589-87-7 Usage
Description
1-Bromo-4-iodobenzene is an organic compound with the chemical formula C6H4BrI, featuring a bromine atom at the 1st position and an iodine atom at the 4th position on a benzene ring. It is a white to brown crystalline powder, crystals, or needles, and its vapor pressure as a function of temperature has been studied using a diaphragm manometer and torsion mass-loss effusion.
Uses
1. Organic Synthesis:
1-Bromo-4-iodobenzene is used as a reagent for organic synthesis, serving as a key intermediate in the production of various organic compounds.
2. Copper-Free Sonogashira Coupling Reaction:
In the field of organic chemistry, 1-Bromo-4-iodobenzene is used as a substrate for the copper-free Sonogashira coupling reaction in aqueous acetone. This reaction is a cross-coupling reaction between a terminal alkyne and an aryl or vinyl halide, leading to the formation of a carbon-carbon bond.
3. Synthesis of β,β-Dibromostyrene:
1-Bromo-4-iodobenzene is employed as a starting reagent in the synthesis of β,β-dibromostyrene, which is an important intermediate in the production of various chemical compounds.
4. Suzuki Reaction:
In the field of medicinal chemistry, 1-Bromo-4-iodobenzene has been used in Suzuki reactions, which are palladium-catalyzed cross-coupling reactions between an organoboron compound and an organic halide or triflate. These reactions are widely used in the synthesis of complex organic molecules, including pharmaceuticals and natural products.
5. In Situ Desilylation and Coupling of Silylated Alkynes:
1-Bromo-4-iodobenzene is utilized as a reagent for in situ desilylation and coupling of silylated alkynes, which is a crucial step in the synthesis of various organic compounds, particularly in the field of pharmaceuticals.
6. Total Syntheses of Ent-Conduramine A and Ent-7-Deoxypancratistatin:
In the total syntheses of ent-conduramine A and ent-7-deoxypancratistatin (alkaloids), 1-Bromo-4-iodobenzene serves as a starting reagent, playing a vital role in the development of these complex organic molecules with potential biological activities.
Synthesis methods
Industrial parabromoaniline is as raw material, by diazotization, iodo-synthesis of bromo iodobenzene. Preferred synthesis conditions: firstly 0.02mol parabromoaniline is dissolved in a mass fraction of 20% sulfuric acid medium, then reacts with 0.021molNaNO2 to generate bromophenyl diazonium sulfate at-10℃, and then chloroform and 0.021molKI is added into solution to process iodination reaction, after simple treatment bromo-iodobenzene crude product (which the bromo-iodobenzene HPLC purity 98.4%) is obtained, total yield after purification is 80%, increases by 15% than before improved. The product processes structural characterization by IR and 1HNMR. The improved method can greatly improve the purity of the crude product, this avoids the trouble of going through the column, this method is safe and easy to operate, easy to control the process, cost is lower, it is more suitable for the preparation of 1-Bromo-4-iodobenzene.
Unit: Heilongjiang University of Chemistry and Materials Science
Author: Guo Jing Bai Xuefeng Lvhong Fei
Check Digit Verification of cas no
The CAS Registry Mumber 589-87-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 9 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 589-87:
(5*5)+(4*8)+(3*9)+(2*8)+(1*7)=107
107 % 10 = 7
So 589-87-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H4BrI/c7-5-1-3-6(8)4-2-5/h1-4H
589-87-7Relevant articles and documents
Acidic ionic liquid supported on silica-coated magnetite nanoparticles as a green catalyst for one-pot diazotization-halogenation of the aromatic amines
Isaad, Jalal
, p. 49333 - 49341 (2014)
Acidic ionic liquid was immobilized on silica-coated magnetite nanoparticles (Fe3O4@SILnP) and used as an efficient heterogeneous catalyst for the diazotization-iodination reaction of different aromatic amines under solvent-free conditions at room temperature. The diazonium salts that are formed by this catalyst are stable at room temperature and react rapidly with sodium iodide to produce aryl iodides in good to excellent yields. This method has some advantages such as low pollution, rapid access to products, simple work-up and easy separation of catalyst from the reaction mixture.
Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange
Boehm, Philip,Cacherat, Bastien,Lee, Yong Ho,Martini, Tristano,Morandi, Bill
supporting information, p. 17211 - 17217 (2021/07/02)
We report an efficient and broadly applicable palladium-catalyzed iodination of inexpensive and abundant aryl and vinyl carboxylic acids via in situ activation to the acid chloride and formation of a phosphonium salt. The use of 1-iodobutane as iodide source in combination with a base and a deoxychlorinating reagent gives access to a wide range of aryl and vinyl iodides under Pd/Xantphos catalysis, including complex drug-like scaffolds. Stoichiometric experiments and kinetic analysis suggest a unique mechanism involving C?P reductive elimination to form the Xantphos phosphonium chloride, which subsequently initiates an unusual halogen exchange by outer sphere nucleophilic substitution.
Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations
Deckers, Kristina,Fricke, Christoph,Schoenebeck, Franziska
supporting information, p. 18717 - 18722 (2020/08/25)
While halogenation is of key importance in synthesis and radioimaging, the currently available repertoire is largely designed to introduce a single halogen per molecule. This report makes the selective introduction of several different halogens accessible. Showcased here is the privileged stability of nontoxic aryl germanes under harsh fluorination conditions (that allow selective fluorination in their presence), while displaying superior reactivity and functional-group tolerance in electrophilic iodinations and brominations, outcompeting silanes or boronic esters under rapid and additive-free conditions. Mechanistic experiments and computational studies suggest a concerted electrophilic aromatic substitution as the underlying mechanism.