615-54-3

Basic information

• Product Name: 1,2,4-TRIBROMOBENZENE
• Synonyms: 1,2,4-Tribomobenzene;1,2,4-tribromo-benzen;1,2,4-TRIBROMOBENZENE;1,2,4-Tribromobenzene,95%;NSC 62440
• CAS NO: 615-54-3
• Molecular Formula: C₆H₃Br₃
• Molecular Weight: 314.8
• EINECS: 210-433-9
• Product Categories: Bromine Compounds;Aryl;C6;Halogenated Hydrocarbons;Building Blocks;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 615-54-3.mol

Chemical Properties

• Melting Point: 41-43 °C(lit.)
• Boiling Point: 275 °C
• Flash Point: >230 °F
• Appearance: white crystalline powder
• Density: 2.3515 (estimate)
• Vapor Pressure: 0.0077mmHg at 25°C
• Refractive Index: >110^o(230^oF)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water.
• BRN: 1934823
• CAS DataBase Reference: 1,2,4-TRIBROMOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4-TRIBROMOBENZENE(615-54-3)
• EPA Substance Registry System: 1,2,4-TRIBROMOBENZENE(615-54-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• RTECS: DC1956500
• TSCA: Yes
• Hazardous Substances Data: 615-54-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,2,4-Tribromobenzene is used as a starting material in the synthesis of hyper branched poly(p-phenylene ethynylenes), which are important materials in the field of optoelectronics and have potential applications in light-emitting diodes (LEDs) and solar cells.
Used in Cross-Linking Reactions:
1,2,4-Tribromobenzene is used as a cross-linking reagent during Pd-catalyzed cross-coupling of 2,5-diiodo-4-[(2-ethylhexyl)oxy]methoxybenzene and 1,4-diethynyl-2,5-bis-(octyloxy)benzene. This application is relevant in the field of materials science, where cross-linking is a crucial process for creating stable and robust materials with specific properties.
Used in Chemical Research:
1,2,4-Tribromobenzene is also used in chemical research for studying the effects of photochemical dehalogenation on various organic compounds. This research can lead to a better understanding of the reactivity and properties of brominated aromatic compounds, which can be useful in the development of new synthetic methods and applications in various industries.

InChI:InChI=1/C6H3Br3/c7-4-1-2-5(8)6(9)3-4/h1-3H

Upstream product

• 64-17-5 ethanol 
• 3638-73-1 2,5-dibromoaniline 
• 615-58-7 2,4-dibromophenol 
• 106-37-6 1.4-dibromobenzene 
• 615-57-6 2,4-dibromo-aniline 
• 615-55-4 3,4-dibromoaniline 
• 64-19-7 acetic acid 
• 103-84-4 Acetanilid 
• 71-43-2 benzene 
• 62-53-3 aniline 
• 636-28-2 1,2,4,5-tetrabromobenzene 
• 22311-25-7 1,2,3,4-tetrabromobenzene 
• 7726-95-6 bromine 
• 586-78-7 para-nitrophenyl bromide 

Downstream Products

• 73654-84-9 2,4,5-tribromo-benzenesulfonic acid 
• 68557-77-7 1,2,4-tribromo-3,5-dinitro-benzene 
• 34328-38-6 3,4-Dibrom-4'-trifluormethylbenzophenon 
• 38004-83-0 2,4,5-tribromo-benzenesulfonyl chloride 
• 21702-84-1 2,4-dibromoanisole 
• 62415-74-1 3,4-dibromoanisole 
• 95970-08-4 1,4-dibromo-2-methoxybenzene 
• 106-37-6 1.4-dibromobenzene 
• 2113-57-7 3-bromobiphenyl 
• 108-86-1 bromobenzene 
• 108-36-1 1,3-dibromobenzene 
• 71-43-2 benzene 
• 583-53-9 2,3-dibromobenzene 
• 55048-28-7 4,4',4''-benzene-1,2,4-triyl-tris-morpholine 

Relevant articles and documents

Direct C–H Carboxylation Forming Polyfunctionalized Aromatic Carboxylic Acids by Combined Br?nsted Bases

CO2 fixation into electron-deficient aromatic C–H bonds proceeds with the combined Br?nsted bases LiO-t-Bu and LiO-t-Am/CsF/18-crown-6 (t-Am = CEtMe2) under a CO2 atmosphere to afford a variety of polyfunctionalized aromat

Oxidative bromination of non-activated aromatic compounds with AlBr3/KNO3 mixture

Bromination of non-activated aromatic compounds with reaction mixture containing KNO3 and AlBr3 was studied in liquid substrates and in solvent. Aluminium bromide has three different roles in this reaction mixture. First, it is a source of bromide ions, which are essential in oxidative bromination application. Second, it acts as a catalyst, and lastly, it forms acidic environment via its hydrolysis, which is necessary for enhancement of the oxidising properties of nitrate ions. It was shown that when changing the reaction conditions, different side reactions (like nitration or Friedel–Crafts type arylation) can occur. However, it is possible to guide the reaction path and receive the desired outcome by choosing the suitable reaction conditions. In addition, it was shown that there has to be water content in this reaction mixture as the bromine formation rate depends on it, while there exists an optimal volume of water, where bromine formation is the fastest.

Bromination of aromatic compounds using an Fe2O 3/zeolite catalyst

The catalytic bromination of non-activated aromatic compounds has been achieved using an Fe2O3/zeolite catalyst system. FeBr 3 was identified as the catalytic species, formed in situ from HBr and Fe2O3. The catalyst was easy-to-handle and cost effective and could also be recycled. The reaction system was also amenable to the one-pot sequential bromination/C-C bond formation of benzene.

Brominated methanes as photoresponsive molecular storage of elemental Br2

The photochemical generation of elemental Br2 from brominated methanes is reported. Br2 was generated by the vaporization of carbon oxides and HBr through oxidative photodecomposition of brominated methanes under a 20 W low-pressure mercury lamp, wherein the amount and situations of Br2 generation were photochemically controllable. Liquid CH 2Br2 can be used not only as an organic solvent but also for the photoresponsive molecular storage of Br2, which is of great technical benefit in a variety of organic syntheses and in materials science. By taking advantage of the in situ generation of Br2 from the organic solvent itself, many organobromine compounds were synthesized in high practical yields with or without the addition of a catalyst. Herein, Br2 that was generated by the photodecomposition of CH2Br2 retained its reactivity in solution to undergo essentially the same reactions as those that were carried out with solutions of Br2 dissolved in CH 2Br2 that were prepared without photoirradiation. Furthermore, HBr, which was generated during the course of the photodecomposition of CH2Br2, was also available for the substitution of the OH group for the Br group and for the preparation of the HBr salts of amines. Furthermore, the photochemical generation of Br2 from CH2Br2 was available for the area-selective photochemical bleaching of natural colored plants, such as red rose petals, wherein Br2 that was generated photochemically from CH 2Br2 was painted onto the petal to cause radical oxidations of the chromophoric anthocyanin molecules. The generation of Br 2 from brominated methanes occurred upon photoirradiation under O2. The solutions that contained elemental Br2 were useful for the synthesis of organobromine compounds and the macroscopic photochemical bleaching of colored plants. Copyright

Two flavors of PEPPSI-IPr: Activation and diffusion control in a single NHC-ligated Pd catalyst?

Abnormal reactivity has been observed in Negishi, Suzuki-Miyaura, and Kumada-Tamao-Corriu cross-couplings in which PEPPSI-IPr (where PEPPSI stands for pyridine enhanced precatalyst preparation, stabilization, and initiation and IPr refers to the NHC ligand) is employed, implicating the presence of two distinct Pd0 species in the catalytic cycle. Polybrominated arenes and organometallic reagents react selectively to give the product of exhaustive polysubstitution regardless of the initial reaction stoichiometry. Competition experiments suggest that, after an initial activation controlled oxidative addition, reductive elimination produces an ultrareactive Pd0 species which consumes all remaining C-Br bonds in the molecule under diffusion control.

N-halosuccinimide/BF3-H2O, efficient electrophilic halogenating systems for aromatics

N-Halosuccinimides (NXS, 1) are efficiently activated in trifluoromethanesulfonic acid and BF3-H2O, allowing the halogenations of deactivated aromatics. Because BF3-H2O is more economic, easy to prepare, nonoxidizing, and offers sufficiently high acidity (-H0 ≈ 12, only slightly lower than that of trifluoromethanesulfonic acid), an efficient new electrophilic reagent combination of NXS/BF3-H2O has been developed. DFT calculations at the B3LYP/6-311++G**//B3LYP/6-31G* level suggest that protonated N-halosuccinimides undergo further protosolvation at higher acidities to reactive superelectrophilic species capable either in the transfer of X+ from the protonated forms of NXS to the aromatic substrate or in forming a highly reactive and solvated X+ which would readily react with the aromatic substrates. Structural aspects of the BF 3-H2O complex have also been investigated.

Ozone-mediated reaction of polychlorobenzenes and some related halogeno compounds with nitrogen dioxide: A novel non-acid methodology for the selective mononitration of moderately deactivated aromatic systems

In the presence of ozone and preferably methanesulfonic acid as catalyst, polychlorobenzenes undergo selective mononitration with nitrogen dioxide at low temperatures, giving the corresponding polychloronitrobenzenes, in most cases in nearly quantitative yields.

Magnetic susceptibilities of organic compounds: Part V - Influence of substituents on diamagnetic susceptibilities of disubstituted and trisubstituted benzenes

The magnetic susceptibilities of a number of triads of isomeric disubstituted benzenes have been determined, choosing the compounds in such a way that the substituents are present in the following combinations: (i) two electron-releasing substituents, (ii) a halogeno and an electron-releasing substituent, (iii) a halogeno and an electron-attracting substituent, and (iv) two halogeno substituents.The data show that for types (i), (ii) and (iv), the ortho isomers have the highest magnetic susceptibilities, the susceptibilities decreasing in the order: ortho > meta > para; for type (iii), the meta-isomers have the highest susceptibilities, the susceptibilities decreasing in the order: meta > para > ortho.The diamagnetic susceptibilities of some isomeric trisubstituted benzenes have also been determined and the data reveal that the susceptibility is the highest where the crowding of substituents is the highest (1,2,3-isomer) and lowest where the substituents are staggered and least crowded (1,3,5-isomer).Another observation made in the case of trisubstituted benzene is the applicability of a principle of additivity of their diamagnetic susceptibilities.

Synthetically Useful Aryl-Aryl Bond Formation via Grignard Generation and Trapping of Arynes. A One Step Synthesis of p-Terphenyl and Unsymmetric Biaryls

A one-pot route to p-terphenyls is described.Addition of 1,4-dibromo-2,5-diiodobenzene, 1, to excess aryl Grignard reagent gives the terphenyl di-Grignard 2 and the trihalo mono-Grignard 5.After aqueous quench, p-terphenyls are isolated in 30percent to 50percent yield (Table I).This yield can be improved to 70-80percent by adding potassium tert-butoxide or lithium tetramethylpiperidide to the reaction mixture prior to workup.Mechanisms involving organometallic aryne intermediates are proposed.With o-bromoiodoarenes in place of tetrahaloarenes the method can be adapted to prepare unsymmetric biaryls in good yield (Table II).