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

Chemical Properties

colourless liquid

General Description

Crystal structure 1,2,3-trifluorobenzene was reported. The microwave spectrum of 1,2,3-trifluorobenzene was studied using a molecular beam Fourier transform microwave spectrometer. Laser-induced fluorescence spectra of the radical cation of 1,2,3-trifluorobenzene was determined in both the gas phase and solid Ne matrices.

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

Upstream product

• 36556-42-0 4-chloro-1,2,3-trifluorobenzene 
• 226396-32-3 (2,3,4-trifluorophenyl)boronic acid 
• 392-56-3 Hexafluorobenzene 
• 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 
• 602-94-8 Pentafluorobenzoic 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 
• 1489-52-7 1H,2H,3H-Heptafluor-cyclohexen 

Downstream Products

• 85068-28-6 2,6-difluorophenylacetic acid 
• 145689-41-4 2-(2,3-difluorophenyl)acetic acid 
• 202000-98-4 ethyl cyano(2,6-difluorophenyl)acetate 
• 61079-72-9 2,3,4,-trifluorobenzoic acid 
• 1055876-64-6 2,3-difluoro-1-(p-tolylthio)benzene 
• 1055876-65-7 1,3-difluoro-2-(p-tolylthio)benzene 
• 1055876-67-9 2-fluoro-1,3-bis(p-tolylthio)benzene 
• 1055876-66-8 3-fluoro-1,2-bis(p-tolylthio)benzene 
• 1055876-68-0 1,2,3-tris(p-tolylthio)benzene 
• 462-06-6 fluorobenzene 
• 367-11-3 ortho-difluorobenzene 
• 65-85-0 benzoic acid 
• 4519-39-5 2,3-difluorobenzoic acid 
• 455-86-7 3,4-Difluorobenzoic 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.