583-55-1

Basic information

• Product Name: 1-Bromo-2-iodobenzene
• Synonyms: 1-bromo-2-iodo-benzen;1-Bromo-2-iodobenzene,stabilizedwithcopper;Benzene, 1-bromo-2-iodo-;-Bromo-2-iodobenzene;O-BROMOIODOBENZENE;2-BROMOIODOBENZENE;2-IODOBROMOBENZENE;1-BROMO-2-IODOBENZENE
• CAS NO: 583-55-1
• Molecular Formula: C₆H₄BrI
• Molecular Weight: 282.9
• EINECS: 209-508-9
• Product Categories: Miscellaneous;Benzene derivates;Bromine Compounds;Iodine Compounds;Aryl;C6;Halogenated Hydrocarbons;alkyl Iodine| alkyl bromide
• Mol File: 583-55-1.mol

Chemical Properties

• Melting Point: 9-10 °C(lit.)
• Boiling Point: 120-121 °C15 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow/Liquid
• Density: 2.203 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0357mmHg at 25°C
• Refractive Index: n20/D 1.661(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• Water Solubility: Not miscible or difficult to mix in water.
• Sensitive: Light Sensitive
• BRN: 1855309
• CAS DataBase Reference: 1-Bromo-2-iodobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromo-2-iodobenzene(583-55-1)
• EPA Substance Registry System: 1-Bromo-2-iodobenzene(583-55-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37-37/39
• WGK Germany: 3
• TSCA: T
• HazardClass: IRRITANT, LIGHT SENSITIVE
• Hazardous Substances Data: 583-55-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 583-55-1 differently. You can refer to the following data:
1. suzuki reaction
2. 2-Bromoiodobenzene is used in the synthesis of diarylamines.

InChI:InChI=1/C6H4BrI/c7-5-3-1-2-4-6(5)8/h1-4H

Upstream product

• 615-36-1 2-bromoaniline 
• 22424-65-3 1-iodo-2-(trimethylsilyl)benzene 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 2712-78-9 bis-[(trifluoroacetoxy)iodo]benzene 
• 108-95-2 phenol 
• 19260-00-5 o-bromodibenzoyl peroxide 
• 583-53-9 2,3-dibromobenzene 
• 100-39-0 benzyl bromide 
• 7553-56-2 iodine 
• 17151-09-6 1,2-bis(trimethylsilyl)benzene 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 88-65-3 2-bromobenzoic-acid 
• 71-43-2 benzene 

Downstream Products

• 131013-62-2 10-(2-bromophenyl)-10H-phenoxazine 
• 17613-47-7 2-bromo-2′-nitro-1,1′-biphenyl 
• 863305-32-2 diphenic acid 
• 69200-16-4 2'-bromo-[1,1'-biphenyl]-2-carboxylic acid 
• 217-59-4 triphenylene 
• 42918-20-7 1-allyl-2-bromobenzene 
• 21375-88-2 1-bromo-2-(phenylethenyl)benzene 
• 501-65-5 diphenyl acetylene 
• 120041-69-2 1-Isopropenyl-2-(2-methyl-allyl)-benzene 
• 120041-72-7 1-Cyclopent-1-enyl-2-(2-methyl-allyl)-benzene 
• 38399-13-2 2,2'-dibromotolane 
• 120093-88-1 C₁₁H₁₅BrMgSi 
• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 

Relevant articles and documents

Preparation method 2 - bromoiodobenzene

The invention discloses a preparation method of 2 -bromoiodobenzene, which comprises the following steps: under the protection of inert gas, adding triphenylphosphine to an organic solvent, adding organic amine to 50 - 75 °C DEG C under stirring conditions, and stirring 1 - 2 hours. Then iodine is added to 60 - 80 °C thermal insulation stirring 2 - 4.5 hours. Finally 2 - bromophenol was added and stirred 5 - 10 hours under reflux. The resulting reaction solution was naturally cooled to ≤ 40 °C, sodium methoxide was added, stirred and filtered, and the filtrate was post-treated to give 2 - bromoiodobenzene. 2 - Bromoiodobenzene is prepared by the method disclosed by the invention, and has the characteristics of simple process and high product yield.

Mechanism of Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen: Development of a base-catalyzed iododeboronation for radiolabeling applications

An investigation into the mechanism of Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen reagents is reported. Evidence is provided to show that this takes place via a boronate-driven ipso-substitution pathway and that Cu is not required for these processes to operate: General Lewis base catalysis is operational. This in turn allows the rational development of a general, simple, and effective base-catalyzed halodeboronation that is amenable to the preparation of 125I-labeled products for SPECT applications.

Metathesis-active ligands enable a catalytic functional group metathesis between aroyl chlorides and aryl iodides

Current methods for functional group interconversion have, for the most part, relied on relatively strong driving forces which often require highly reactive reagents to generate irreversibly a desired product in high yield and selectivity. These approaches generally prevent the use of the same catalytic strategy to perform the reverse reaction. Here we describe a catalytic functional group metathesis approach to interconvert, under CO-free conditions, two synthetically important classes of electrophiles that are often employed in the preparation of pharmaceuticals and agrochemicals—aroyl chlorides (ArCOCl) and aryl iodides (ArI). Our reaction design relies on the implementation of a key reversible ligand C–P bond cleavage event, which enables a non-innocent, metathesis-active phosphine ligand to mediate a rapid aryl group transfer between the two different electrophiles. Beyond enabling a practical and safer approach to the interconversion of ArCOCl and ArI, this type of ligand non-innocence provides a blueprint for the development of a broad range of functional group metathesis reactions employing synthetically relevant aryl electrophiles.

Visible-Light-Induced Decarboxylative Iodination of Aromatic Carboxylic Acids

A convenient, efficient and practical visible-light-induced decarboxylative iodination of aromatic carboxylic acids has been developed, and the corresponding aryl iodides were obtained in good yields. The method shows some advantages including the use of readily available aromatic carboxylic acids as the starting materials, simple and mild conditions, high efficiency, wide substrate scope and tolerance of various functional groups.

Copper-Free Double Silylation of 1,2-Dibromobenzenes Using a Mg/LiCl/DMI System

The reaction of 1,2-dibromobenzenes with chlorotrimethylsilane efficiently proceeded in the presence of Mg and LiCl in DMI under mild conditions, giving 1,2-bis(trimethylsilyl)benzenes in good to high yields. The reaction of 1,2-dibromobenzenes with chlorodimethylsilane under the same conditions afforded the corresponding 1,2-bis(dimethylsilyl)benzenes in high yields. Functional group transformations of 1,2-bis(trimethylsilyl)benzene were conducted to demonstrate the synthetic utility.

LIGHT-EMITTING MATERIAL FOR ORGANIC ELECTROLUMINESCENT DEVICE, ORGANIC ELECTROLUMINESCENT DEVICE USING SAME, AND MATERIAL FOR ORGANIC ELECTROLUMINESCENT DEVICE

Disclosed are a novel aromatic compound having excellent light emitting efficiency and thermal stability, a manufacturing method thereof, and an organic electroluminescent device comprising the novel aromatic compound. According to the present invention, provided are an aromatic compound forming a ring, and a novel aromatic derivative represented by chemical formula 1, which improves performance of a device. In the chemical formula 1, Z is equally or differently N (nitrogen), O (oxygen), or S (sulfur) in each case. Also, when Z is N (nitrogen), L1 is an integer of 1, and when Z is O (oxygen) or S (sulfur), L1 is an integer of 0.COPYRIGHT KIPO 2015

A practical and general ipso iodination of arylboronic acids using N-iodomorpholinium iodide (NIMI) as a novel iodinating agent: mild and regioselective synthesis of aryliodides

A mild and efficient protocol for the ipso-iodination of aryl boronic acids using N-iodomorpholinium iodide (NIMI) generated in situ from morpholine and molecular iodine as a novel iodinating agent has been developed. The addition of a catalytic amount of copper iodide found to promote rate enhancement of the iodination reaction and dramatic increase in the yield depending upon the nature of the boronic acid was observed. The mechanistic study revealed that depending upon the nature of the substrate, either the classical ipso substitution or copper catalysed iododeborylation pathway overall dominates the present iodination reaction. The features such as mild reaction conditions, operational simplicity, high to excellent yields, excellent functional group compatibility and low catalyst loading make this method potentially useful in organic synthesis.

Tribromoisocyanuric acid in trifluoroacetic acid: An efficient system for smooth brominating of moderately deactivated arenes

Moderately deactivated arenes are efficiently brominated by the reaction with tribromoisocyanuric acid (0.34 mol equiv) in trifluoroacetic acid at room temperature in 48-85% isolated yield. This medium avoids the polybromination of the substrate, observed in the same reaction performed in 98% H 2SO4. Georg Thieme Verlag Stuttgart · New York.

A facile synthesis of indolo[3,2,1-jk]carbazoles via palladium-catalyzed intramolecular cyclization

A new efficient synthesis of indolo[3,2,1-jk]carbazoles by the palladium-catalyzed cyclization of N-(2-bromoaryl)carbazoles is described. The reaction involves intramolecular C-C bond formation, coupled with the cleavage of a C-X bond and a C-H bond on carbazole ring. Substitutions on N-aryl core with either electron-donating or electron-withdrawing groups are introduced, and different reaction factors for cyclization are evaluated.

Rhodium(III)-catalyzed oxidative ciH coupling of N-methoxybenzamides with aryl boronic acids: One-pot synthesis of phenanthridinones

General solution: An efficient rhodium-catalyzed dual CiH bond activation and cyclization of N-methoxybenzamides 1 with aryl boronic acids 2 (see scheme; Cp=Me5C5) provides a straightforward and general approach to the phenanthridinone structure, which occurs widely in natural products and drugs. Highly regioselective CiC and CiN bond formation under mild conditions afforded a wide range of substituted phenanthridinones 3. Copyright