raw materials:

Perbenzoic acid

chloroform

benz[a]anthracene

7,12-Dihydrobenz[a]anthracene

Downstream raw materials:

(+/-)-7.12c-dihydroxy-7r.12t-dimethyl-7.12-dihydro-benz[a]anthracene

7-iodomethyl-12-methylbenz[a]anthracene

7,12-dimethyl-1,2-benzanthracene

7,12-diphenyl-7,12-dihydro-benz[a]anthracene-7,12-diol

Refernces

THE SYNTHESIS OF 5-PHENYL-9,10-DIALKYL-9,10-DIHYDROXY-9,10-DIHYDRO-l, 2-BENZANTHRACENES AND RELATED COMPOUNDS

10.1021/jo01225a005

The study focuses on the synthesis and analysis of certain benzanthracene derivatives with potential estrogenic and carcinogenic properties. The researchers synthesized various 9,10-dialkyl-9,10-dihydroxy-9,10-dihydro-1,2-benzanthracenes and related compounds, starting from 1,2-benzanthraquinone and 5-phenyl-1,2-benzanthraquinone. They used Grignard reagents, such as methylmagnesium iodide, ethylmagnesium bromide, and n-propylmagnesium bromide, to introduce different alkyl groups into the benzanthracene structure. The synthesized compounds were then tested for their ability to induce oestrus in ovarietomized mice, revealing that some of them, particularly those with ethyl and n-propyl groups, exhibited significant estrogenic activity. Additionally, the study explored the relationship between chemical structure and both estrogenic and carcinogenic properties, aiming to understand how modifications to the benzanthracene core affect these biological activities.

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