102921-26-6

Basic information

• Product Name: (1,2-Dibromo-ethyl)-benzene
• CAS NO: 102921-26-6
• Molecular Weight: 263.96
• Mol File: 102921-26-6.mol
• Article Data: 159

Chemical Properties

• CAS DataBase Reference: (1,2-Dibromo-ethyl)-benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (1,2-Dibromo-ethyl)-benzene(102921-26-6)
• EPA Substance Registry System: (1,2-Dibromo-ethyl)-benzene(102921-26-6)

Safety Data

• Hazardous Substances Data: 102921-26-6(Hazardous Substances Data)

Upstream product

• 622-25-3 1-(2-chlorovinyl)benzene 
• 100-42-5 styrene 
• 128620-11-1 1-phenyl-2-bromodiazene 1-oxide 
• 67-56-1 methanol 
• 71-23-8 propan-1-ol 
• 71-36-3 butan-1-ol 
• 67-63-0 isopropyl alcohol 
• 75-65-0 tert-butyl alcohol 
• 78-92-2 iso-butanol 
• 78-83-1 2-methyl-propan-1-ol 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 536-74-3 phenylacetylene 
• 64-17-5 ethanol 

Downstream Products

• 93-52-7 (1,2-Dibromo-ethyl)-benzene 
• 93-52-7 (1,2-Dibromo-ethyl)-benzene 
• 53876-79-2 1,2-bis-benzenesulfonyl-1-phenyl-ethane 
• 100-42-5 styrene 
• 93-56-1 phenylethane 1,2-diol 
• 98-81-7 1-bromovinylbenzene 
• 35635-65-5 5-phenyl-5,6-dihydro-[1,4]dithiine-2,3-dicarbonitrile 
• 103-64-0 bromostyrene 
• 536-74-3 phenylacetylene 
• 98-86-2 acetophenone 
• 4333-75-9 1-(4-methoxyphenyl)-1-phenylethene 
• 1694-19-5 p-methoxystilbene 
• 108-86-1 bromobenzene 
• 120-12-7 anthracene 

Relevant articles and documents

-

-

-

-

Mild oxidative bromination of alkenes and alkynes with zinc bromide and lead tetraacetate

Zinc bromide and lead tetraacetate is a practical and safe source of bromine. The combined reagents are used to brominate a variety of alkenes to vicinal dibromoalkanes. Similarly, alkynes can be converted into dibromoalkenes in high yields. The reagents are also capable of tetrabromination of alkynes.

An environmentally benign synthesis of organic ammonium tribromides (OATB) and bromination of selected organic substrates by tetrabutylammonium tribromide (TBATB)

Stable crystalline organic ammonium tribromides (OATB), like Me4NBr3, Et4NBr3, Bu4NBr3, cetyltrimethylammonium tribromide, PyHBr3, can be readily synthesised from the reaction of the corresponding bromides with V2O5 and aqueous H2O2. Typically, TBATB, Bu4NBr3, brominates a variety of organic substrates rather easily under mild conditions. An activated aromatic ring is selectively brominated in the presence of an olefinic double bond.

Mild and Efficient Vicinal Dibromination of Olefins Mediated by Aqueous Ammonium Fluoride

A mild and efficient vicinal dibromination of olefins has been developed by using saturated aqueous ammonium fluoride solution as the promoter. Inexpensive and commercially available N -bromosuccinimide (NBS) was used as the brominating reagent. The corresponding vicinal dibromoalkanes could be obtained in good to excellent yields.

Reactions of selenium dihalides with vinylbenzenes

Alkoxyselenation of vinylbenzenes with selenium dihalides was accomplished for the first time. The reaction with selenium dibromide was the most efficient. Selenium dibromide reacted with vinylbenzene and 1-chloro-4-(prop-1-en-2-yl)benzene in chloroform or methylene chloride in the presence of methanol or ethanol to give the corresponding Markovnikov adducts, bis(2-alkoxy-2-phenylethyl) selenides and bis[2-alkoxy-2-(4-chlorophenyl)propyl] selenides in 82–95% yield with high regioselectivity. Bis(2-halo-2-phenylethyl) selenides can be obtained at low temperature (–60°C).

Cis-Dioxomolybdenum(VI) complexes with unsymmetric linear tetradentate ligands: Syntheses, structures and bromoperoxidase activities

Reactions of [MoO2(acetylacetonate)2], 2-((2-(2-hydroxyethylamino)ethylamino)methyl)-4-R-phenols (H2Ln, n = 1-5 for R = H, Me, OMe, Cl and Br, respectively) and KOH in 1:1:2 mole ratio in methanol afford a series of complexes having the general formula cis-[MoO2(Ln)] (1, 2, 3, 4, 5) in 81-86% yields. The complexes have been characterized using elemental analysis, spectroscopy (infrared, UV-visible, and 1H NMR, 13C NMR and 13C-DEPT NMR) and electrochemical measurements. The molecular structures of 1, 2, 3, 4 have been determined using single-crystal X-ray crystallography. In each of 1, 2, 3, 4, the ONNO-donor 6,5,5-membered fused chelate rings forming (Ln)2- and the two mutually cis oxo groups assemble a distorted octahedral N2O4 coordination sphere around the metal centre. In the crystal lattice, each of 1, 2, 3, 4 forms a one-dimensional infinite chain structure via intermolecular N-H...O hydrogen bonding interactions. In cyclic voltammograms, the diamagnetic complexes display an irreversible metal-centred reduction in the potential range -0.73 to -0.88 V (vs Ag/AgCl). The physicochemical data are consistent with a very similar gross molecular structure for all of 1, 2, 3, 4, 5. All the complexes exhibit decent bromoperoxidase activities and are also able to effectively catalyse benzoin and methyl(phenyl)sulfide oxidation reactions.

Electrochemical bromination of cyclic and acyclic enes using biphasic electrolysis

A simple method of electrochemical bromination of a series of cyclic and acyclic enes (styrene and substituted styrenes, stilbene, indene, and cyclooctene) in a biphasic water-chloroform mixture mediated by bromide/bromine redox system is reported. Aqueous 25% NaBr/H2SO4 is used as the electrolyte. Regio- and stereoselective dibromination of enes is achieved. Moderate to excellent yields of the product (83-98%) is obtained depending on the substrate. Electrolyte reuse has also been demonstrated successfully using HBr in the dibromination of styrene.

Employing Aryl-Linked Bis-mesoionic Carbenes as a Pincer-Type Platform to Access Ambient-Stable Palladium(IV) Complexes

The study of palladium(IV) species has great implications for PdII/PdIV-mediated catalysis. However, most of the PdIV complexes rapidly decompose under ambient conditions, which makes the isolation, characterization and further reactivity study very challenging. The reported ancillary ligand platforms to stabilize PdIV species are dominated by chelating N-donors such as bipyridines. In this work, we present two PdIV complexes with scarcely used C-donors as the supporting platform. The anionic aryl donor and MIC (MIC=mesoionic carbene) are combined in a [CC′C]-type pincer framework to access a series of ambient-stable PdIV tris(halido) complexes. Their synthesis, solid-state structures, stability, and reactivity are presented. To the best of our knowledge, the work presented herein reports the first isolated PdIV–MIC as well as the first PdIV carbene-based aryl pincer.

Synthesis of brominated compounds. A convenient molybdenum-catalyzed procedure inspired by the mode of action of haloperoxidases

A two-phase (CHCl3/H2O) procedure for the synthesis of halogenated compounds has recently been developed. Such procedure mimics the mode of action of the enzymes haloperoxidases which contain vanadium in their active center. We have investigated the possibility to substitute vanadium with molybdenum. The molybdenum-based reactions show some advantages over the vanadium-based ones. In fact reaction times are shorter and overall yields are larger, under similar experimental conditions, both in the reaction with double bonds as well as with aromatic rings. Moreover, with double bonds, the molybdenum catalyzed process preferentially yields bromohydrins which are valuable synthetic intermediates. On the other hand, the molybdenum-catalyzed reactions show peculiar mechanistic features which deserve further investigation.

A Mild and Efficient Sonochemical Bromination of Alkenes Using Tetrabutylammonium Tribromide

The bromination of substituted alkenes using tetrabutylammonium tribromide can be effectued under mild conditions with ultrasonic irradiation.This process gives quantitatively the corresponding vicinal dibromide in high yield. Key words: bromination, tribromide, sonication, alkenes, vicinal dibromoalkanes

-

-

Polystyrene bound dioxidovanadium(V) complexes of 2-acetylpyridine derived ligands for catalytic oxidations

Three neat complexes [VVO2(acpy-bhz)] (1) [V VO2(acpy-inh)] (2) and [VVO2(acpy- nah] (3) and the corresponding polymer-supported (PS) dioxidovanadium(V) complexes having monobasic tridentat

Kinetic study of the addition of trihalides to unsaturated compounds in ionic liquids. Evidence of a remarkable solvent effect in the reaction of ICl2-

The kinetic constants and activation parameters for the reactions of Br3- and ICl2- with some alkenes and alkynes have been determined in the ionic liquids [bmim][PF6], [emim][Tf2N], [bmim][Tf2N], [hmim][TF2N], [bm2im] [Tf2N], and [bpy][TF2N] (where emim = 1-ethyl-3-methyl-imidazolium, bmim = 1-butyl-3-methylimidazolium, hmim = 1-hexyl-3-methylimidazolium, bm2im = 1-butyl-2,3-dimethylimidazolium, bpy = butylpyridinium, PF6 = hexafluorophosphate, and Tf 2N = bis(trifluoromethylsulfonyl)imide) and in 1,2-dichloroethane. The rates of both reactions increase on going from 1,2-dichloroethane to ILs. Evidence suggests that, while the hydrogen bonding ability of the imidazolium cation is probably the main factor able to increase the rate of the addition of ICl2- to double and triple bonds, this property has no effect on the electrophilic addition of Br3- to alkenes and alkynes. Furthermore, in the case of the ICl2- reaction, the hydrogen bonding ability of ILs can be exploited to suppress the unwanted nucleophilic substitution reaction on the products by the Cl - anion.

N-bromosuccinimide and lithium bromide: An efficient combination for the dibromination of carbon-carbon unsaturated bonds

Compounds possessing unsaturated bonds such as alkenes, alkynes, allenes, and methylenecyclopropanes (MCPs) can be dibrominated within minutes by NBS and lithium bromide in THF at room temperature in good to excellent yields under mild conditions. Georg Thieme Verlag Stuttgart.

-

-

Oxidative bromination reaction using Cu2+- perfluorophthalocyanine-immobilized silica gel catalyst under mild reaction conditions

A simplified, facile route has been applied for the grafting of copper(II) perfluorophthalocyanine complex onto functionalized silica gel. The resulting organic-inorganic hybrid material is used as an efficient and recyclable catalyst for the regioselective oxidative bromination of various aromatic substrates using KBr/H2O2 as the reagents, affording high yields under mild conditions. High catalytic activity efficiency could be attributed to the heterogenization of soluble metal complexes on the high surface area host.

A Conformationally Restricted Aza-BODIPY Platform for Stimulus-Responsive Probes with Enhanced Photoacoustic Properties

Photoacoustic (PA) dyes, which absorb near-infrared (NIR) light to generate an ultrasonic signal, can be detected at centimeter depths in tissues with significantly higher resolution than dyes imaged with fluorescence-based methods. As such, PA agents show great promise as research tools for the study of live-animal disease models. However, the development of activatable PA probes has been hampered by the relative scarcity of appropriate PA-active molecular platforms with properties that can be manipulated in a rational manner. Herein we synthesized and evaluated six modifications to the aza-BODIPY dye platform with respect to their absorbance, fluorescence, and PA properties. We identified a promising conformationally restricted aza-BODIPY (CRaB) scaffold that prioritizes three criteria necessary for the design of stimulus-responsive dyes with optimal ratiometric PA response: absorbance at NIR wavelengths, strong PA intensity, and large Δλ upon interaction with the desired stimulus. Using this scaffold, we synthesized three chemically diverse stimulus-responsive PA probes and demonstrated between 2- and 8-fold improvements in theoretical ratiometric response in vitro. This suggests that improvements in PA parameters are generalizable. Finally, we validated the in vitro turnover of each CRaB PA probe and demonstrated the in vivo potential of the CRaB scaffold by direct comparison to an established hypoxia-responsive probe for the detection of tumor hypoxia.

Bromination of various unsaturated ketones and olefines with poly(4-methyl-5-vinylthiazolium) hydrotribromide

Poly(4-Methyl-5-Vinylthiazolium) Hydrotribromide (P4M5VTHT) synthesis is reported; this polymer, incorporating 45% of bromine, was found to be a stable, regenerable and a successful brominating reagent for various organic unsaturations.

A near-infrared dye based on BODIPY for tracking morphology changes in mitochondria

M-DPT, a BODIPY-based water soluble near-infrared fluorescent probe with thiophene at the 1,7-position, is synthesized. M-DPT is found to possess high specificity to mitochondria, superior photostability, and appreciable tolerance to microenvironmental changes. Thus, this probe is a highly suitable imaging agent for targeting mitochondria and tracking morphology changes.

Bromination of olefins with HBr and DMSO

A simple and inexpensive methodology is reported for the conversion of alkenes to 1,2-dibromo alkanes via oxidative bromination using HBr paired with dimethyl sulfoxide, which serves as the oxidant as well as cosolvent. The substrate scope includes 21 olefins brominated in good to excellent yields. Three of six styrene derivatives yielded bromohydrins under the reaction conditions.

-

-

Effect of cyclodextrin complexation in bromine addition to unsymmetrical olefins: Evidence for participation of cyclodextrin hydroxyl groups

Multiple recognition by cyclodextrin in a bimolecular reaction, namely bromination of styrene, methyl cinnamate, phenylacetylene and allylbenzene, has been studied. Bromohydrin is obtained as a major product along with dibromide in the bromination of styrene and methyl cinnamate. The percentage of bromohydrin decreases as the cavity size increases. With phenylacetylene, bromophenylacetylene and phenacyl bromide are obtained in addition to the dibromides. In the bromination of cyclodextrin complexes of allylbenzene, the product distribution is the same as in solution bromination. The observed results demonstrate the efficiency of cyclodextrin in stabilizing the open carbocationic intermediate and thus provide chemical evidence for the participation of cyclodextrin hydroxyl groups. The Royal Society of Chemistry 2005.

Synthesis, characterization and catalytic activity of dioxidomolybdenum(VI) complexes of tribasic pentadentate ligands

[MoVIO2(acac)2] (Hacac = acetylacetone) reacts with the tribasic pentadentate Schiff bases H3sal-dahp (I), H3clsal-dahp (II) and H3brsal-dahp (III) (sal = salicylaldehyde, clsal = 5-chlorosalicylaldehyde, brsal = 5- bromosalicylaldehyde, dahp = 1,3-diamino-2-hydroxypropane) in methanol under refluxing conditions to yield the dioxidomolybdenum(VI) complexes [Mo VIO2(Hsal-dahp)(H2O)] (1), [Mo VIO2(Hclsal-dahp)(H2O)] (2) and [Mo VIO2(Hbrsal-dahp)(H2O)] (3), respectively. In these complexes, only one set of phenolic oxygen and azomethine nitrogen atoms, along with the alcoholic oxygen atom of the ligands coordinate to the molybdenum. The reactions of these complexes with pyridine result in the formation of [MoVIO2(Hsal-dahp)(py)] (4), [Mo VIO2(Hclsal-dahp)(py)] (5) and [MoVIO 2(Hbrsal-dahp)(py)] (6). A single crystal X-ray study of [Mo VIO2(Hbrsal-dahp)(DMSO)] (3a), grown by slow evaporation of a DMSO solution of 3, confirms the non-participation of one set of phenolic oxygen and azomethine nitrogen atoms of the ligand. The reaction of a methanolic solution of the in situ generated H3clsal-dahp with [Mo VIO2(acac)2] in DMSO gave [Mo VIO2(Hclsal-hdap)(DMSO)]4[Mo8O 26]·6DMSO (7) (H2clsal-hdap = Schiff base obtained by the 1:1 condensation of 5-chlorosalicylaldehyde and 1,3-diamino-2- hydroxypropane), where the non-coordinated azomethine nitrogen hydrolyzes giving a free protonated amine group, as confirmed by a single crystal X-ray study. Complexes 1, 2 and 3 catalyze the oxidative bromination of styrene to yield 1,2-dibromo-1-phenylethane, 1-phenylethane-1,2-diol and 2-bromo-1-phenylethane- 1-ol; therefore they act as functional models of vanadium dependent haloperoxidases. It has also been demonstrated that complexes 1, 2 and 3 are catalyst precursors for the oxidation of methyl phenyl sulfide and benzoin.

Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide

Homolytic hydrobromination of terminal and internal alkynes with a commercially available solution of hydrogen bromide in acetic acid has been investigated for regio- and stereoselective synthesis of bromoalkenes. Under an aerobic atmosphere at room temperature, the reaction of ethynylarenes with a small excess of HBr efficiently gave (2-bromoethenyl)arenes with good to high E-selectivity. (Alk-1-ynyl)arenes, or internal alkynes bearing both phenyl and alkyl groups at the sp-carbons also underwent the air-initiated hydrobromination to exhibit high Z-selectivity under kinetic conditions using a half equivalent of HBr.

A General Method for the Dibromination of Vicinal sp3C-H Bonds Exploiting Weak Solvent-Substrate Noncovalent Interactions

A general procedure of 1,2-dibromination of vicinal sp3 C-H bonds of arylethanes using N-bromosuccinimide as the bromide reagent without an external initiator has been established. The modulation of the strength of the intermolecular noncovalent interactions between the solvent and arylethane ethanes, quantitatively evaluated via quantum chemical calculations, allows us to circumvent the fact that arylethane ethane cannot be dibrominated through traditional methods. The mechanism was explored by both experiments and quantum chemical calculations, revealing a radical chain with HAA process.