1,4-Dibromo-2,5-diiodobenzene

Base Information

• Chemical Name: 1,4-Dibromo-2,5-diiodobenzene
• CAS No.: 63262-06-6
• Molecular Formula: C6H2Br2I2
• Molecular Weight: 487.699
• Hs Code.: 2903999090
• European Community (EC) Number: 679-883-5
• DSSTox Substance ID: DTXSID30456011
• Nikkaji Number: J1.758.406E
• Wikidata: Q72464178
• Mol file: 63262-06-6.mol

Synonyms:1,4-Dibromo-2,5-diiodobenzene;63262-06-6;Benzene, 1,4-dibromo-2,5-diiodo-;MFCD00082898;SCHEMBL733492;AMY053;DTXSID30456011;IVKPEQAIHJWGGT-UHFFFAOYSA-N;1, 4-dibromo-2,5-diiodobenzene;1,4-di-bromo-2,5-diiodobenzene;BCP19592;CK2360;ZB0608;AKOS015995461;AB03145;GS-5474;SY041736;CS-0099451;D3904;FT-0718900;A856500

Chemical Property of 1,4-Dibromo-2,5-diiodobenzene

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 163-165oC
• Boiling Point: 377.174oC at 760 mmHg
• Flash Point: 181.909oC
• PSA: 0.00000
• Density: 2.939g/cm3
• LogP: 4.42080
• Storage Temp.: 2-8°C(protect from light)
• Sensitive.: Light Sensitive
• Solubility.: soluble in Toluene
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 487.65922
• Heavy Atom Count: 10
• Complexity: 106

Purity/Quality:

98% ^*data from raw suppliers

1,4-Dibromo-2,5-diiodobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=CC(=C1I)Br)I)Br
• Uses: 1,4-Dibromo-2,5-diiodobenzene is a useful synthetic intermediate in the synthesis of Benzo[1,2-b:4,5-b'']dithiophene (B200100); a reagent in the synthesis of high-crystalline medium-band-gap polymers used for organic photovoltaic cells. Benzo[1,2-b:4,5-b'']dithiophene is also a precursor in the preparation of benzodithiophene derivatives which are useful as hole injection material, hole transport material, or fluorescent material in organic electroluminescence devices.

Technology Process of 1,4-Dibromo-2,5-diiodobenzene

There total 3 articles about 1,4-Dibromo-2,5-diiodobenzene 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: 84.0%

1.4-dibromobenzene (106-37-6) → 1,4-dibromo-2,5-diiodobenzene (63262-06-6)

Guidance literature:

With sulfuric acid; iodine; at 125 - 135 ℃; for 48h; Inert atmosphere;

DOI:10.1021/ol901938f

Reference yield: 83.3%

2,5-dibromo-4-iodoaniline → 1,4-dibromo-2,5-diiodobenzene (63262-06-6)

Guidance literature:

2,5-dibromo-4-iodoaniline; With sulfuric acid; acetic acid; sodium nitrite; In water; at 0 - 50 ℃; for 1h;

With potassium iodide; In water; at 20 - 25 ℃; for 2h;

Reference yield:

1,4-dibromo-2-nitrobenzene (3460-18-2) → 1,4-dibromo-2,5-diiodobenzene (63262-06-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: iron; acetic acid / water / 3 h / 50 °C / pH 4 - 5

2.1: N-iodo-succinimide / dimethyl sulfoxide / 2 h / 20 - 30 °C

3.1: sodium nitrite; sulfuric acid; acetic acid / water / 1 h / 0 - 50 °C

3.2: 2 h / 20 - 25 °C

With N-iodo-succinimide; sulfuric acid; iron; acetic acid; sodium nitrite; In water; dimethyl sulfoxide;

upstream raw materials:

1.4-dibromobenzene

1,4-dibromo-2-nitrobenzene

Downstream raw materials:

1,4-dibromo-2-iodo-benzene

4,4''-dichloro-1,1':4',1''-terphenyl

1,4-dibromo-2,5-bis[2-(triisopropylsilyl)ethynyl]benzene

1,4-dibromo-2,5-bis{[2-(ethoxydimethylsilyl)phenyl]ethynyl}benzene

Refernces

• 1、 Chung, Lai-Hon,Feng, Zihao,He, Jun,Hu, Jieying,Li, Jian-Rong,Liao, Wei-Ming,Luo, Qian-Ru,Wu, Can-Min,Zhang, Hu,Zhong, Yuan-Hui. "Flexible side arms of ditopic linker as effective tools to boost proton conductivity of Ni8-pyrazolate metal-organic framework". supporting information. . Retrieved 2022/01/11.
• 2、 Hendrich, Christoph M.,Hannibal, Valentin D.,Eberle, Lukas,Hertwig, Leif E.,Zschieschang, Ute,Rominger, Frank,Rudolph, Matthias,Klauk, Hagen,K. Hashmi, A. Stephen. "Gold-Catalyzed Synthesis of π-Extended Carbazole-Based Systems and their Application as Organic Semiconductors". supporting information. p. 1401 - 1407. Retrieved 2021/02/03.