1,8-Dibromoanthraquinone

Base Information

• Chemical Name: 1,8-Dibromoanthraquinone
• CAS No.: 38313-16-5
• Molecular Formula: C14H6Br2O2
• Molecular Weight: 366.008
• DSSTox Substance ID: DTXSID20398496
• Nikkaji Number: J89.225D
• Wikidata: Q82200507
• Mol file: 38313-16-5.mol

Synonyms:1,8-dibromoanthraquinone;38313-16-5;1,8-dibromoanthracene-9,10-dione;1,8-Dibromo-9,10-anthraquinone;9,10-Anthracenedione, 1,8-dibromo-;SCHEMBL5412322;DTXSID20398496;QIFCTRBXWWHIFG-UHFFFAOYSA-N;1,8-dibromo-9,10-Anthracenedione

Chemical Property of 1,8-Dibromoanthraquinone

Chemical Property:

• Melting Point: 152-154 °C(Solv: nitrobenzene (98-95-3))
• Boiling Point: 491.8±45.0 °C(Predicted)
• PSA: 34.14000
• Density: 1.911±0.06 g/cm3(Predicted)
• LogP: 3.98700
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 365.87141
• Heavy Atom Count: 18
• Complexity: 350

Purity/Quality:

1,8-dibromo-9,10-Anthracenedione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)Br)C(=O)C3=C(C2=O)C=CC=C3Br
• Uses: 1,8-dibromo-9,10-Anthracenedione is commonly used in electron-transfer reactions, and has been used as a reactant in the synthesis of ferrocene-quinone conjugated oligomers and polymers.

Technology Process of 1,8-Dibromoanthraquinone

There total 8 articles about 1,8-Dibromoanthraquinone 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: 67.0%

1,8-dichloroanthraquinone (82-43-9) → 1,8-dibromoanthraquinone (38313-16-5)

Guidance literature:

With phosphoric acid; potassium bromide; copper dichloride; In nitrobenzene; for 48h; Reflux;

DOI:10.1039/c9dt03238j

Reference yield:

1,8-anthraquinonedisulphonic acid (82-48-4) → 1,8-dibromoanthraquinone (38313-16-5)

Guidance literature:

With water; bromine; at 240 ℃; im Rohr;

Reference yield:

9,10-phenanthrenequinone (84-65-1) → 1,8-dibromoanthraquinone (38313-16-5)

Guidance literature:

Multi-step reaction with 2 steps

1: mercury oxide / Darst;bei der Sulfurierung

2: water; bromine / 240 °C / im Rohr

With water; bromine; mercury(II) oxide;

upstream raw materials:

1,8-anthraquinonedisulphonic acid

1,8-diamino-anthraquinone

1,8-dichloroanthraquinone

1,5-anthraquinone disulfonate

Downstream raw materials:

1,8-BrAmAq

1,8-Am₂Aq

1,8-Dibrom-9-phenylanthracen

1,8-dibromoanthraquinone

Refernces

• 1、 Yamashita, Makoto,Watanabe, Kentaro,Yamamoto, Yohsuke,Akiba, Kin-ya. "Synthesis of a new tridentate anthracene ligand bearing (i-Pr)2P group at 1,8-positions: Facile bond switch on tetracoordinate boron atom". . p. 1104 - 1105. Retrieved 2001.
• 2、 Teerasarunyanon, Ratanakorn,Wilkins, Lewis C.,Park, Gyeongjin,Gabba?, Fran?ois P.. "Synthesis, structure and anion binding properties of 1,8-bis(dimesitylboryl)anthracene and its monoborylated analog". . p. 14777 - 14782. Retrieved 2019/10/16.
• 3、 Yamashita, Makoto,Yamamoto, Yohsuke,Akiba, Kin-Ya,Hashizume, Daisuke,Iwasaki, Fujiko,Takagi, Nozomi,Nagase, Shigeru. "Syntheses and structures of hypervalent pentacoordinate carbon and boron compounds bearing an anthracene skeleton - Elucidation of hypervalent interaction based on X-ray analysis and DFT calculation". . p. 4354 - 4371. Retrieved 2007/10/03.