2367-82-0

Basic information

• Product Name: 1,2,3,5-Tetrafluorobenzene
• Synonyms: 1,2,3,5-TETRAFLUOROBENZENE;1,2,4,6-Tetrafluorobenzene;1,3,4,5-Tetrafluorobenzene;benzene,1,2,3,5-tetrafluoro-;1,2,3,5-tetrafluoronitrobenzene;1 2 3 5-TETRAFLUOROBENZENE TECH. 85%;4-flurobenzalcohol;1,2,3,5-Tetrafluorobenzene 97%
• CAS NO: 2367-82-0
• Molecular Formula: C₆H₂F₄
• Molecular Weight: 150.07
• EINECS: 219-126-4
• Product Categories: Fluorobenzene;Aryl;C6;Halogenated Hydrocarbons
• Mol File: 2367-82-0.mol
• Article Data: 15

Chemical Properties

• Melting Point: -48 °C
• Boiling Point: 83 °C(lit.)
• Flash Point: 40 °F
• Appearance: clear colorless liquid
• Density: 1.393 g/mL at 25 °C(lit.)
• Vapor Pressure: 82.4mmHg at 25°C
• Refractive Index: n20/D 1.404(lit.)
• Storage Temp.: Refrigerator
• Water Solubility: 743.1mg/L(25 oC)
• CAS DataBase Reference: 1,2,3,5-Tetrafluorobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,5-Tetrafluorobenzene(2367-82-0)
• EPA Substance Registry System: 1,2,3,5-Tetrafluorobenzene(2367-82-0)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-7-33-29-7/9
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 2367-82-0(Hazardous Substances Data)

Usage

Description

1,2,3,5-Tetrafluorobenzene is an organic compound with the molecular formula C6H2F4. It is a clear colorless liquid and features a benzene ring with four fluorine atoms substituting the hydrogen atoms at the 1, 2, 3, and 5 positions. The crystal structure and nuclear magnetic resonance spectrum (1H and 19F) of this compound have been studied, indicating its significance in chemical research and potential applications.

Uses

Used in Chemical Synthesis:
1,2,3,5-Tetrafluorobenzene is used as a building block for the synthesis of various fluorinated organic compounds. Its unique structure and properties make it a valuable intermediate in the production of pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Material Science:
1,2,3,5-Tetrafluorobenzene is used as a component in the development of advanced materials, such as polymers and coatings, due to its fluorine content, which can impart desirable properties like chemical resistance, non-stick surfaces, and low refractive index.
Used in Electronics Industry:
1,2,3,5-Tetrafluorobenzene is used as a precursor for the production of specialty materials in the electronics industry, such as insulating films and etching agents, taking advantage of its stability and fluorine content.
Used in Fluorine Chemistry Research:
1,2,3,5-Tetrafluorobenzene serves as a model compound for studying the effects of fluorine substitution on the chemical and physical properties of aromatic systems, contributing to the understanding of fluorine chemistry and its applications in various fields.

InChI:InChI=1/C6H2F4/c7-3-1-4(8)6(10)5(9)2-3/h1-2H

Upstream product

• 363-72-4 Pentafluorobenzene 
• 357-85-7 1,5-Di-H-hexafluoro-1,4-cyclohexadiene 
• 363-80-4 2,3,5-trifluoro aniline 
• 75411-00-6 1,2,3,5-tetrafluorobicyclo<2.2.0>hexa-2,5-diene 
• 23657-35-4 1,2,3,4,5,6-hexafluoro-7,8-diazatricyclo<4.3.0.0^2,5>nona-3,7-diene 
• 1678-91-7 ethyl-cyclohexane 
• 75-77-4 chloro-trimethyl-silane 
• 1559-86-0 2-bromo-1,3,4,5-tetrafluorobenzene 
• 13332-15-5 1,2,3,5-tetrafluoro-4-iodobenzene 
• 1559-87-1 1,3-dibromo-2,4,5,6-tetrafluorobenzene 
• 67815-57-0 1,3-Diiodo-2,4,5,6-tetrafluorobenzene 
• 878-43-3 1H-heptafluorocyclohexa-1,3-diene 
• 7732-18-5 water 
• 511295-00-4 2,3,4,6-tetrafluorophenyl(dihydroxy)borane 

Downstream Products

• 314-41-0 1,2,3,5-tetrafluoro-4-nitrobenzene 
• 53104-18-0 N-tert-Butyl-N-(2,3,4,6-tetrafluoro-phenyl)-hydroxylamine 
• 1559-86-0 2-bromo-1,3,4,5-tetrafluorobenzene 
• 13332-15-5 1,2,3,5-tetrafluoro-4-iodobenzene 
• 20002-14-6 2,4,5,6-Tetrafluoro-1,3-dinitrobenzene 
• 4920-36-9 2,3,6-trifluoro-4-methoxybenzene 
• 76980-85-3 1,2,3,4,5,6,7-Heptafluoro-8-(2,3,4,6-tetrafluoro-phenyl)-naphthalene 
• 76980-84-2 1,5-bis(3-H-tetrafluorophenyl)hexafluoronaphthalene 
• 76980-87-5 1,2,3,4,5,7-Hexafluoro-6-methyl-8-(2,3,4,6-tetrafluoro-phenyl)-naphthalene 
• 76980-86-4 1,2,3,4,6,8-Hexafluoro-5-(2,3,4,6-tetrafluoro-phenyl)-naphthalene 
• 96631-23-1 1,3-Diethoxy-2,5-difluoro-benzene 
• 70416-05-6 1,2,3,5-Tetrakis(ethylthio)benzene 
• 67815-57-0 1,3-Diiodo-2,4,5,6-tetrafluorobenzene 
• 72323-96-7 1,2,3,5-tetrafluorobenzene disulfonic acid 

Relevant articles and documents

Stopped-Flow 19F NMR Spectroscopic Analysis of a Protodeboronation Proceeding at the Sub-Second Time-Scale

In-situ NMR spectroscopic analysis of homogeneous reactions is an essential tool for mechanistic analysis in organic and organometallic chemistry. However, rapid non-equilibrium reactions, that are initiated by mixing, require specialized approaches. We report herein on a study of the factors that ensure quantitative results in a recently-developed technique for stopped-flow NMR spectroscopy. The influence of some of the key parameters on quantitation is studied by 19F NMR spectroscopic analysis of the kinetics and activation parameters for the base-catalyzed protodeboronation of highly-reactive polyfluorinated arylboronic acids, with half-lives as low as 0.1 seconds. The effects of spin relaxation, pre-magnetization, heat-transfer versus reaction enthalpy, and mixing-efficiency are analyzed in detail. We also compare and contrast choice of pulse angle, interscan delay, and use of pseudo real-time by interleaving, as means to achieve an optimal balance between temporal resolution and sensitivity.

Base-Catalyzed Aryl-B(OH)2 Protodeboronation Revisited: From Concerted Proton Transfer to Liberation of a Transient Aryl Anion

Pioneering studies by Kuivila, published more than 50 years ago, suggested ipso protonation of the boronate as the mechanism for base-catalyzed protodeboronation of arylboronic acids. However, the study was limited to UV spectrophotometric analysis under acidic conditions, and the aqueous association constants (Ka) were estimated. By means of NMR, stopped-flow IR, and quenched-flow techniques, the kinetics of base-catalyzed protodeboronation of 30 different arylboronic acids has now been determined at pH > 13 in aqueous dioxane at 70 °C. Included in the study are all 20 isomers of C6HnF(5-n)B(OH)2 with half-lives spanning 9 orders of magnitude: a and Sδ values, kinetic isotope effects (2H, 10B, 13C), linear free-energy relationships, and density functional theory calculations, we have identified a mechanistic regime involving unimolecular heterolysis of the boronate competing with concerted ipso protonation/C-B cleavage. The relative Lewis acidities of arylboronic acids do not correlate with their protodeboronation rates, especially when ortho substituents are present. Notably, 3,5-dinitrophenylboronic acid is orders of magnitude more stable than tetra-and pentafluorophenylboronic acids but has a similar pKa.

Microwave-accelerated fluorodenitrations and nitrodehalogenations: expeditious routes to labeled PET ligands and fluoropharmaceuticals

Methods for the expeditious fluorination of arenes have been investigated, using readily available fluoride sources. An optimized procedure for microwave-accelerated fluorodenitration has been developed, giving good to excellent yields in less than 10 min, rendering it practical for use in the preparation of F18 labeled ligands for PET imaging. Application of the method in the synthesis of CNS agents is demonstrated, and a practical method for the preparation of substrates is also presented.