1-Bromo-2-iodobenzene

Base Information

• Chemical Name: 1-Bromo-2-iodobenzene
• CAS No.: 583-55-1
• Molecular Formula: C6H4BrI
• Molecular Weight: 282.906
• Hs Code.: 29049090
• European Community (EC) Number: 209-508-9
• DSSTox Substance ID: DTXSID1060394
• Nikkaji Number: J94.973F
• Wikidata: Q72457471
• Mol file: 583-55-1.mol

Synonyms:1-Iodo-2-bromobenzene;2-Bromo-1-iodobenzene;2-Bromoiodobenzene;2-Iodobromobenzene;o-Bromophenyl iodide;o-Iodobromobenzene;

Chemical Property of 1-Bromo-2-iodobenzene

Chemical Property:

• Appearance/Colour: light yellow to red liquid
• Vapor Pressure: 0.0357mmHg at 25°C
• Melting Point: 9-10 °C(lit.)
• Refractive Index: n20/D 1.661(lit.)
• Boiling Point: 249.7 °C at 760 mmHg
• Flash Point: 104.8 °C
• PSA: 0.00000
• Density: 2.203 g/cm³
• LogP: 3.05370
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Light Sensitive
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• Water Solubility.: Not miscible or difficult to mix in water.
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 281.85411
• Heavy Atom Count: 8
• Complexity: 74.9

Purity/Quality:

99% ^*data from raw suppliers

1-Bromo-2-iodobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Monoaromatics
• Canonical SMILES: C1=CC=C(C(=C1)Br)I
• Uses: suzuki reaction 2-Bromoiodobenzene is used in the synthesis of diarylamines.

Technology Process of 1-Bromo-2-iodobenzene

There total 23 articles about 1-Bromo-2-iodobenzene 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: 95.0%

2-bromobenzoic-acid (88-65-3) → 1-Bromo-2-iodobenzene (583-55-1)

Guidance literature:

With 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione; In 1,2-dichloro-ethane; for 15h; Irradiation; Inert atmosphere; Reflux;

DOI:10.1002/adsc.201100145

Reference yield: 90.0%

bromobenzene (108-86-1,52753-63-6) → 1-Bromo-2-iodobenzene (583-55-1) + 1,4-bromoiodobenzene (589-87-7)

Guidance literature:

With iodine; fluorine; In chloroform; trichlorofluoromethane; at -20 ℃; for 0.5h;

DOI:10.1021/jo00298a032

Reference yield: 89.0%

bis-[(trifluoroacetoxy)iodo]benzene (2712-78-9) → 1-Bromo-2-iodobenzene (583-55-1) + 1,4-bromoiodobenzene (589-87-7)

Guidance literature:

With bromine; In chloroform; Ambient temperature;

upstream raw materials:

2-bromoaniline

1-iodo-2-(trimethylsilyl)benzene

bromobenzene

iodobenzene

Downstream raw materials:

10-(2-bromophenyl)-10H-phenoxazine

1,2-bis(dimethylsilyl)benzene

o-bromobenzophenone

2-methylphenyl bromide

Refernces

An efficient intermolecular [Pd]-catalyzed C-C and intramolecular [Cu]-catalyzed C-O bonds formation: Synthesis of functionalized flavans and benzoxepine

10.1016/j.tetlet.2012.05.050

The research focuses on the development of an efficient three-step strategy for the synthesis of functionalized flavans and benzoxepine, starting from readily available 2-bromoiodobenzenes and aryl vinyl alcohols. The purpose of this study is to employ intermolecular [Pd]-catalyzed C–C and intramolecular [Cu]-catalyzed C–O bond formations as key transformations in the synthesis process. The researchers successfully extended this method to benzoxepine and demonstrated its efficiency through the synthesis of a number of analogs. The chemicals used in this process include 2-bromoiodobenzenes, aryl vinyl alcohols, Pd(OAc)2 as a catalyst, Et3N as a base, NaBH4 for reduction, and CuI/2,2-bipyridyl with KOtBu as the catalyst system for the cyclization step. The conclusions drawn from the research indicate that this strategy is efficient and amenable for the synthesis of a variety of flavan and benzoxepine analogs, with further investigations ongoing for other benzoxepine analogs and potential total synthesis of flavonoid natural products.