2,9-dibromo-1,10-phenanthroline-5,6-dione

Base Information

• Chemical Name: 2,9-dibromo-1,10-phenanthroline-5,6-dione
• CAS No.: 943861-95-8
• Molecular Formula: C₁₂H₄Br₂N₂O₂
• Molecular Weight: 367.984
• Mol file: 943861-95-8.mol

Synonyms:2,9-dibromo-4a,6a-dihydro-1,10-phenanthroline-5,6-dione

Chemical Property of 2,9-dibromo-1,10-phenanthroline-5,6-dione

Chemical Property:

• Boiling Point: 574.3±50.0 °C(Predicted)
• PKA: -4.68±0.20(Predicted)
• Density: 2.068±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

2,9-Dibromo-1,10-phenanthroline-5,6-dione 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,9-dibromo-1,10-phenanthroline-5,6-dione

There total 4 articles about 2,9-dibromo-1,10-phenanthroline-5,6-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: 80.5%

2,9-dibromo-1,10-phenanthroline (39069-02-8) → 2,9-dibromo-4a,6a-dihydro-1,10-phenanthroline-5,6-dione (943861-95-8)

Guidance literature:

With sulfuric acid; nitric acid; potassium bromide; at 0 - 80 ℃; for 3.5h;

DOI:10.1002/anie.202003251

Reference yield:

1,10-Phenanthroline (66-71-7) → 2,9-dibromo-4a,6a-dihydro-1,10-phenanthroline-5,6-dione (943861-95-8)

Guidance literature:

Multi-step reaction with 2 steps

1: phosphorus tribromide / nitrobenzene / 5.5 h / 170 °C

2: potassium bromide; sulfuric acid; nitric acid / 3.5 h / 0 - 80 °C

With sulfuric acid; nitric acid; phosphorus tribromide; potassium bromide; In nitrobenzene;

DOI:10.1002/anie.202003251

Reference yield:

6,7-dihydro-5H-[1,4]diazepino[1,2,3,4-l,m,n][1,10]phenanthroline-4,8-diium dibromide (15302-99-5) → 2,9-dibromo-4a,6a-dihydro-1,10-phenanthroline-5,6-dione (943861-95-8)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium hexacyanoferrate(III); sodium hydroxide / water / 4 h / 20 °C / Inert atmosphere; Schlenk technique

2: phosphorus tribromide; phosphorus(V) oxybromide / 18 h / 192 °C / Inert atmosphere; Schlenk technique

3: potassium bromide; sulfuric acid; nitric acid / 4 h / 80 °C / Inert atmosphere; Schlenk technique

With sulfuric acid; nitric acid; phosphorus tribromide; potassium bromide; sodium hydroxide; potassium hexacyanoferrate(III); phosphorus(V) oxybromide; In water;

DOI:10.1002/ejic.202100290

upstream raw materials:

2,9-dibromo-1,10-phenanthroline

1,10-Phenanthroline

6,7-dihydro-5H-[1,4]diazepino[1,2,3,4-l,m,n][1,10]phenanthroline-4,8-diium dibromide

3,6,7,9-tetrahydro-5H-<1,4>diazepino<1,2,3,4-lmn><1,10>phenanthroline-3,9-dione

Downstream raw materials:

2,9-bis(4-octyloxyphenyl)-1,10-phenanthroline-5,6-dione

2,9-bis(4-butylphenyl)-1,10-phenanthroline-5,6-dione

2,9-bis[4-(diphenylamino)phenyl]-1,10-phenanthroline-5,6-dione

Refernces

• 1、 Chen, Kai-Kai,Guo, Song,Li, Xiyou,Liu, Heyuan,Lu, Tong-Bu,Zhang, Zhi-Ming. "Strong Visible-Light-Absorbing Cuprous Sensitizers for Dramatically Boosting Photocatalysis". supporting information. p. 12951 - 12957. Retrieved 2020/05/29.
• 2、 Ishi-I, Tsutomu,Hirashima, Ryoichi,Tsutsumi, Naotaka,Amemori, Shogo,Matsuki, Shigeki,Teshima, Yuuki,Kuwahara, Rempei,Mataka, Shuntaro. "Expanded π-electron systems, tri(phenanthro)hexaazatriphenylenes and tri(phenanthrolino)hexaazatriphenylenes, that are self-assembled to form one-dimensional aggregates". experimental part. p. 6858 - 6868. Retrieved 2010/11/24.