2,3-bis(bromomethyl)-1,4-dimethoxyanthracene-9,10-dione

Base Information

• Chemical Name: 2,3-bis(bromomethyl)-1,4-dimethoxyanthracene-9,10-dione
• CAS No.: 67122-25-2
• Molecular Formula: C₁₈H₁₄Br₂O₄
• Molecular Weight: 454.115
• Mol file: 67122-25-2.mol

Synonyms:1,4-Dimethoxy-2,3-bis(bromomethyl)anthraquinone;NSC 333501

Chemical Property of 2,3-bis(bromomethyl)-1,4-dimethoxyanthracene-9,10-dione

Chemical Property:

• Vapor Pressure: 3.04E-14mmHg at 25°C
• Boiling Point: 597.6°Cat760mmHg
• Flash Point: 315.2°C
• Density: 1.706g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 2,3-Bis(bromomethyl)-1,4-dimethoxyanthracene-9,10-dione (also known as 1,4-Dimethoxy-2,3-bis(bromomethyl)anthraquinone or NSC 333501) is a functionalized anthraquinone derivative that exhibits fluorescence properties, which can be dynamically quenched by silver nanoparticles (Ag NPs) through a F?rster resonance energy transfer (FRET) mechanism. The quenching efficiency depends on the size of the Ag NPs, with larger nanoparticles leading to greater fluorescence suppression. Additionally, 2,3-bis(bromomethyl)-1,4-dimethoxyanthracene-9,10-dione serves as a reactive precursor in the synthesis of fullerene derivatives, such as dimethoxy-anthraquinone-C₆₀, which can further coordinate with transition metal complexes like [Ru(PPh₃)₂(NO)Cl]. Its electrochemical behavior, when incorporated into fullerene adducts, suggests potential stabilization of cationic species, distinguishing it from simpler anthraquinone analogs.

Technology Process of 2,3-bis(bromomethyl)-1,4-dimethoxyanthracene-9,10-dione

There total 2 articles about 2,3-bis(bromomethyl)-1,4-dimethoxyanthracene-9,10-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: 98.0%

1,4-dimethoxy-2,3-dimethylanthracene-9,10-dione (67122-24-1) → 1,4-dimethoxy-2,3-bis(bromomethyl)-anthraquinone (67122-25-2)

Guidance literature:

With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; In tetrachloromethane; for 4h; Heating;

DOI:10.1021/jo00342a005

Reference yield:

→ 1,4-dimethoxy-2,3-bis(bromomethyl)-anthraquinone (67122-25-2)

Guidance literature:

DOI:10.1021/ja00479a076

Reference yield:

1,4-dimethoxy-2,3-bis(bromomethyl)-anthraquinone (67122-25-2) → 1,4-dimethoxy-2,3-bis(toluene-4-sulfonylmethyl)anthraquinone

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / lithium chloride / tetrahydrofuran / 48 h / 20 °C

2: 73 percent / dimethylsulfoxide / 0.17 h

With lithium chloride; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.3390/10010289

upstream raw materials:

1,4-dimethoxy-2,3-dimethylanthracene-9,10-dione