1489-53-8

Basic information

• Product Name: 1,2,3-Trifluorobenzene
• Synonyms: 1,2,3-TRIFLUOROBENZENE;1,2,3-Trifluorobenzene, 98+%;3-chloro-4-flurobenzonitrile;1,2,3-Trifluorobenzene 99%;1,2,3-Trifluorobenzene99%;1,2,3-Trifluorobenze;1,2,3-fluorobenzene;1,2,3-Trifluorobenzene, 99% 1GR
• CAS NO: 1489-53-8
• Molecular Formula: C₆H₃F₃
• Molecular Weight: 132.08
• Product Categories: Aryl Fluorinated Building Blocks;Building Blocks;Chemical Synthesis;Fluorinated Building Blocks;Halogenated Hydrocarbons;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks;Industrial/Fine Chemicals;Fluorobenzene;Miscellaneous;Aryl;C6;Halogenated Hydrocarbons
• Mol File: 1489-53-8.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 94-95 °C(lit.)
• Flash Point: 25 °F
• Appearance: colourless liquid
• Density: 1.28 g/mL at 25 °C(lit.)
• Vapor Pressure: 56.1mmHg at 25°C
• Refractive Index: n20/D 1.423(lit.)
• Storage Temp.: Flammables area
• Stability: Stable. Highly flammable. Incompatible with strong oxidizing agents.
• BRN: 1862388
• CAS DataBase Reference: 1,2,3-Trifluorobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3-Trifluorobenzene(1489-53-8)
• EPA Substance Registry System: 1,2,3-Trifluorobenzene(1489-53-8)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36/37/39-37/39-33-7/9
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 1489-53-8(Hazardous Substances Data)

Usage

Description

1,2,3-Trifluorobenzene is an aromatic compound with the chemical formula C6H3F3. It is a colorless liquid and features a benzene ring with three fluorine atoms substituted at the 1, 2, and 3 positions. The compound has been studied through various spectroscopic techniques, including microwave spectroscopy and laser-induced fluorescence, providing insights into its crystal structure and molecular properties.

Uses

Used in Pharmaceutical Industry:
1,2,3-Trifluorobenzene is used as a building block for the synthesis of various pharmaceutical compounds. Its unique structure and properties make it a valuable intermediate in the development of new drugs, particularly those targeting specific receptors or enzymes in the body.
Used in Chemical Synthesis:
1,2,3-Trifluorobenzene serves as a versatile intermediate in the synthesis of a wide range of organic compounds, including agrochemicals, dyes, and specialty chemicals. Its reactivity and stability contribute to its utility in various chemical reactions, enabling the production of diverse products.
Used in Materials Science:
The compound's properties, such as its stability and reactivity, make it suitable for use in the development of new materials with specific characteristics. For example, 1,2,3-trifluorobenzene can be incorporated into the design of advanced polymers, coatings, and other materials with tailored properties for various applications.
Used in Research and Development:
1,2,3-Trifluorobenzene is utilized as a model compound in academic and industrial research to study the effects of fluorine substitution on the properties of aromatic systems. Its unique structure allows researchers to investigate various aspects of molecular interactions, electronic properties, and reaction mechanisms, contributing to the advancement of scientific knowledge in the field of chemistry.

InChI:InChI=1/C6H3F3/c7-4-2-1-3-5(8)6(4)9/h1-3H

Upstream product

• 31399-11-8 2,3,5-trifluorobicyclo<2.2.0>hexa-2,5-diene 
• 392-56-3 Hexafluorobenzene 
• 602-94-8 Pentafluorobenzoic acid 
• 226396-32-3 (2,3,4-trifluorophenyl)boronic acid 
• 2367-82-0 1,2,3,5-tetrafluorobenzene 
• 551-62-2 1,2,3,4-tetrafluorobenzene 
• 363-72-4 Pentafluorobenzene 
• 143418-49-9 3,4,5-trifluorophenylboronic acid 
• 462-06-6 fluorobenzene 
• 7732-18-5 water 
• 827-13-4 1,2,4-trichlorotrifluorobenzene 
• 827-12-3 1,2,3-trichloro-4,5,6-trifluorobenzene 
• 319-88-0 1,3,5-trichlorotrifluorobenzene 
• 36556-42-0 4-chloro-1,2,3-trifluorobenzene 

Downstream Products

• 437-82-1 1,3-difluoro-2-methoxybenzene 
• 134364-69-5 2.3-difluoroanisole 
• 75-15-0 carbon disulfide 
• 6418-38-8 2,3-difluorophenol 
• 363-52-0 3-fluorocatechol 
• 363598-55-4 trimethyl(2,3,4-trifluorophenyl)silane 
• 530145-55-2 2,3,4-trifluoro-1,5-phenylenebis(triethylsilane) 
• 459425-36-6 2,3,4-trifluoro-1,5-diiodobenzene 
• 203916-59-0 2,3,4-trifluoro-5-iodobenzoic acid 
• 35997-04-7 (2,3,4-trifluoro-1,5-phenylene)bis(trimethylsilane) 
• 455-38-9 3-fluorobenzoic acid 
• 455-86-7 3,4-Difluorobenzoic acid 
• 4519-39-5 2,3-difluorobenzoic acid 
• 65-85-0 benzoic acid 

Relevant articles and documents

Stoichiometric and catalytic C-F bond activation by the trans-dihydride NHC complex [Ru(IEt2Me2)2-(PPh3)2H2] (IEt2Me2 = 1,3-diethyl-4,5-dimethylimidazol-2-ylidene)

The room temperature reaction of C6F6 or C6F5H with [Ru(IEt2Me2)2(PPh3)2H2] (1; IEt2Me2 = 1,3-diethyl-4,5-dimethylimidazol-2-ylidene) generated a mixture of the trans-hydride fluoride complex [Ru(IEt2Me2)2(PPh3)2HF] (2) and the bis-carbene pentafluorophenyl species [Ru(IEt2Me2)2(PPh3)(C6F5)H] (3). The formation of 3 resulted from C-H activation of C6F5H (formed from C6F6via stoichiometric hydrodefluorination), a process which could be reversed by working under 4 atm H2. Upon heating 1 with C6F5H, the bis-phosphine derivative [Ru(IEt2Me2)(PPh3)2(C6F5)H] (4) was isolated. A more efficient route to 2 involved treatment of 1 with 0.33 eq. of TREAT-HF (Et3N·3HF); excess reagent gave instead the [H2F3]- salt (5) of the known cation [Ru(IEt2Me2)2(PPh3)2H]+. Under catalytic conditions, 1 proved to be an active precursor for hydrodefluorination, converting C6F6 to a mixture of tri, di and monofluorobenzenes (TON = 37) at 363 K with 10 mol% 1 and Et3SiH as the reductant.

Rhodium catalyzed, carbon-hydrogen bond directed hydrodefluorination of fluoroarenes

[CpRhCl(μ-Cl)]2 is reported as a highly efficient and selective precatalyst for the hydrodefluorination of perfluoroarenes using a hydrocarbon-soluble aluminum dihydride as the terminal reductant. Reactions are directed to cleave a C-F bond adjacent to an existing C-H bond with high regioselectivity (98.5-99%). A heterobimetallic complex containing an extremely rare Al-H-Rh functional group has been isolated and shown to be catalytically competent.

Catalytic Hydrodefluorination of Fluoroarenes Using Ru(IMe4)2L2H2 (IMe4 = 1,3,4,5-Tetramethylimidazol-2-ylidene; L2 = (PPh3)2, dppe, dppp, dppm) Complexes

The all-trans isomer of Ru(IMe4)2(PPh3)2H2 (ttt-4; IMe4 = 1,3,4,5-tetramethylimidazol-2-ylidene) reacts with C6F6 at 70 °C to afford the hydride fluoride complex Ru(IMe4)2(PPh3)2HF (ttt-6). At room temperature, ttt-6 reacts with Et3SiH to give a mixture of products, one of which is assigned as the silyl trihydride complex Ru(IMe4)2(PPh3)(SiEt3)H3 (8) by comparison to the isolated and structurally characterized analogue Ru(IMe4)2(PPh3)(SiPh3)H3 (9). As ttt-4 was re-formed cleanly upon heating ttt-6 with Et3SiH, it was tested in the catalytic hydrodefluorination (HDF) of C6F6 (10 mol %, 90 °C), along with 9, Ru(IMe4)2(P-P)HF (P-P = Ph2P(CH2)2PPh2 (dppe, cct-13), Ph2P(CH2)3PPh2 (dppp, cct-14), Ph2PCH2PPh2 (dppm, cct-15)), Ru(IEt2Me2)2(PPh3)2HF (cct-7; IEt2Me2 = 1,3-diethyl-4,5-dimethylimidazol-2-ylidene)), and Ru(IEt2Me2)2(dppe)2HF (cct-16) for comparison. Both cct-13 and cct-14 brought about near-quantitative conversion to C6FH5 in 24 h, in comparison to ca. 50% conversion with ttt-4 in 144 h.