138526-69-9

Basic information

• Product Name: 5-Bromo-1,2,3-trifluorobenzene
• Synonyms: 5-BROMO-1,2,3-TRIFLUOROBENZENE;3,4,5-TRIFLUOROBROMOBENZENE;1-BROMO-3,4,5-TRIFLUOROBENZENE;1,2,3-TRIFLUORO-5-BROMOBENZENE;BENZENE, 5-BROMO-1,2,3-TRIFLUORO-;1-Bromo-3,4,5-trifluoribenzene;3,4,5-Trifluoro-1-bromobenzene;3,4,5-Ttrifluorobromobenzene
• CAS NO: 138526-69-9
• Molecular Formula: C₆H₂BrF₃
• Molecular Weight: 210.98
• EINECS: 418-480-9
• Product Categories: Other fluorin-contained compounds;Fluorobenzene;Aromatic Hydrocarbons (substituted) & Derivatives;Miscellaneous;Benzenes;Aryl;Aryl Fluorinated Building Blocks;Building Blocks;C6;Chemical Synthesis;Fluorinated Building Blocks;Halogenated Hydrocarbons;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks;Fluorine series
• Mol File: 138526-69-9.mol

Chemical Properties

• Melting Point: <-20°C
• Boiling Point: 47-49 °C60 mm Hg(lit.)
• Flash Point: 113 °F
• Appearance: Colorless to yellowish liquid
• Density: 1.767 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.6mmHg at 25°C
• Refractive Index: n20/D 1.482(lit.)
• Storage Temp.: Flammables area
• Solubility: 0.130g/l
• Water Solubility: insoluble
• BRN: 7249191
• CAS DataBase Reference: 5-Bromo-1,2,3-trifluorobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-1,2,3-trifluorobenzene(138526-69-9)
• EPA Substance Registry System: 5-Bromo-1,2,3-trifluorobenzene(138526-69-9)

Safety Data

• Hazard Codes: Xn,N,Xi,F
• Statements: 10-38-40-41-51/53-36/37/38
• Safety Statements: 23-26-36/37/39-61-36-16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 2
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 138526-69-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
5-Bromo-1,2,3-trifluorobenzene is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure allows it to be a valuable building block in the synthesis of complex molecules.
Used in Flow Preparation:
5-Bromo-1,2,3-trifluorobenzene is utilized as a key component in the flow preparation of 4,4,5,5-tetramethyl-2-(3,4,5-trifluorophenyl)-1,3,2-dioxaborolane, a compound with potential applications in the field of materials science and pharmaceuticals.
Used in Liquid Crystals:
As an intermediate, 5-Bromo-1,2,3-trifluorobenzene is also employed in the production of liquid crystals. Liquid crystals are widely used in display technologies, such as televisions, computer monitors, and smartphones, due to their unique optical properties.

Flammability and Explosibility

Flammable

InChI:InChI:1S/C6H2BrF3/c7-3-1-4(8)6(10)5(9)2-3/h1-2H

Upstream product

• 163733-96-8 3,4,5-trifluoro aniline 
• 17299-94-4 1,2-dibromo-3,4,5-trifluorobenzene 
• 17299-95-5 1,5-dibromo-2,3,4-trifluorobenzene 
• 34628-01-8 1,2,3-tribromo-4,5,6-trifluoro-benzene 
• 393-79-3 1,3-dichloro-2-fluoro-4-nitrobenzene 
• 122375-82-0 2-bromo-4,5,6-trifluoroaniline 
• 20098-48-0 3,4,5-trichloronitrobenzen 
• 3107-19-5 3,5-dichloro-4-fluoro-nitrobenzene 
• 2268-05-5 1,3-dichloro-2-fluorobenzene 
• 2729-34-2 3,5-dichloro-4-fluorophenylamine 
• 530145-55-2 2,3,4-trifluoro-1,5-phenylenebis(triethylsilane) 
• 530145-56-3 (5-bromo-2,3,4-trifluorophenyl)triethylsilane 
• 176317-02-5 1-bromo-2,3,4-trifluorobenzene 
• 1489-53-8 1,2,3-trifluorobenzene 

Downstream Products

• 137019-95-5 3,4,5-trifluoro-4'-(4-pentylcyclohexyl)-1,1'-biphenyl 
• 131819-22-2 1-(trans-4-pentylcyclohexyl)-3,4,5-trifluorobenzene 
• 148462-51-5 1-(Trans-4-heptylcyclohexyl)-3,4,5-trifluorobenzene 
• 131819-23-3 trans-4-(trans-4'-n-propylcyclohexyl)-cyclohexyl-3,4,5-trifluorobenzene 
• 137529-57-8 1-(trans-4-ethylcyclohexyl)-2-[trans-4-(3,4,5-trifluorophenyl)cyclohexyl]ethane 
• 137644-54-3 4'-Pentyl-4-(3,4,5-trifluoro-phenyl)-bicyclohexyl 
• 137529-56-7 1-(trans-4-pentylcyclohexyl)-2-[trans-4-(3,4,5-trifluorophenyl)cyclohexyl]ethane 
• 132123-39-8 4'-(trans-4-Propylcyclohexyl)-3,4,5-trifluorobiphenyl 

Relevant articles and documents

Green synthesis method of 3,4,5-trifluorobromobenzene

The invention discloses a green synthesis method of 3,4,5-trifluorobromobenzene. The green synthesis method comprises the following steps: adding 2,3,4-trifluoroaniline and water into a reactor, adding hydrobromic acid and hydrogen peroxide, and carrying out a hybrid reaction to obtain 2,3,4-trifluoro-6-bromoaniline after the reaction is ended; slowly adding a sulfuric acid solution of nitroso sulfuric acid into the prepared 2,3,4-trifluoro-6-bromoaniline, and carrying out a diazotization reaction to obtain a diazonium salt solution; and adding sodium hypophosphite and porous material-loaded copper oxide into the prepared diazonium salt solution as catalysts, conducting reacting, and sequentially carrying out distillation, alkali washing, water washing and reduced-pressure rectification on reaction liquid after the reaction is finished so as to obtain a target product. According to the method, nitrososulfuric acid replaces sodium nitrite to serve as a diazotization reagent, so no high-salt wastewater is discharged, production cost is reduced, and the method is more environmentally friendly; and hydrobromic acid serves as a bromine source, and hydrogen peroxide is added, so the utilization rate of bromine atoms is high, the adding amount of hydrobromic acid is reduced, and the amount of three wastes generated in implementation of the method is remarkably reduced.

Preparation method of 3, 4, 5-trifluorobromobenzene

The invention relates to a preparation method of 3, 4, 5-trifluorobromobenzene, belongs to the technical field of chemical synthesis, and solves the problem that a byproduct 3, 4, 5-trichloronitrobenzene generated in a process of preparing 3, 4-dichloronitrobenzene by introducing chlorine into parachloronitrobenzene cannot be effectively utilized. The method comprises the step of preparing 3, 4, 5-trifluorobromobenzene by taking 3, 4, 5-trichloronitrobenzene as a raw material. According to the technical scheme provided by the invention, the utilization rate of raw materials and the efficiencyof the process can be improved, and high-value utilization of byproducts is realized.

Preparation method of 3,4,5-trifluorobromobenzene

The invention belongs to the technical field of fine chemicals, and in particular relates to a preparation method of 3,4,5-trifluorobromobenzene. The method comprises the following steps: firstly, dissolving 1,2,3-trifluoro-benzene in an organic solvent; then adding a sodium bromide aqueous solution containing a buffer solution; dropwise adding sodium hypochlorite to react for bromination; desolventizing an organic phase to obtain a 3,4,5-trifluorobromobenzene coarse product; and carrying out melt crystallization on the coarse product to obtain 3,4,5-trifluorobromobenzene. The preparation method provided by the invention is simple, the product yield reaches over 94%, the product yield is high, and the content of the prepared 3,4,5-trifluorobromobenzene reaches over 99.5%, and the preparation process is mild, efficient, environment-friendly, safe and reliable.

PROCESS FOR THE PREPARATION OF ORGANIC BROMIDES

The present invention provides a process for the preparation of organic bromides, by a radical bromodecarboxylation of carboxylic acids with a bromoisocyanurate.

Organometallic control over the regiospecificity of functionalization reactions: 1,2,3-Trifluorobenzene and bromo derivatives thereof as substrates

In a case study, 1,2,3-trifluorobenzene was functionalized at each of the two vacant positions (producing the benzoic acids 1 and 2) and, in addition, bromine was introduced into all available positions (producing the benzoic acids 3-5). The required regioflexibility was achieved by applying novel organometallic recipes such as deprotonation-triggered halogen migrations and site-discriminating competitive halogen-metal permutations. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Method for producing tetrakis ( fluoroaryl) borate-magnesium compound

Fluoroaryl magnesium halide is reacted with a boron compound so that a molar ratio of the fluoroaryl magnesium halide to the boron compound is not less than 3.0 and not more than 3.7, so as to produce a tetrakis (fluoroaryl) borate·magnesium compound. With this method, there occurs no hydrogen fluoride which corrodes a producing apparatus and requires troublesome waste water treatment.

Fragmentation of radical anions of polyfluorinated benzoates

A comprehensive study of the symmetry forbidden fragmentation of short-lived radical anions (RAs) has been undertaken for the complete set of polyfluorinated benzoates (C6FnH5-nCO22, n = 1-5). The decay rate constants (kc) of RAs have been determined in aqueous alkaline solution (pH 13.4) by electron photoinjection (EPI) from mercury electrodes and were found to increase dramatically from ≤3 × 103 s-1 (3-F - C6H4CO2-) to (1.2 ± 0.8) × 109 s-1 (C6F5CO2-). The regioselectivity of C-F bond cleavage in the RA fragmentation has been revealed by structure assignment of reduction products of the polyfluorinated benzoic acids by Na, K, and Zn in liquid NH3, as well as by Zn in aqueous NH3 and aqueous alkaline solutions. The kc values depend on the position of the cleaved fluorine to the CO2- group generally in the order para > ortho > meta, and to sharply increase if adjacent fluorine atoms are present. The observed trends reveal that the kinetics of the RA fragmentation reaction is not controlled by the reaction thermodynamics. Semiempirical UHF/INDO calculations, the validity of which has been confirmed by ab initio ROHF/6-31+G calculations, were done to rationalize the observed trends. The reaction transition state (TS) was considered to arise from the RA's and 2*states crossing avoided due to out-of-plane deviation of the cleaving C-F bond. The satisfactory linear correlation (R = 0.96) between the model reaction energy barrier Ea and log kc has been achieved with modeling the local solvation of the CO2- group by its protonation.