Chloropentafluorobenzene

Base Information

• Chemical Name: Chloropentafluorobenzene
• CAS No.: 344-07-0
• Molecular Formula: C6ClF5
• Molecular Weight: 202.511
• Hs Code.: 29039990
• European Community (EC) Number: 206-450-6
• NSC Number: 96886
• UNII: 3D8A2YE2U8
• DSSTox Substance ID: DTXSID4059837
• Nikkaji Number: J95.789E
• Wikidata: Q26840781
• Mol file: 344-07-0.mol

Synonyms:chloropentafluorobenzene

Chemical Property of Chloropentafluorobenzene

Chemical Property:

• Appearance/Colour: Clear colourless liquid
• Melting Point: -15.66°C
• Refractive Index: n20/D 1.424(lit.)
• Boiling Point: 123.8 °C at 760 mmHg
• Flash Point: 29.5 °C
• PSA: 0.00000
• Density: 1.654 g/cm³
• LogP: 3.03550
• Storage Temp.: Refrigerator
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 201.9608685
• Heavy Atom Count: 12
• Complexity: 150

Purity/Quality:

97% ^*data from raw suppliers

Chloropentafluorobenzene >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 20-36/37/38
• Safety Statements: 23-24/25-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1(=C(C(=C(C(=C1F)F)Cl)F)F)F
• General Description: Chloropentafluorobenzene (also known as Pentafluorochlorobenzene or Pentafluorophenylchloride) participates in nucleophilic aromatic substitution reactions via halogen-metal exchange rather than a traditional S_N2Ar mechanism, leading to the formation of pentafluorophenyl carbanions and yielding products such as [C6F5Fe(CO)2Cp], chloroperfluoropolyphenyls, and [CpFe(CO)2]-. The reaction pathway and product distribution are influenced by reactant ratios, solvent choice, counterion type (e.g., K+, K+-18-crown-6, or PPN+), and temperature.

Technology Process of Chloropentafluorobenzene

There total 56 articles about Chloropentafluorobenzene 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: 93.0%

pentafluorophenylthiol (771-62-0) → 1-chloro-2,3,4,5,6-pentafluorobenzene (344-07-0)

Guidance literature:

pentafluorophenylthiol; With phosphorus pentachloride; at 201 - 203 ℃; for 5h; Sealed tube;

With sodium carbonate; In water; for 4h; Time; Temperature;

DOI:10.1134/S1070428016020068

Reference yield: 93.0%

pentafluorobenzenesulfenyl chloride (27918-31-6) → 1-chloro-2,3,4,5,6-pentafluorobenzene (344-07-0)

Guidance literature:

With chlorine; at 395 - 405 ℃; for 0.295h;

DOI:10.1007/s11178-006-0012-1

Reference yield: 90.0%

bis(pentafluorophenyl) disulfide (1494-06-0) → 1-chloro-2,3,4,5,6-pentafluorobenzene (344-07-0)

Guidance literature:

With chlorine; at 405 - 410 ℃; for 0.295h;

DOI:10.1007/s11178-006-0012-1

upstream raw materials:

hexachlorobenzene

Hexafluoropropene oxide

cis-5,6-dichlorohexafluorocyclohexa-1,3-diene

Hexafluorobenzene

Downstream raw materials:

1-fluoroethylene

tetrafluorobezyne

4-chlorononafluorodiphenylamine

methyl 9-pentafluorophenylfluorene-9-carboxylate

Refernces

The reaction of the [CpFe(CO)₂]^- Anion with pentafluorochlorobenzene: Nucleophilic aromatic substitution by halogen - Metal exchange

10.1002/(SICI)1521-3765(19980710)4:7<1169::AID-CHEM1169>3.0.CO;2-H

The research study on the reaction between the [CpFe(CO)2]- anion and pentafluorochlorobenzene, aiming to understand the mechanism of nucleophilic aromatic substitution via a halogen-metal exchange process. The study concludes that the reaction does not follow a traditional S_N2Ar mechanism, but instead involves the formation of pentafluorophenyl carbanions, with the key step being the halogen-metal exchange. The reaction yields various products, including [C6F5Fe(CO)2Cp], chloroperfluoropolyphenyls, and [CpFe(CO)2]-, with the distribution influenced by factors such as the reactant ratio, solvent, counterion, and temperature. The research also involved the use of radical and carbanionic traps to control the reaction pathway and the counterions K+, K+-18-crown-6, and [(C2H5)2P-N=P(C2H5)2]+ (PPN+).