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
• Article Data: 12

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

Chemical Properties

WHITE CRYSTALLINE POWDER

Uses

1,2,4-tribromobenzene is used in the synthesis of hyper branched poly(p-phenylene ethynylenes). It is used as 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. It is a compound commonly used in organic synthesis reactions.

General Description

1,2,4-tribromobenzene on photochemical dehalogenation in open-air solutions of acetonitrile yields 1,4-dibromobenzene, 1,3-dibromobenzene and 1,2-dibromobenzene.

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

• 106-37-6 1.4-dibromobenzene 
• 2113-57-7 3-bromobiphenyl 
• 55048-28-7 4,4',4''-benzene-1,2,4-triyl-tris-morpholine 
• 51100-94-8 4-(3-morpholinophenyl)morpholine 
• 626-39-1 1,3,5-trisbromobenzene 
• 615-55-4 3,4-dibromoaniline 
• 89365-48-0 1,2,4-tribromo-5-nitrobenzene 
• 275-51-4 azulene 
• 134646-03-0 1,4-dibromo-2-(methylthio)benzene 
• 861882-69-1 t-butyl 2,5-dibromobenzoate 
• 1094602-68-2 1,2,4-tris-(9'-phenanthryl)benzene 
• 1428470-61-4 1,2,4-tris(1-imidazolyl)benzene 
• 7641-80-7 1,2,4-Trivinyl-benzol 
• 1165-53-3 1,2,4-triphenylbenzene 

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

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.

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.