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Hexafluorobenzene

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Hexafluorobenzene is a colorless, volatile liquid organic compound with the molecular formula C6F6. It is a highly fluorinated aromatic compound used as a specialty chemical in various laboratory applications.

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Lab products found in correlation

Tetrahydrofuran, by Merck Group (3 mentions) Toluene, by Thermo Fisher Scientific (2 mentions) Propargylamine, by Merck Group (2 mentions) Sodium ascorbate, by Merck Group (2 mentions) Neocuproine, by Merck Group (2 mentions) Hexa ethylene glycol dithiol, by Merck Group (2 mentions) Peg 600 diol, by Merck Group (2 mentions) Deuterobenzene, by Cambridge Isotopes (2 mentions) Thiourea, by Chem-Impex (2 mentions) Hexafluoroisopropanol hfip, by Thermo Fisher Scientific (2 mentions) Triethylamine, by Merck Group (2 mentions) Copper 2 acetate, by Thermo Fisher Scientific (2 mentions) Oxalyl chloride, by Merck Group (2 mentions) Deuterochloroform, by Cambridge Isotopes (2 mentions) Deuterated dimethyl sulfoxide, by Cambridge Isotopes (2 mentions) Glycerol ethoxylate, by Merck Group (2 mentions) Acetone, by Thermo Fisher Scientific (2 mentions) Acetonitrile, by Honeywell (1 mentions) 4 methoxyphenol, by Thermo Fisher Scientific (1 mentions) Na2co3, by Carl Roth (1 mentions)

8 protocols using hexafluorobenzene

1

Synthesis of Fluorinated Aromatic Ethers from PFPE Diol

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Example 2

A PFPE diol precursor [PFPE-2] having the following structure: HOCH2CF2O—(CF2O)n(CF2CF2O)m(CF2CF2CF2O)p(CF2CF2CF2CF2O)q—CF2CH2OH wherein n=6.27, m=8.03, and (p+q)=0.09; the number average molecular weight (Mn) of the (per)fluoropolyether chain is equal to 1540 Dalton, was used.

100 g of the PFPE-2 were mixed with 50 g of hexafluorobenzene (from Sigma-Aldrich) and 11 g of KOH powder (title 85%) was added to the liquid mixture at room temperature.

The reaction mass was kept, under stirring, at 60° C. for 6 hours.

The resulting solution was washed two times with aqueous HCl (0.1N) and dried at reduced pressure resulting 118.4 g of colourless liquid product. The 19F NMR analysis showed a total conversion (>99% by mol) of the CF2CH2OH groups to the correspondent aromatic derivative —CF2CH2OC6F5.

US10906999B2. Fluoroelastomer compositions (2021-02-02). SOLVAY SPECIALTY POLYMERS ITALY S.P.A. [IT]. Inventors: Marco Avataneo [IT], Liubov Chernysheva [IT], Ugo De Patto [IT].
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2

Synthesis and Characterization of Organic Compounds

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4,7-Dibromobenzo[1,2,5]thiadiazole (>98%),
(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol (>98%),
dimethylformamide (>99.5%), 1,4-dioxane (stab. with BHT, >99%),
glycidyl
methacrylate (stab. with MEHQ, >99.5%), tetrahydrothiophene (>99%),
2-(ethylthio)ethanol (>98%), 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane
(>98%), and 3,4-dimethoxybenzylamine (>97%) were purchased from
Tokyo
Chemical Industry (TCI). Methacryloyl chloride (stab. with MEHQ,>97%),
dimethyl sulfoxide (>99.5%,anhydrous), 2-bromobenzaldehyde (98%),
4-((((2-carboxyethyl)thio)carbonothioyl)thio)-4-cyanopentanoic acid
(95%), hexafluorobenzene (99%), hexafluoro-2-propanol (>99%), and
4-tert-butylbenzylamine (97%) were purchased from
Sigma Aldrich. Tetrakis(triphenylphosphane)palladium (99%) and benzyl
amine (99%) were purchased from ACROS Organics. Methyl-p-tolylsulfide (97%), benzyl methacrylate (stab. with 4-Methoxy phenol,
98%), and 4,4′-azobis(4-cyanopentanoic acid) (98%) were purchased
from Alfa Aesar. Acetonitrile (>99.9%) was purchased from Honeywell.
Toluene (>99.8%), ethanol (absolute), and dichloromethane (>99%)
were
purchased from Fisher Scientific. Na2CO3 (>99.5%)
was purchased from Carl Roth. Deuterated dichloromethane (99.6%) was
purchased from Deutero GmbH. Regenerated cellulose dialysis tubing
(Sevapor 3, MWCO 3500, 16 mm diameter) was purchased from Serva.
Heuer J., Kuckhoff T., Li R., Landfester K, & Ferguson C.T. (2023). Tunable Photocatalytic Selectivity by Altering the Active Center Microenvironment of an Organic Polymer Photocatalyst. ACS Applied Materials & Interfaces, 15(2), 2891-2900.
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3

Preparation and Handling of Air- and Moisture-Sensitive Reagents

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Anhydrous acetonitrile (MeCN),
dichloromethane (CH2Cl2), benzene, tetrahydrofuran
(THF), pentane, and toluene solvents for air- and moisture-sensitive
manipulations were purchased from Sigma-Aldrich and further dried
by passage through columns of activated alumina, degassed by at least
three freeze–pump–thaw cycles, and stored under N2 prior to use. Hexamethyldisiloxane (HMDSO) was degassed by
at least three freeze–pump–thaw cycles and stored over
activated 4 Å molecular sieves under N2 prior to use.
Methanol (Drisolv) was purchased from EMD Millapore and was used as
received. Deuterated solvents were purchased from Cambridge Isotope
Laboratories. Acetonitrile-d3, DCM-d2, and THF-d8 were
placed an in oven-dried sealable flask and degassed by freeze–pump–thaw
cycles and then stored over activated 4 Å molecular sieves under
N2 prior to use. AgCF3 was prepared according
to a published procedure.59 (link) Silver fluoride
(Strem), TMSCF3 (Oakwood), Umemoto’s reagent (Sigma),
and hexafluorobenzene (Sigma) were all used as received. [(OCO)Co(THF)],36 (link) [(OCO)Co(THF)2]OTf (IV),36 (link) and [(OCO)Co(CF3)(MeCN)]
(I)35 (link) were prepared by published
procedures.
Kuehner C.S., Hill A.G., Harris C.F., Owens C.A., Bacsa J, & Soper J.D. (2023). Catalytic C–H Trifluoromethylation of Arenes and Heteroarenes via Visible Light Photoexcitation of a Co(III)–CF3 Complex. ACS Catalysis, 13(20), 13607-13617.
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4

Fluorinated Clickable Polymer Synthesis

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All chemicals were used as provided without further purification unless noted otherwise. Tetrahydrofuran, triethylamine, oxalyl chloride, propargyl amine, sodium ascorbate, neocuproine, hexa (ethylene glycol) dithiol, glycerol ethoxylate, PEG 600 diol and hexafluorobenzene were purchased from Sigma Aldrich. Deuterobenzene, deuterated dimethyl sulfoxide and deuterochloroform were purchased from Cambridge Isotope Laboratories (CIL). Copper(ii) acetate was obtained from Acros Organics and 2,2-dimethoxy-2-phenylacetophenone (DMPA) from TCI. TBTA was synthesized following a previously published procedure.43 Perfluorotripropylamine (FC 3283), methoxyperfluorobutane (HFE 7100), 2-(trifluoromethyl)-3-ethoxydodecafluorohexane (HFE 7500) and Krytox FSH were obtained from Miller-Stephenson. Acetonitrile (MeCN) was obtained from EMD and hexafluoroisopropanol (HFIP) from Alfa-Aesar. Thiourea was purchased from Chem-Impex International and ethanol, methanol, sodium hydroxide and hydrochloric acid were obtained from Macron Fine Chemicals.
Scanga R., Chrastecka L., Mohammad R., Meadows A., Quan P.L, & Brouzes E. (2018). Click chemistry approaches to expand the repertoire of PEG-based fluorinated surfactants for droplet microfluidics. RSC Advances, 8(23), 12960-12974.
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5

Preparation of Perfluoropolyether Benzyl Ether

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Example 1

A PFPE diol precursor [PFPE-1] having the following structure: HOCH2CF2O—(CF2O)e(CF2CF2O)m(CF2CF2CF2O)e(CF2CF2CF2CF2O)q—CF2CH2OH

wherein n=4.90, m=4.75, and (p+q)=0; the number average molecular weight (Mn) of the (per)fluoropolyether chain is equal to 1060 Dalton was used.

100 g of the PFPE-1 were mixed with 70 g of hexafluorobenzene (from Sigma-Aldrich) and 16 g of KOH powder (title 85%) were added to the liquid mixture at room temperature. The reaction mass was kept, under stirring, at 60° C. for 6 hours. The resulting solution was washed two times with aqueous HCl (0.1N) and dried at reduced pressure resulting 125.7 g of colourless liquid product. The 19F NMR analysis showed a total conversion (>99% by mol) of the CF2CH2OH groups to the correspondent aromatic derivative —CF2CH2OC6F5.

US10906999B2. Fluoroelastomer compositions (2021-02-02). SOLVAY SPECIALTY POLYMERS ITALY S.P.A. [IT]. Inventors: Marco Avataneo [IT], Liubov Chernysheva [IT], Ugo De Patto [IT].
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6

Analytical Standards for Environmental and Forensic Analysis

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Materials. HPLC-grade acetonitrile, water, hexafluorobenzene (99%) and chlorobenzene (99.9%), iodobenzene (>99%) and fluorobenzene (>99.5%) were obtained from Sigma-Aldrich (Buchs, Switzerland), and toluene (99.85%) and acetone (99.9%) from Acros Organics (Geel, Belgium). Analytical-grade pesticide and drug standards were purchased from Sigma-Aldrich, and were: ametryn, atrazine, prometon, prometryn, propazine, simazine, terbutryn, disulfoton, famphur, parathion, parathion-methyl, phorate, sulfotep, thionazin, triethyl thiophosphate, dimethoate, metolachlor, pyrimethanil, malathion, cyprodinil, flusilazole, cyproconazole, trifloxystrobin, quinoxyfen, tebuconazole, pyriproxyfen, pyridaben, difenoconazole, azoxystrobin, diazepam, cocaine, methadone, desipramine, imipramine, MDMA, ketamine, lidocaine and fentanyl. Phenanthrene-d10, pyrene-d10, and a polycyclic aromatic hydrocarbon mix (CRM 47930) were purchased from Sigma-Aldrich.
Mirabelli M.F, & Zenobi R. (2018). Solid-Phase Microextraction Coupled to Capillary Atmospheric Pressure Photoionization-Mass Spectrometry for Direct Analysis of Polar and Nonpolar Compounds. Analytical chemistry, 90(8).
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7

Copper-Catalyzed Azide-Alkyne Cycloaddition

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All chemicals were used as provided without further purification unless noted otherwise. Tetrahydrofuran, triethylamine, oxalyl chloride, propargyl amine, sodium ascorbate, neocuproine, hexa (ethylene glycol) dithiol, glycerol ethoxylate, PEG 600 diol and hexafluorobenzene were purchased from Sigma Aldrich. Deuterobenzene, deuterated dimethyl sulfoxide and deuterochloroform were purchased from Cambridge Isotope Laboratories (CIL). Copper(II) acetate was obtained from Acros Organics and 2,2-Dimethoxy-2-phenylacetophenone (DMPA) from TCI. TBTA was synthesized following a previously published procedure.43 Perfluorotripropylamine (FC 3283), methoxyperfluorobutane (HFE 7100), 2-(Trifluoromethyl)-3-ethoxydodecafluorohexane (HFE 7500) and Krytox FSH were obtained from Miller-Stephenson. Acetonitrile was obtained from EMD and hexafluoroisopropanol (HFIP) from Alfa-Aesar. Thiourea was purchased from Chem-Impex International and ethanol, methanol, sodium hydroxide and hydrochloric acid were obtained from Macron Fine Chemicals.
Scanga R., Chrastecka L., Mohammad R., Meadows A., Quan P.L, & Brouzes E. (2018). Click chemistry approaches to expand the repertoire of PEG-based fluorinated surfactants for droplet microfluidics. RSC Advances, 8(23), 12960-12974.
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8

Analytical Standards for Environmental Monitoring

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(R,S)-atenolol (≥98%), beta-estradiol (≥98%), pyrene (99%), tamoxifen (≥99%), salbutamol (≥96%), hexafluorobenzene (99%), HPLC-grade chlorobenzene (99.9%), methanol (≥99.9%), dichloromethane (≥99.5%), and trimethoprim (≥99%), as well as the EPA 8279 organophosphorous pesticide mix 2 (CRM47908: dimethoate, disulfoton, famphur, parathion, parathion-methyl, phorate, sulfotep, thionazin, and triethyl thiophosphate) were purchased from Sigma-Aldrich (Buchs, Switzerland).
Benzothiazole (>96%) and N,N-diethyl-meta-toluamide (>98%) were obtained from Tokyo Chemical Industry (Eschborn, Germany), 1H-benzotriazole (99%) from ABCR Chemicals (Karlsruhe, Germany), caffeine (≥99%), fluorobenzene (>99.5%), and toluene (>99.7%) from Fluka-Chemie AG (Neu-Ulm, Switzerland), carbamazepine (99%), hexane (96%), 1,2-dichlorobenzene (>99%) and acetone for residue analysis (99.9%) from Acros Organics (Geel, Belgium), sulfamethoxazole from Apollo Scientific Ltd (Stockport, UK), and HPLC grade acetonitrile from Fisher Scientific (Reinach, Switzerland). Chromatography grade LiChrosolv® water was used and purchased from VWR International GmbH (Dietikon, Switzerland).
Huba A.K., Mirabelli M.F, & Zenobi R. (2018). High-throughput screening of PAHs and polar trace contaminants in water matrices by direct solid-phase microextraction coupled to a dielectric barrier discharge ionization source. Analytica chimica acta, 1030.
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