1,2,4,5-Tetrafluorobenzene

Base Information

• Chemical Name: 1,2,4,5-Tetrafluorobenzene
• CAS No.: 327-54-8
• Molecular Formula: C6H2F4
• Molecular Weight: 150.075
• Hs Code.: 29039990
• European Community (EC) Number: 206-319-3
• NSC Number: 10249
• UNII: AB3CL8US2H
• DSSTox Substance ID: DTXSID90186367
• Nikkaji Number: J28K
• Wikidata: Q72505063
• Mol file: 327-54-8.mol

Synonyms:1,2,4,5-tetrafluorobenzene

Chemical Property of 1,2,4,5-Tetrafluorobenzene

Chemical Property:

• Appearance/Colour: Clear colourless liquid
• Vapor Pressure: 64.2mmHg at 25°C
• Melting Point: 4 °C(lit.)
• Refractive Index: n20/D 1.407(lit.)
• Boiling Point: 90.2 °C at 760 mmHg
• Flash Point: 16.1 °C
• PSA: 0.00000
• Density: 1.412 g/cm³
• LogP: 2.24300
• Storage Temp.: Flammables area
• Water Solubility.: Not miscible or difficult to mix in water.
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 150.00926271
• Heavy Atom Count: 10
• Complexity: 90.3

Purity/Quality:

99% ^*data from raw suppliers

1,2,4,5-Tetrafluorobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36/37/39-37/39-33-7/9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C(=CC(=C1F)F)F)F
• Uses: It is employed as intermediate in organic synthesis. It is also used as pharmaceutical intermediate.

Technology Process of 1,2,4,5-Tetrafluorobenzene

There total 75 articles about 1,2,4,5-Tetrafluorobenzene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

Hexafluorobenzene (392-56-3) → 1,2,4,5-Tetrafluorobenzene (327-54-8) + Pentafluorobenzene (363-72-4)

Guidance literature:

With [Ru(IMe₄)₄H₂]; HSiPh₃; In benzene; at 120 ℃; for 740h; regioselective reaction; Catalytic behavior;

DOI:10.1002/anie.201610820

Reference yield: 74.0%

Hexafluorobenzene (392-56-3) → 1,2,4,5-Tetrafluorobenzene (327-54-8) + 1,2,3,4-tetrafluorobenzene (551-62-2) + Pentafluorobenzene (363-72-4) + 1,2,4-trifluorobenzene (367-23-7)

Guidance literature:

With (1,3-dimethylimidazolin-2-ylidene)*AlH₃; In 5,5-dimethyl-1,3-cyclohexadiene; at 135 ℃; for 25h;

DOI:10.1002/ejic.201800589

Reference yield: 60.0%

bromopentafluorobenzene (344-04-7) → 1,2,4,5-Tetrafluorobenzene (327-54-8) + Pentafluorobenzene (363-72-4)

Guidance literature:

With water; triethylphosphine; In 1,4-dioxane; at 120 ℃; for 1h; Reagent/catalyst; Schlenk technique; Inert atmosphere; Glovebox;

DOI:10.1039/c9nj00721k

upstream raw materials:

2,4,5-trifluoroaniline

1,2,4,5-tetrachlorobenzene

Pentafluorobenzene

1,2,4,5-tetrafluorobicyclo<2.2.0>hexa-2,5-diene

Downstream raw materials:

1,4-dibromotetrafluorobenzene

1,4-diiodo-2,3,5,6-tetrafluorobenzene

2,5-Difluoro-1,4-benzoquinone

1,2,3,4,5,6-hexachloro-1,2,4,5-tetrafluoro-cyclohexane

Refernces

• 1、 Cybulski, Mateusz K.,McKay, David,Macgregor, Stuart A.,Mahon, Mary F.,Whittlesey, Michael K.. "Room Temperature Regioselective Catalytic Hydrodefluorination of Fluoroarenes with trans-[Ru(NHC)4H2] through a Concerted Nucleophilic Ru?H Attack Pathway". . p. 1515 - 1519. Retrieved 2017.
• 2、 Zámostná, Lada,Ahrens, Mike,Braun, Thomas. "Catalytic hydrodefluorination of fluoroaromatics with silanes as hydrogen source at a binuclear rhodium complex: Characterization of key intermediates". . p. 132 - 142. Retrieved 2013.
• 3、 Segarra, Candela,Mas-Marza, Elena,Lowe, John P.,Mahon, Mary F.,Poulten, Rebecca C.,Whittlesey, Michael K.. "Ring-expanded N-heterocyclic carbene complexes of rhodium with bifluoride, fluoride, and fluoroaryl ligands". . p. 8584 - 8590. Retrieved 2012.
• 4、 Li, Junye,Zheng, Tingting,Sun, Hongjian,Li, Xiaoyan. "Selectively catalytic hydrodefluorination of perfluoroarenes by Co(PMe 3)4 with sodium formate as reducing agent and mechanism study". . p. 13048 - 13053. Retrieved 2013.
• 5、 Adonin, N Yu,Prikhod'ko, S. A.,Shabalin, A Yu.. "New catalytic systems with chemically fixed nickel complexes in the reactions of reductive activation of C-F bonds in ionic liquid media". . . Retrieved 2021/08/03.
• 6、 Schoch, Timothy D.,Mondal, Mukulesh,Weaver, Jimmie D.. "Catalyst-Free Hydrodefluorination of Perfluoroarenes with NaBH4". supporting information. p. 1588 - 1593. Retrieved 2021/03/03.