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[ CAS No. 769-40-4 ] {[proInfo.proName]}

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Product Details of [ 769-40-4 ]

CAS No. :769-40-4 MDL No. :MFCD00004829
Formula : C6H2F4S Boiling Point : -
Linear Structure Formula :- InChI Key :IGOGJHYWSOZGAE-UHFFFAOYSA-N
M.W : 182.14 Pubchem ID :69859
Synonyms :

Calculated chemistry of [ 769-40-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 33.53
TPSA : 38.8 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.85
Log Po/w (XLOGP3) : 2.58
Log Po/w (WLOGP) : 4.21
Log Po/w (MLOGP) : 4.28
Log Po/w (SILICOS-IT) : 3.84
Consensus Log Po/w : 3.35

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.0
Solubility : 0.183 mg/ml ; 0.001 mol/l
Class : Soluble
Log S (Ali) : -3.04
Solubility : 0.165 mg/ml ; 0.000905 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.62
Solubility : 0.0433 mg/ml ; 0.000238 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.49

Safety of [ 769-40-4 ]

Signal Word:Danger Class:3,6.1
Precautionary Statements:P210-P233-P240-P241-P242-P243-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P303+P361+P353-P304-P304+P340-P305+P351+P338-P311-P312-P321-P322-P330-P332+P313-P337+P313-P340-P362-P363-P370+P378-P403-P403+P233-P403+P235-P405-P501 UN#:1992
Hazard Statements:H225-H302-H312-H315-H319-H331-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 769-40-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 769-40-4 ]

[ 769-40-4 ] Synthesis Path-Downstream   1~100

  • 2
  • [ 769-40-4 ]
  • [ 111873-88-2 ]
YieldReaction ConditionsOperation in experiment
95% With chlorine
  • 3
  • [ 769-40-4 ]
  • [ 75-03-6 ]
  • [ 78522-94-8 ]
YieldReaction ConditionsOperation in experiment
76% With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 0.333333h;
75% With copper(I) oxide In N,N-dimethyl acetamide at 70℃; for 20h;
  • 4
  • [ 769-40-4 ]
  • [ 106-95-6 ]
  • [ 78522-89-1 ]
YieldReaction ConditionsOperation in experiment
83% With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 0.333333h;
  • 5
  • [ 769-40-4 ]
  • [ 106-95-6 ]
  • [ 78522-96-0 ]
YieldReaction ConditionsOperation in experiment
71% With copper(l) iodide; n-butyllithium In tetrahydrofuran; hexane for 14.5h; Ambient temperature;
  • 6
  • [ 769-40-4 ]
  • [ 106-96-7 ]
  • 2,3,5,6-tetrafluorophenyl propargyl sulfide [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: 2,3,5,6-tetrafluorothiophenol With potassium carbonate In acetonitrile at 20℃; for 0.0833333h; Stage #2: propargyl bromide In toluene; acetonitrile at 50℃; 4.1.2 General procedure for the synthesis of alkynes 1-7 General procedure: A suspension of the corresponding thiophenol (10mmol) and anhydrous K2CO3 (21mmol, 2.90g) in MeCN (35mL) was stirred at room temperature for 5min. Propargyl bromide (15mmol, 1.67mL; 80% soln in toluene) was added dropwise and the resulting mixture was heated at 50°C for 3h. Quenching with H2O (10mL) and evaporation of organic volatiles under reduced pressure provided a solution, which was extracted with CH2Cl2 (2×10 mL). The organic extract was washed with brine (10mL), dried (Na2SO4) and evaporated at reduced pressure to afford a crude product, which was used without further purification in subsequent reactions. Analytically pure samples were obtained by flash column chromatography (silica gel; eluent: hexanes, then MeOH/CH2Cl2 5:95).
With potassium hydroxide In methanol for 12h; Ambient temperature; Yield given;
  • 7
  • [ 769-40-4 ]
  • [ 55520-67-7 ]
  • 2'-deoxy-5-<1-(2-methoxyphenylthio)ethyl>uridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With hydrogenchloride; 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol In water; acetonitrile at 80℃; for 1h;
  • 8
  • [ 327-54-8 ]
  • [ 769-40-4 ]
YieldReaction ConditionsOperation in experiment
(i) nBuLi, (ii) sulfur; Multistep reaction;
Stage #1: 1,2,4,5-Tetrafluorobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Schlenk technique; Inert atmosphere; Stage #2: With sulphur at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #3: With hydrogenchloride In water monomer at 0℃; for 0.166667h; Inert atmosphere; Schlenk technique;
  • 9
  • [ 10075-62-4 ]
  • [ 769-40-4 ]
  • 1,4-Dimethoxy-2-<(2,3,5,6-tetrafluorophenyl)thio>naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With bis-[(trifluoroacetoxy)iodo]benzene In various solvent(s) for 0.5h; Ambient temperature;
  • 10
  • [ 75-45-6 ]
  • [ 769-40-4 ]
  • 3-Difluoromethylsulfanyl-1,2,4,5-tetrafluoro-benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydroxide In 1,4-dioxane; water at 45℃; for 2.2h;
  • 11
  • [ 769-40-4 ]
  • [ 64317-34-6 ]
  • C19H2F13NS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetonitrile at 20℃; for 5h; Yield given;
  • 12
  • [ 769-40-4 ]
  • [ 71153-92-9 ]
  • 2,3,5,6-Tetrafluoro-N-(2,3,4,5,6-pentafluoro-phenyl)-4-(2,3,5,6-tetrafluoro-phenylsulfanyl)-benzimidoyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetonitrile at 20℃; for 22h;
  • 13
  • [ 769-40-4 ]
  • [ 87228-28-2 ]
  • N-(2,3,4,5,6-Pentafluoro-phenyl)-thiobenzimidic acid 2,3,5,6-tetrafluoro-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetonitrile at 20℃; for 22h;
  • 14
  • [ 769-40-4 ]
  • Methanesulfonic acid 2-{2-methoxy-6-nitro-4-[(2S,5S)-5-(3,4,5-trimethoxy-phenyl)-tetrahydro-furan-2-yl]-phenoxy}-ethyl ester [ No CAS ]
  • (2S,5S)-2-{3-Methoxy-5-nitro-4-[2-(2,3,5,6-tetrafluoro-phenylsulfanyl)-ethoxy]-phenyl}-5-(3,4,5-trimethoxy-phenyl)-tetrahydro-furan [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With triethylamine In ethanol for 16h; Heating;
  • 15
  • [ 22489-66-3 ]
  • [ 769-40-4 ]
  • (3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-9-methyl-6-methylene-3-(2,3,5,6-tetrafluoro-phenylsulfanylmethyl)-octahydro-azuleno[4,5-b]furan-2,8-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With triethylamine In methanol at 20℃; for 2h;
  • 17
  • [ 769-40-4 ]
  • [ 113543-35-4 ]
  • [ 300592-62-5 ]
YieldReaction ConditionsOperation in experiment
75% With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 1h;
  • 18
  • [ 1899-24-7 ]
  • [ 769-40-4 ]
  • 5-(2,3,5,6-tetrafluorobenzothiolate)-2-furfuraldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,3,5,6-tetrafluorothiophenol With sodium hydride In tetrahydrofuran Stage #2: 5-bromo-2-furancarboxaldehyde In tetrahydrofuran at 20℃; for 24h;
  • 19
  • [ 363-72-4 ]
  • [ 769-40-4 ]
YieldReaction ConditionsOperation in experiment
With potassium hydrosulfide In N,N-dimethyl-formamide at 45 - 55℃;
  • 20
  • [ 769-40-4 ]
  • [ 1559-88-2 ]
  • [ 344-04-7 ]
  • 21
  • [ 769-40-4 ]
  • [ 1835-61-6 ]
YieldReaction ConditionsOperation in experiment
93% With chlorine at 400℃; for 0.305h;
92% Stage #1: 2,3,5,6-tetrafluorothiophenol With phosphorus pentachloride at 198 - 200℃; for 5h; Sealed tube; Stage #2: With sodium carbonate In water for 4h; General procedure: Chlorination of polyfluoroarenes. Method 1. Polyfluoroarenethiol was charged in an ampule and PCl5 was added by portions. After the gas evolution finished the ampule was sealed, placed into a metal case, and heated. After the reaction completed the ampule was cooled, opened, its content was placed into a flask under a layer of water with ice (80-100 g), stirred for 2 h by magnetic stirrer to hydrolyze the phosphorus compounds, then alkalinized with Na2CO3, stirred for 2 h more, and subjected to steam distillation. The reaction product was separated, dried with CaCl2, and analyzed by GC and 19F NMR methods. Compounds 2, 6, 8, 10, 12, 15, 16, and 17 were obtained.
  • 22
  • [ 769-40-4 ]
  • [ 5055-11-8 ]
  • [ 864228-25-1 ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: (2-chloroethyl)diphenylphosphane With caesium carbonate In acetonitrile for 0.5h; Reflux; Stage #2: 2,3,5,6-tetrafluorothiophenol In acetonitrile for 19h; Reflux;
69% With caesium carbonate In acetonitrile for 16h; Heating;
With caesium carbonate In acetonitrile for 16h; Inert atmosphere; Reflux;
  • 23
  • [ 769-40-4 ]
  • [ 21988-87-4 ]
  • 1,3,5-Trimethyl-2,4,6-tris-(2,3,5,6-tetrafluoro-phenylsulfanylmethyl)-benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: 2,3,5,6-tetrafluorothiophenol With sodium ethanolate In ethanol for 0.25h; Stage #2: 1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene In ethanol for 24h; Heating;
  • 24
  • [ 769-40-4 ]
  • (R)-3-Methyl-2-(2,3,5,6-tetrafluoro-phenylsulfanyl)-butyraldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 75 percent / DBU / tetrahydrofuran / 1 h / 20 °C 2: 91 percent / LiBH4 / tetrahydrofuran; H2O / 3 h / 0 °C 3: oxalyl chloride; DMSO; DIPEA / CH2Cl2 / -78 - -50 °C
  • 25
  • [ 769-40-4 ]
  • [ 300592-72-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 75 percent / DBU / tetrahydrofuran / 1 h / 20 °C 2: 91 percent / LiBH4 / tetrahydrofuran; H2O / 3 h / 0 °C
  • 26
  • [ 769-40-4 ]
  • [ 300592-84-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 75 percent / DBU / tetrahydrofuran / 1 h / 20 °C 2: 91 percent / LiBH4 / tetrahydrofuran; H2O / 3 h / 0 °C 3: oxalyl chloride; DMSO; DIPEA / CH2Cl2 / -78 - -50 °C 4: 33 percent / diethyl ether; CH2Cl2 / 0.5 h / -78 °C
  • 27
  • [ 769-40-4 ]
  • [ 300592-94-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 75 percent / DBU / tetrahydrofuran / 1 h / 20 °C 2: 91 percent / LiBH4 / tetrahydrofuran; H2O / 3 h / 0 °C 3: oxalyl chloride; DMSO; DIPEA / CH2Cl2 / -78 - -50 °C 4: 28 percent / diethyl ether; CH2Cl2 / 0.5 h / -78 °C
  • 28
  • [ 769-40-4 ]
  • [(2S,3R)-3-(2,3,5,6-tetrafluorophenylthio)-4-methylpent-2-oxy]diphenylphosphine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 75 percent / DBU / tetrahydrofuran / 1 h / 20 °C 2.1: 91 percent / LiBH4 / tetrahydrofuran; H2O / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; DIPEA / CH2Cl2 / -78 - -50 °C 4.1: 33 percent / diethyl ether; CH2Cl2 / 0.5 h / -78 °C 5.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 5.2: 85 percent / tetrahydrofuran; hexane / 3 h / 20 °C
  • 29
  • [ 769-40-4 ]
  • [(2R,3R)-3-(2,3,5,6-tetrafluorophenylthio)-4-methylpent-2-oxy]diphenylphosphine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 75 percent / DBU / tetrahydrofuran / 1 h / 20 °C 2.1: 91 percent / LiBH4 / tetrahydrofuran; H2O / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; DIPEA / CH2Cl2 / -78 - -50 °C 4.1: 28 percent / diethyl ether; CH2Cl2 / 0.5 h / -78 °C 5.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 5.2: 80 percent / tetrahydrofuran; hexane / 3 h / 20 °C
  • 30
  • [ 769-40-4 ]
  • 3-Methoxy-2-[2-(2,3,5,6-tetrafluoro-phenylsulfanyl)-ethoxy]-5-[(2S,5S)-5-(3,4,5-trimethoxy-phenyl)-tetrahydro-furan-2-yl]-phenylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 88 percent / triethylamine / ethanol / 16 h / Heating 2: 69.3 percent / Zn, CaCl2 / ethanol / 16 h / Heating
  • 31
  • [ 769-40-4 ]
  • (+/-)-trans-2-[3-methoxy-4-(2,3,5,6-tetrafluorophenylthioethoxy)-5-(N-butyl-N-hydroxyureidyl)phenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 88 percent / triethylamine / ethanol / 16 h / Heating 2: 69.3 percent / Zn, CaCl2 / ethanol / 16 h / Heating 3: 1.) triethylamine / 1.) CH2Cl2, reflux, 2 h, 2.) CH2Cl2, RT, overnight
  • 32
  • [ 769-40-4 ]
  • (+/-)-trans-2-[3-methoxy-4-(2,3,5,6-tetrafluorophenylsulfonylethoxy)-5-(N-butyl-N-hydroxyureidyl)phenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 88 percent / triethylamine / ethanol / 16 h / Heating 2: 69.3 percent / Zn, CaCl2 / ethanol / 16 h / Heating 3: 1.) triethylamine / 1.) CH2Cl2, reflux, 2 h, 2.) CH2Cl2, RT, overnight 4: 63 percent / aq. magnesium monoperoxyphthalic acid / acetonitrile / 2 h / Ambient temperature
  • 33
  • [ 769-40-4 ]
  • 2,5-Dimethyl-3-(2,3,5,6-tetrafluoro-phenylsulfanyl)-thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / chlorine 2: 21 percent / SnCl4 / diethyl ether / Heating
  • 34
  • [ 769-40-4 ]
  • 1-Methyl-2,4-bis-(2,3,5,6-tetrafluoro-phenylsulfanyl)-1H-pyrrole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / chlorine 2: SnCl4 / diethyl ether / Heating
  • 35
  • [ 769-40-4 ]
  • 1-Methyl-2,5-bis-(2,3,5,6-tetrafluoro-phenylsulfanyl)-1H-pyrrole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / chlorine 2: SnCl4 / diethyl ether / Heating
  • 36
  • [ 58832-36-3 ]
  • [ 769-40-4 ]
  • [ 1317-39-1 ]
  • 5-(2,3,5,6-tetrafluorophenylthio)furan-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N-methyl-acetamide; EXAMPLE 26 5-(2,3,5,6-Tetrafluorophenylthio)furan-3-carboxylic Acid In an open flask, cuprous oxide (1.95 g., 13.7 mmoles) was combined with 2,3,5,6-tetrafluorothiophenol (5.0 g., 27.4 mmoles) in 40 ml. of dimethylformamide and heated at 140 C. for 2 hours. The reaction was cooled, 5-bromofuran-3-carboxylic acid (2.62 g., 13.7 mmoles) in 50 ml. of dimethylformamide was added, the reaction mixture refluxed for 2 hours, and product (2.75 g.) isolated according to the procedure of Example 9. Recrystallization from methanol/water gave purified 5-(2,3,5,6-tetrafluorophenylthio)furan-3-carboxylic acid (1.78 g., m.p. 150-153 C., m/e 292). Analysis: Calcd. for C11 H4 O3 SF4: C, 45.21; H, 1.37. Found: C, 45.18; H, 1.61.
  • 37
  • [ 769-40-4 ]
  • [ 301-04-2 ]
  • Pb(p-SC6HF4)2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water
In ethanol; water at 20℃; Pb(SRF)2 General procedure: All lead thiolates were prepared by modification of previously publishedmethods [32-36]: To a solution of Pb(CH3COO)2 (5.2 mmol) in 100 mL water, thiol (HSRF) (10.0 mmol)dissolved in about 10 mL of ethanol was added under vigorous stirring at room temperature. A white oryellow precipitate was rapidly formed. The solid was filtrated and washed 3x with 50 mL methanol and 3x with 25 mL hexane. Caution: Lead derivatives are extremely toxic and must be handled followingthe proper security procedures. Thiols and thiolates are odorous; consequently, all procedures must becompleted in a fume hood. IR spectra of the lead thiolates are available in the SI.
In methanol; water
  • 38
  • [ 29786-93-4 ]
  • [ 124-38-9 ]
  • [ 769-40-4 ]
  • [ 5211-44-9 ]
YieldReaction ConditionsOperation in experiment
76.5% In diethyl ether; hexane at -70°C after acidification with 6 N HCl;
In diethyl ether; hexane
  • 39
  • [ 10025-99-7 ]
  • [ 769-40-4 ]
  • K2{Pt(p-SC6HF4)4} [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% In water addn. of HSC6HF4 (20 mmol) to aq. soln. of K2(PtCl4) (2.4 mmol); stirring for 1 h;; distg. off solvent; crystn. from ethanol; elem. anal.;;
  • 40
  • [ 65814-72-4 ]
  • [ 769-40-4 ]
  • [ 149830-13-7 ]
YieldReaction ConditionsOperation in experiment
81% In dichloromethane byproducts: H2O; 40 min at room temp.; concn. in vac., chromy. (silica, CH2Cl2), recrystn. (CH2Cl2/heptane); elem. anal.;
  • 41
  • {Os(meso-tetra-p-tolylporphyrinate)}2BF4 [ No CAS ]
  • [ 769-40-4 ]
  • [ 149830-22-8 ]
YieldReaction ConditionsOperation in experiment
72% With pyridine In pyridine stirred for 25 min; stripped to dryness, recrystn. (CH2Cl2/hexane);
  • 42
  • (K-18-crown-6) bis(nitro){α,α,alpha.,α-meso-tetrakis-(o-pivalamidophenyl)porphinato}iron(III) [ No CAS ]
  • [ 769-40-4 ]
  • K(1+)*C12H24O6*NO2(1-)*Fe(NO){C64H64N8O4}*0.5C6H5Cl={K(NO2)C12H24O6}{Fe(NO){C64H64N8O4}}*0.5C6H5Cl [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In chlorobenzene addn. of 2,3,5,6-tetrafluorothiophenol to a soln. of Fe-compd., change pf color from deep red to light red; crystn. of single cystals upon slow diffusion of pentane into the chlorobenzene soln., washing (H2O), washing (dry pentane);
  • 43
  • [ 20816-12-0 ]
  • [ 769-40-4 ]
  • [Os(SC6F4H)4(P(C6H5)3)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With P(C6H5)3 In ethanol under N2, no rigorous exclusion of air; addn. of S-compd. in EtOH to a soln. of OsO4 in EtOH, addn. of PPh3 in EtOH and refluxing of mixt. for ca 12 h; pptn. on cooling, filtering off, washing with cold EtOH and cold hexane, column chromy. (silica gel, hexane/CHCl3), recrystn. by slow evapn. ofsolvent; elem. anal.;
  • 44
  • [(η5-C5Me5)Ru(NO)Cl2] [ No CAS ]
  • [ 769-40-4 ]
  • [(η5-C5Me5)Ru(NO)(SC6F4H)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With NaOMe In tetrahydrofuran; methanol under N2 atm. to soln. (Cp*Ru(NO)Cl2) in THF was added MeOH soln. C6F4HSH and NaOMe and stirred at room temp. for 2 h; solvent was pumped off, residue was extd. with CH2Cl2 and crystd. from CH2Cl2/hexane; elem. anal.;
  • 45
  • [ 226949-47-9 ]
  • [ 769-40-4 ]
  • [ 226949-54-8 ]
YieldReaction ConditionsOperation in experiment
82% In acetone (N2); stirring (1h, 25°C); solvent redn. (vac.), filtering; elem. anal.;
  • 46
  • [ 59246-46-7 ]
  • [ 769-40-4 ]
  • [ 226949-51-5 ]
YieldReaction ConditionsOperation in experiment
78% In acetone (N2); stirring (1 h, 25°C); solvent redn. (vac.), filtering; elem. anal.;
  • 47
  • gold(III) tetrachloride trihydrate [ No CAS ]
  • tetraethylammonium chloride hydrate [ No CAS ]
  • [ 769-40-4 ]
  • [ 1092372-33-2 ]
YieldReaction ConditionsOperation in experiment
70% In ethanol; water byproducts: HCl; (in air) thiol was added dropwise to a soln. of HAuCl4*3H2O in ethanol, then (C2H5)4NCl in water was added; cooled at -20°C for several days, decanted, ppt. was washed with water and ether, dried in air;
  • 48
  • [ 29892-37-3 ]
  • tetraethylammonium chloride hydrate [ No CAS ]
  • [ 769-40-4 ]
  • [ 1092372-36-5 ]
YieldReaction ConditionsOperation in experiment
71% With potassium hydroxide In methanol (in air) thiol was added to a soln. of KOH in methanol, the soln. was added dropwise over a period of 2-3 min to a suspn. of Au-complex in methanol, stirred for 1 h, filtered, (C2H5)4NCl was added to the filtrate; the solvent was removed in vac., the solid was washed with water and dried in air; elem. anal.;
  • 49
  • [ 31643-49-9 ]
  • [ 769-40-4 ]
  • [ 1224844-29-4 ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate In N,N-dimethyl-formamide at 30 - 40℃; for 49.5h; Inert atmosphere;
  • 50
  • [ 769-40-4 ]
  • [ 1217086-83-3 ]
YieldReaction ConditionsOperation in experiment
80% With sulfuric acid; hydrogen bromide; nitric acid at 75 - 80℃;
  • 51
  • [ 104413-90-3 ]
  • [ 769-40-4 ]
  • [ 1233221-21-0 ]
YieldReaction ConditionsOperation in experiment
56% With N(C2H5)3 In dichloromethane stirred for 24 h at room temp. under Ar atm.; evapd.; column chromy.; recrystd. (CHCl3/methanol); elem. anal.;
  • 52
  • [ 1232686-04-2 ]
  • [ 769-40-4 ]
  • [ 1232686-72-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: ethyl 5-(aminosulfonyl)-2-chloronicotinate; 2,3,5,6-tetrafluorothiophenol With caesium carbonate In dimethyl sulfoxide at 50 - 90℃; Stage #2: With hydrogenchloride In water
  • 53
  • [ 1232686-68-8 ]
  • [ 769-40-4 ]
  • C18H12F4N4O3S2*0.05ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% Stage #1: 5-(aminosulfonyl)-2-chloro-N-(pyridin-2-ylmethyl)nicotinamide; 2,3,5,6-tetrafluorothiophenol With caesium carbonate In dimethyl sulfoxide at 50 - 90℃; Stage #2: With hydrogenchloride In water
  • 54
  • [ 40741-46-6 ]
  • [ 769-40-4 ]
  • C11H6F4N2O2S2*0.4ClH [ No CAS ]
  • 55
  • [ 769-40-4 ]
  • [ 1175523-38-2 ]
  • 3,4-dichloro-2,4-dinitro-1,1-bis(2,3,5,6-tetrafluorophenylthio)buta-1,3-diene [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With sodium ethanolate In ethanol at 0℃; for 2h;
  • 56
  • [ 769-40-4 ]
  • [ 1393488-73-7 ]
  • 3,4-dichloro-2,4-dinitro-1,1-bis(2,3,5,6-tetrafluorophenylthio)buta-1,3-diene [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With sodium ethanolate In ethanol at 0℃; for 2h;
  • 57
  • [ 14871-92-2 ]
  • [ 769-40-4 ]
  • [(2,2'-bipyridine)PdCl(SC6F4H-4)] [ No CAS ]
  • 58
  • [ 14871-92-2 ]
  • [ 769-40-4 ]
  • [(2,2'-bipyridine)Pd(SC6F4H-4)2] [ No CAS ]
  • 59
  • [ 14783-10-9 ]
  • [ 769-40-4 ]
  • [(1,10-phenanthroline)Pd(SC6F4H-4)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With potassium <i>tert</i>-butylate In ethanol at 20℃; for 4h; Schlenk technique; Inert atmosphere; Darkness;
  • 60
  • [ 769-40-4 ]
  • [ 488706-26-9 ]
  • [ 489427-21-6 ]
YieldReaction ConditionsOperation in experiment
110 mg Stage #1: C22H43N5O5 With 4-methyl-morpholine; HATU In N,N-dimethyl-formamide for 0.0833333h; Stage #2: 2,3,5,6-tetrafluorothiophenol In N,N-dimethyl-formamide for 0.166667h; 4.b b) Synthesis of Chelator 1A-TFTP Ester b) Synthesis of Chelator 1A-TFTP Ester [0168] [0169] To Chelator 1A (from Step a; 300 mg, 0.66 mmol) in DMF (2 ml) was added HATU (249 mg, 0.66 mmol) and NMM (132 μL, 1.32 mmol). The mixture was stirred for 5 minutes then tetrafluorothiophenol (0.66 mmol, 119 mg) was added. The solution was stirred for 10 minutes then the reaction mixture was diluted with 20% acetonitrile/water (8 ml) and the product purified by RP-HPLC yielding 110 mg of the desired product following freeze-drying.
  • 61
  • [ 769-40-4 ]
  • [ 1600-27-7 ]
  • C12H2F8HgS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In water for 2h; Inert atmosphere; 4.2 Preparation of [Hg(SC6H4(CF3)-2)2] 7 General procedure: A mixture of Hg(OOCCH3)2 (318mg, 1.0mmol) and HSC6H4(CF3)-2 (0.356g, 2.0mmol) in 30mL of distilled and deoxygenated water was magnetically stirred during 2h. The solution was initially clear but it slowly became cloudy with the formation of a white precipitate. After the solution was cooled at 0°C for 1h, the colorless crystalline solid was filtered, washed with cold water and air dried to yield 510mg (88%) of [Hg(SC6H4(CF3)-2)2] 7 as a white crystalline solid. Colorless crystals suitable for X-ray studies were grown from an acetone solution by slow evaporation of the solvent.
  • 62
  • [ 14568-13-9 ]
  • [ 769-40-4 ]
  • cis-[(DMSO)2Pt(SC6F4H-4)2] [ No CAS ]
  • trans-[(DMSO)2Pt(SC6F4H-4)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate In acetone for 0.5h; Inert atmosphere; (I) Attempted preparation of [(DMSO)2Pt(SC6F4H-4)2] 120 mg (0.28 mmol) [(DMSO)2PtCl2], 110 mg (0.60 mmol) HSC6F4H-4 and 68 mg (0.60 mmol) KOtBu were dissolved in 100 mL of acetone and stirred at ambient temperature. After 30 min a small volume was separated and evaporated to dryness. 1H and 19F NMR spectra in [D6]acetone and CDCl3 revealed the presence of cis- and trans-[(DMSO)2Pt(SC6F4H-4)2]: 1H NMR ([D6]acetone) cis: d = 7.68 (m,2H, H4), 3.57 (s, 6H, CH3, 3JPt-H = 22 Hz); trans: d = 7.68 (m, 2H,H4), 2.61 (s, 6H, CH3, 3JPt-H = 51 Hz) ppm. 1H NMR (CDCl3) cis: d = 7.12 (m, 2H, H4), 3.56 (s, 6H, 3JPt-H = 22 Hz, CH3); trans: d = 7.12 (m, 2H, H4), 2.64 (s, 6H, 3J Pt-H = 50 Hz, CH3) ppm. 19FNMR ([D6]acetone) cis and trans: d = 135.4 (m, 4F, F2,6), 140.3 (m, 4F, F3,5). After three hours stirring the mixture was filtered over Celite and the filtrate was evaporated to dryness leaving an orange solid which turned out to be virtually insoluble in most organic solvent. Elemental analysis, MS and IR spectroscopy revealed that this solid was polymeric [Pt(SC6F4H-4)2]m. C12H2F8-PtS2 (557.34): Calc. C, 25.86; H, 0.36; S, 11.51. Found: C, 25.91;H, 0.44; S, 11.41%. IR spectrum (pellet) of the product showed no bands for (DMSO)Pt (e.g., mSO 1120-1150 cm1) but typical signals for the thiolate ligand at ~m 3069 (vw), 1629 (w), 1490(vs), 1435 (s), 1367 (s), 1249 (w), 1229 (s), 1175 (s), 1130 (w), 918 (vs), 880 (s), 851 (s) and 712 (s) cm1 which were very similar to those reported recently for the Pd derivative [Pt(SC6F4H-4)2]m[38]. EI-MS: m/z = 362 [4-HF4C6S-SC6F4H-4]+, 330 [4-HF4C6-SC6F4H-4]+, 182 [HSC6F4H-4]+. In the filtrate of the reaction mixture,DMSO was found (NMR). The solid can be partially re-dissolved in[D6]DMSO giving 1H and 19F NMR signals corresponding to [(DMSO)2Pt(SC6F4H-4)2]: 1H NMR ([D6]DMSO) cis: d = 7.79 (m,2H, H4), 3.74 (s, 6H, 3JPt-H = 22 Hz, CH3); trans: d = 7.79 (m, 2H,H4), 2.73 (s, 6H, 3JPt-H = 51 Hz, CH3) ppm. 19F NMR ([D6]DMSO) cis and trans: d = 133.2 (m, 4F, F2,6), 140.0 (m, 4F, F3,5).
  • 63
  • [ 14568-13-9 ]
  • [ 1232394-32-9 ]
  • [ 769-40-4 ]
  • [(11-trifluoromethyldipyrido[3,2-a:2',3'-c]phenazine)Pt(perfluoro thiophenolate)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With potassium <i>tert</i>-butylate In acetone for 2h; Inert atmosphere; (F) Reaction of two equivalent of HSC6F4H-4 and KOtBu with[(DMSO)2PtCl2] and bpy, dppz, and CF3dppz General procedure: All three reactions gave excellent yields of 86% for bpy, 85% for dppz, and 90% for CF3-dppz after 2 h reaction time.
  • 64
  • [ 19535-47-8 ]
  • [ 75992-73-3 ]
  • [ 769-40-4 ]
  • [(dipyrido[3,2-a:2',3'-c]phenazine)Pt(SC6F4H-4)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With potassium tert-butylate; In acetone; for 2h;Inert atmosphere; General procedure: All three reactions gave excellent yields of 86% for bpy, 85% for dppz, and 90% for CF3-dppz after 2 h reaction time.
85% With potassium tert-butylate; In acetone; at 24.84℃; for 2h; General procedure: Reaction of two equivalent of HSC6F4H-4 and KOtBu with[(DMSO)2PtCl2] and bpy, dppz, and CF3dppz: All three reactionsgave excellent yields of 86% for bpy, 85% for dppz, and 90% for CF3-dppz after 2 h reaction time.
  • 65
  • chloromethyl(1,5-cyclooctadiene)platinum(II) [ No CAS ]
  • [ 769-40-4 ]
  • [(cycloocta-1,5-diene)Pt(Me)(SC6F4H-4)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With potassium <i>tert</i>-butylate In acetone for 2h; Inert atmosphere; (B) Reaction of one equivalent of HSC6F4H-4 with [(COD)PtCl2], [(COD)Pt(Me)Cl] or [(COD)Pt(Bn)Cl] General procedure: In the presence of a small amount of KOtBu the reaction proceeded smoothly and was complete after 2 h. The products containing Me (yield:82%) or Bn (yield: 85%) coligands were yellow. The faint yellow monosubstituted complex [(COD)Pt(SC6F4H-4)Cl] was obtained in 85% yield.
82% With potassium <i>tert</i>-butylate In acetone at 20℃; for 2h; (A) Reaction of two equivalents of HSC6F4H-4 with[(COD)PtCl2]: General procedure: In a first attempt an amount of 200 mg (0.534 mmol)[(COD)PtCl2] and 200 mg (1.1 mmol) HSC6F4H-4 was stirred in20 mL of acetone at ambient temperature. NMR monitoringshowed the intermediate formation of the mono-substituted complex[(COD)Pt(SC6F4H-4)Cl]. After two days >99% conversion to thedisubstituted complex was determined. After workup, 300 mg(0.45 mmol = 84%) of faint yellow [(COD)Pt(SC6F4H-4)2] wereobtained. Addition of small amounts (0.2 eq) of KOtBu accelerated the reaction markedly and a reaction time of 1.5 h was sufficient(yield: 95%).
82% With potassium <i>tert</i>-butylate In acetone at 20℃; for 2h; General procedure: The Pt precursors [(COD)PtCl2], [(COD)Pt(Me)Cl], [(COD)Pt(Bn)Cl], [(bpy)PtCl2],[(dppz)PtCl2], cis-[(PPh3)2PtCl2], [(dppe)PtCl2], [(dppb)Pt(C6F5)Cl],and [(DMSO)2PtCl2] (ca. 1 mmol) were dissolved in about 50 mL of acetone and one or two equivalents of HSC6F4H-4 + KOtBu or KSC6F4H-4 were added. After stirring at ambient temperature for the required time, the mixture was filtered over Celite to remove traces of elemental Pt, precipitated KCl or other undissolved material and the filtrate was evaporated to dryness. The residues were carefully recrystallised from acetone or CH2Cl2 to yield the products as microcrystalline material. Four modifications (A-D) were applied.
  • 66
  • [ 51177-67-4 ]
  • [ 769-40-4 ]
  • [(COD)Pt(Bn)(SC6F4H-4)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With potassium <i>tert</i>-butylate In acetone for 2h; Inert atmosphere; (B) Reaction of one equivalent of HSC6F4H-4 with [(COD)PtCl2], [(COD)Pt(Me)Cl] or [(COD)Pt(Bn)Cl] General procedure: In the presence of a small amount of KOtBu the reaction proceeded smoothly and was complete after 2 h. The products containing Me (yield:82%) or Bn (yield: 85%) coligands were yellow. The faint yellow monosubstituted complex [(COD)Pt(SC6F4H-4)Cl] was obtained in 85% yield.
85% With potassium <i>tert</i>-butylate In acetone at 20℃; for 2h; (A) Reaction of two equivalents of HSC6F4H-4 with[(COD)PtCl2]: General procedure: In a first attempt an amount of 200 mg (0.534 mmol)[(COD)PtCl2] and 200 mg (1.1 mmol) HSC6F4H-4 was stirred in20 mL of acetone at ambient temperature. NMR monitoringshowed the intermediate formation of the mono-substituted complex[(COD)Pt(SC6F4H-4)Cl]. After two days >99% conversion to thedisubstituted complex was determined. After workup, 300 mg(0.45 mmol = 84%) of faint yellow [(COD)Pt(SC6F4H-4)2] wereobtained. Addition of small amounts (0.2 eq) of KOtBu accelerated the reaction markedly and a reaction time of 1.5 h was sufficient(yield: 95%).
85% With potassium <i>tert</i>-butylate In acetone at 20℃; for 2h; General procedure: The Pt precursors [(COD)PtCl2], [(COD)Pt(Me)Cl], [(COD)Pt(Bn)Cl], [(bpy)PtCl2],[(dppz)PtCl2], cis-[(PPh3)2PtCl2], [(dppe)PtCl2], [(dppb)Pt(C6F5)Cl],and [(DMSO)2PtCl2] (ca. 1 mmol) were dissolved in about 50 mL of acetone and one or two equivalents of HSC6F4H-4 + KOtBu or KSC6F4H-4 were added. After stirring at ambient temperature for the required time, the mixture was filtered over Celite to remove traces of elemental Pt, precipitated KCl or other undissolved material and the filtrate was evaporated to dryness. The residues were carefully recrystallised from acetone or CH2Cl2 to yield the products as microcrystalline material. Four modifications (A-D) were applied.
  • 67
  • [ 14647-25-7 ]
  • [ 769-40-4 ]
  • [ 515843-01-3 ]
YieldReaction ConditionsOperation in experiment
83% With potassium <i>tert</i>-butylate In acetone for 5h; Inert atmosphere; (C) Reaction of two equivalents of HSC6F4H-4 and KOtBu with[(dppe)PtCl2], cis-[(PPh3)2PtCl2], [(bpy)PtCl2], and [(dppz)PtCl2] General procedure: These reactions required the presence of two equivalents of KOtBu. Conversion to the red phosphine complexes proceeded smoothly within 5 h with yields, accounting to 83% for dppe, and 90% for PPh3, while the red bpy and dppz complexes formed very slowly and, after 3 days stirring at 298 K and workup we obtained 43% yield for bpy and 38% for dppz.
83% With potassium <i>tert</i>-butylate In acetone at 20℃; for 5h; (A) Reaction of two equivalents of HSC6F4H-4 with[(COD)PtCl2]: General procedure: In a first attempt an amount of 200 mg (0.534 mmol)[(COD)PtCl2] and 200 mg (1.1 mmol) HSC6F4H-4 was stirred in20 mL of acetone at ambient temperature. NMR monitoringshowed the intermediate formation of the mono-substituted complex[(COD)Pt(SC6F4H-4)Cl]. After two days >99% conversion to thedisubstituted complex was determined. After workup, 300 mg(0.45 mmol = 84%) of faint yellow [(COD)Pt(SC6F4H-4)2] wereobtained. Addition of small amounts (0.2 eq) of KOtBu accelerated the reaction markedly and a reaction time of 1.5 h was sufficient(yield: 95%).
83% With potassium <i>tert</i>-butylate In acetone at 20℃; for 5h; General procedure: The Pt precursors [(COD)PtCl2], [(COD)Pt(Me)Cl], [(COD)Pt(Bn)Cl], [(bpy)PtCl2],[(dppz)PtCl2], cis-[(PPh3)2PtCl2], [(dppe)PtCl2], [(dppb)Pt(C6F5)Cl],and [(DMSO)2PtCl2] (ca. 1 mmol) were dissolved in about 50 mL of acetone and one or two equivalents of HSC6F4H-4 + KOtBu or KSC6F4H-4 were added. After stirring at ambient temperature for the required time, the mixture was filtered over Celite to remove traces of elemental Pt, precipitated KCl or other undissolved material and the filtrate was evaporated to dryness. The residues were carefully recrystallised from acetone or CH2Cl2 to yield the products as microcrystalline material. Four modifications (A-D) were applied.
  • 68
  • [ 15604-36-1 ]
  • [ 769-40-4 ]
  • [ 936011-53-9 ]
YieldReaction ConditionsOperation in experiment
90% With potassium tert-butylate; In acetone; for 5h;Inert atmosphere; General procedure: These reactions required the presence of two equivalents of KOtBu. Conversion to the red phosphine complexes proceeded smoothly within 5 h with yields, accounting to 83% for dppe, and 90% for PPh3, while the red bpy and dppz complexes formed very slowly and, after 3 days stirring at 298 K and workup we obtained 43% yield for bpy and 38% for dppz.
90% With potassium tert-butylate; In acetone; at 20℃; for 5h; General procedure: In a first attempt an amount of 200 mg (0.534 mmol)[(COD)PtCl2] and 200 mg (1.1 mmol) HSC6F4H-4 was stirred in20 mL of acetone at ambient temperature. NMR monitoringshowed the intermediate formation of the mono-substituted complex[(COD)Pt(SC6F4H-4)Cl]. After two days >99% conversion to thedisubstituted complex was determined. After workup, 300 mg(0.45 mmol = 84%) of faint yellow [(COD)Pt(SC6F4H-4)2] wereobtained. Addition of small amounts (0.2 eq) of KOtBu accelerated the reaction markedly and a reaction time of 1.5 h was sufficient(yield: 95%).
90% With potassium tert-butylate; In acetone; at 20℃; for 5h; General procedure: The Pt precursors [(COD)PtCl2], [(COD)Pt(Me)Cl], [(COD)Pt(Bn)Cl], [(bpy)PtCl2],[(dppz)PtCl2], cis-[(PPh3)2PtCl2], [(dppe)PtCl2], [(dppb)Pt(C6F5)Cl],and [(DMSO)2PtCl2] (ca. 1 mmol) were dissolved in about 50 mL of acetone and one or two equivalents of HSC6F4H-4 + KOtBu or KSC6F4H-4 were added. After stirring at ambient temperature for the required time, the mixture was filtered over Celite to remove traces of elemental Pt, precipitated KCl or other undissolved material and the filtrate was evaporated to dryness. The residues were carefully recrystallised from acetone or CH2Cl2 to yield the products as microcrystalline material. Four modifications (A-D) were applied.
  • 69
  • [ 12080-32-9 ]
  • [ 769-40-4 ]
  • [(cycloocta-1,5-diene)PtCl(SC6F4H-4)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With potassium tert-butylate; In acetone; for 2h;Inert atmosphere; General procedure: In the presence of a small amount of KOtBu the reaction proceeded smoothly and was complete after 2 h. The products containing Me (yield:82%) or Bn (yield: 85%) coligands were yellow. The faint yellow monosubstituted complex [(COD)Pt(SC6F4H-4)Cl] was obtained in 85% yield
85% With potassium tert-butylate; In acetone; at 20℃; General procedure: The Pt precursors [(COD)PtCl2], [(COD)Pt(Me)Cl], [(COD)Pt(Bn)Cl], [(bpy)PtCl2],[(dppz)PtCl2], cis-[(PPh3)2PtCl2], [(dppe)PtCl2], [(dppb)Pt(C6F5)Cl],and [(DMSO)2PtCl2] (ca. 1 mmol) were dissolved in about 50 mL of acetone and one or two equivalents of HSC6F4H-4 + KOtBu or KSC6F4H-4 were added. After stirring at ambient temperature for the required time, the mixture was filtered over Celite to remove traces of elemental Pt, precipitated KCl or other undissolved material and the filtrate was evaporated to dryness. The residues were carefully recrystallised from acetone or CH2Cl2 to yield the products as microcrystalline material. Four modifications (A-D) were applied.
  • 70
  • [ 366-18-7 ]
  • [ 10025-99-7 ]
  • [ 769-40-4 ]
  • [(2,2'-bipyridine)Pt(SC6F4H-4)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With potassium <i>tert</i>-butylate In acetone at 24.84℃; for 72h; (A) Reaction of two equivalents of HSC6F4H-4 with[(COD)PtCl2]: General procedure: In a first attempt an amount of 200 mg (0.534 mmol)[(COD)PtCl2] and 200 mg (1.1 mmol) HSC6F4H-4 was stirred in20 mL of acetone at ambient temperature. NMR monitoringshowed the intermediate formation of the mono-substituted complex[(COD)Pt(SC6F4H-4)Cl]. After two days >99% conversion to thedisubstituted complex was determined. After workup, 300 mg(0.45 mmol = 84%) of faint yellow [(COD)Pt(SC6F4H-4)2] wereobtained. Addition of small amounts (0.2 eq) of KOtBu accelerated the reaction markedly and a reaction time of 1.5 h was sufficient(yield: 95%).
51% With potassium <i>tert</i>-butylate In methanol; water; acetic acid for 72h; General procedure: (E) Reaction of two equivalents of HSC6F4H-4 and KOtBu withK2PtCl4 and bpy, dppz, and CF3dppz: The reaction were carriedout in acetone:MeOH:H2O 1:1:1 mixture and gave yields of 51%for bpy, 55% for dppz, and 58% for CF3dppz after 3 d reaction time.
  • 71
  • [ 10025-99-7 ]
  • [ 19535-47-8 ]
  • [ 769-40-4 ]
  • [(dipyrido[3,2-a:2',3'-c]phenazine)Pt(SC6F4H-4)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With potassium tert-butylate; In acetone; at 24.84℃; for 72h; General procedure: In a first attempt an amount of 200 mg (0.534 mmol)[(COD)PtCl2] and 200 mg (1.1 mmol) HSC6F4H-4 was stirred in20 mL of acetone at ambient temperature. NMR monitoringshowed the intermediate formation of the mono-substituted complex[(COD)Pt(SC6F4H-4)Cl]. After two days >99% conversion to thedisubstituted complex was determined. After workup, 300 mg(0.45 mmol = 84%) of faint yellow [(COD)Pt(SC6F4H-4)2] wereobtained. Addition of small amounts (0.2 eq) of KOtBu accelerated the reaction markedly and a reaction time of 1.5 h was sufficient(yield: 95%).
55% With potassium tert-butylate; In methanol; water; acetone; for 72h; General procedure: (E) Reaction of two equivalents of HSC6F4H-4 and KOtBu withK2PtCl4 and bpy, dppz, and CF3dppz: The reaction were carriedout in acetone:MeOH:H2O 1:1:1 mixture and gave yields of 51%for bpy, 55% for dppz, and 58% for CF3dppz after 3 d reaction time.
  • 72
  • [ 10025-99-7 ]
  • [ 1232394-32-9 ]
  • [ 769-40-4 ]
  • [(11-trifluoromethyldipyrido[3,2-a:2',3'-c]phenazine)Pt(perfluoro thiophenolate)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With potassium <i>tert</i>-butylate In acetone at 24.84℃; for 72h; (A) Reaction of two equivalents of HSC6F4H-4 with[(COD)PtCl2]: General procedure: In a first attempt an amount of 200 mg (0.534 mmol)[(COD)PtCl2] and 200 mg (1.1 mmol) HSC6F4H-4 was stirred in20 mL of acetone at ambient temperature. NMR monitoringshowed the intermediate formation of the mono-substituted complex[(COD)Pt(SC6F4H-4)Cl]. After two days >99% conversion to thedisubstituted complex was determined. After workup, 300 mg(0.45 mmol = 84%) of faint yellow [(COD)Pt(SC6F4H-4)2] wereobtained. Addition of small amounts (0.2 eq) of KOtBu accelerated the reaction markedly and a reaction time of 1.5 h was sufficient(yield: 95%).
58% With potassium <i>tert</i>-butylate In methanol; water; acetone for 72h; General procedure: (E) Reaction of two equivalents of HSC6F4H-4 and KOtBu withK2PtCl4 and bpy, dppz, and CF3dppz: The reaction were carriedout in acetone:MeOH:H2O 1:1:1 mixture and gave yields of 51%for bpy, 55% for dppz, and 58% for CF3dppz after 3 d reaction time.
  • 73
  • [ 208119-01-1 ]
  • [ 769-40-4 ]
  • [(dipyrido[3,2-a:2',3'-c]phenazine)Pt(SC6F4H-4)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With potassium <i>tert</i>-butylate In acetone at 24.84℃; for 72h; (A) Reaction of two equivalents of HSC6F4H-4 with[(COD)PtCl2]: General procedure: In a first attempt an amount of 200 mg (0.534 mmol)[(COD)PtCl2] and 200 mg (1.1 mmol) HSC6F4H-4 was stirred in20 mL of acetone at ambient temperature. NMR monitoringshowed the intermediate formation of the mono-substituted complex[(COD)Pt(SC6F4H-4)Cl]. After two days >99% conversion to thedisubstituted complex was determined. After workup, 300 mg(0.45 mmol = 84%) of faint yellow [(COD)Pt(SC6F4H-4)2] wereobtained. Addition of small amounts (0.2 eq) of KOtBu accelerated the reaction markedly and a reaction time of 1.5 h was sufficient(yield: 95%).
38% With potassium <i>tert</i>-butylate In acetone at 24.84℃; for 72h; General procedure: The Pt precursors [(COD)PtCl2], [(COD)Pt(Me)Cl], [(COD)Pt(Bn)Cl], [(bpy)PtCl2],[(dppz)PtCl2], cis-[(PPh3)2PtCl2], [(dppe)PtCl2], [(dppb)Pt(C6F5)Cl],and [(DMSO)2PtCl2] (ca. 1 mmol) were dissolved in about 50 mL of acetone and one or two equivalents of HSC6F4H-4 + KOtBu or KSC6F4H-4 were added. After stirring at ambient temperature for the required time, the mixture was filtered over Celite to remove traces of elemental Pt, precipitated KCl or other undissolved material and the filtrate was evaporated to dryness. The residues were carefully recrystallised from acetone or CH2Cl2 to yield the products as microcrystalline material. Four modifications (A-D) were applied.
  • 74
  • [ 13965-31-6 ]
  • [ 769-40-4 ]
  • [(2,2'-bipyridine)Pt(SC6F4H-4)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With potassium tert-butylate; In acetone; at 24.84℃; for 72h; General procedure: In a first attempt an amount of 200 mg (0.534 mmol)[(COD)PtCl2] and 200 mg (1.1 mmol) HSC6F4H-4 was stirred in20 mL of acetone at ambient temperature. NMR monitoringshowed the intermediate formation of the mono-substituted complex[(COD)Pt(SC6F4H-4)Cl]. After two days >99% conversion to thedisubstituted complex was determined. After workup, 300 mg(0.45 mmol = 84%) of faint yellow [(COD)Pt(SC6F4H-4)2] wereobtained. Addition of small amounts (0.2 eq) of KOtBu accelerated the reaction markedly and a reaction time of 1.5 h was sufficient(yield: 95%).
43% With potassium tert-butylate; In acetone; at 20℃; for 72h; General procedure: The Pt precursors [(COD)PtCl2], [(COD)Pt(Me)Cl], [(COD)Pt(Bn)Cl], [(bpy)PtCl2],[(dppz)PtCl2], cis-[(PPh3)2PtCl2], [(dppe)PtCl2], [(dppb)Pt(C6F5)Cl],and [(DMSO)2PtCl2] (ca. 1 mmol) were dissolved in about 50 mL of acetone and one or two equivalents of HSC6F4H-4 + KOtBu or KSC6F4H-4 were added. After stirring at ambient temperature for the required time, the mixture was filtered over Celite to remove traces of elemental Pt, precipitated KCl or other undissolved material and the filtrate was evaporated to dryness. The residues were carefully recrystallised from acetone or CH2Cl2 to yield the products as microcrystalline material. Four modifications (A-D) were applied.
  • 75
  • [ 875766-01-1 ]
  • [ 769-40-4 ]
  • [(1,4-bis(diphenylphosphino)butane)Pt(C6F5)(SC6F4H-4)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium <i>tert</i>-butylate In acetone at 24.84℃; for 3h; (A) Reaction of two equivalents of HSC6F4H-4 with[(COD)PtCl2]: General procedure: In a first attempt an amount of 200 mg (0.534 mmol)[(COD)PtCl2] and 200 mg (1.1 mmol) HSC6F4H-4 was stirred in20 mL of acetone at ambient temperature. NMR monitoringshowed the intermediate formation of the mono-substituted complex[(COD)Pt(SC6F4H-4)Cl]. After two days >99% conversion to thedisubstituted complex was determined. After workup, 300 mg(0.45 mmol = 84%) of faint yellow [(COD)Pt(SC6F4H-4)2] wereobtained. Addition of small amounts (0.2 eq) of KOtBu accelerated the reaction markedly and a reaction time of 1.5 h was sufficient(yield: 95%).
78% With potassium <i>tert</i>-butylate In acetone at 20℃; for 3h; The Pt precursors [(COD)PtCl2], [(COD)Pt(Me)Cl], [(COD)Pt(Bn)Cl], [(bpy)PtCl2],[(dppz)PtCl2], cis-[(PPh3)2PtCl2], [(dppe)PtCl2], [(dppb)Pt(C6F5)Cl],and [(DMSO)2PtCl2] (ca. 1 mmol) were dissolved in about 50 mL of acetone and one or two equivalents of HSC6F4H-4 + KOtBu or KSC6F4H-4 were added. After stirring at ambient temperature for the required time, the mixture was filtered over Celite to remove traces of elemental Pt, precipitated KCl or other undissolved material and the filtrate was evaporated to dryness. The residues were carefully recrystallised from acetone or CH2Cl2 to yield the products as microcrystalline material. Four modifications (A-D) were applied.
  • 76
  • [ 12080-32-9 ]
  • [ 769-40-4 ]
  • [(cycloocta-1,5-diene)Pt(SC6F4H-4)2] [ No CAS ]
  • [(cycloocta-1,5-diene)PtCl(SC6F4H-4)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With potassium tert-butylate; In acetone; at 20℃; for 1.5h; General procedure: In a first attempt an amount of 200 mg (0.534 mmol)[(COD)PtCl2] and 200 mg (1.1 mmol) HSC6F4H-4 was stirred in20 mL of acetone at ambient temperature. NMR monitoringshowed the intermediate formation of the mono-substituted complex[(COD)Pt(SC6F4H-4)Cl]. After two days >99% conversion to thedisubstituted complex was determined. After workup, 300 mg(0.45 mmol = 84%) of faint yellow [(COD)Pt(SC6F4H-4)2] wereobtained. Addition of small amounts (0.2 eq) of KOtBu accelerated the reaction markedly and a reaction time of 1.5 h was sufficient(yield: 95%).
  • 77
  • [ 19535-47-8 ]
  • dichlorobis(dimethyl sulfoxide)platinum(II) [ No CAS ]
  • [ 769-40-4 ]
  • [(dipyrido[3,2-a:2',3'-c]phenazine)Pt(SC6F4H-4)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With potassium tert-butylate; In acetone; at 24.84℃; for 2h; General procedure: In a first attempt an amount of 200 mg (0.534 mmol)[(COD)PtCl2] and 200 mg (1.1 mmol) HSC6F4H-4 was stirred in20 mL of acetone at ambient temperature. NMR monitoringshowed the intermediate formation of the mono-substituted complex[(COD)Pt(SC6F4H-4)Cl]. After two days >99% conversion to thedisubstituted complex was determined. After workup, 300 mg(0.45 mmol = 84%) of faint yellow [(COD)Pt(SC6F4H-4)2] wereobtained. Addition of small amounts (0.2 eq) of KOtBu accelerated the reaction markedly and a reaction time of 1.5 h was sufficient(yield: 95%).
  • 78
  • [ 366-18-7 ]
  • dichlorobis(dimethyl sulfoxide)platinum(II) [ No CAS ]
  • [ 769-40-4 ]
  • [(2,2'-bipyridine)Pt(SC6F4H-4)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With potassium <i>tert</i>-butylate In acetone at 24.84℃; for 2h; (A) Reaction of two equivalents of HSC6F4H-4 with[(COD)PtCl2]: General procedure: In a first attempt an amount of 200 mg (0.534 mmol)[(COD)PtCl2] and 200 mg (1.1 mmol) HSC6F4H-4 was stirred in20 mL of acetone at ambient temperature. NMR monitoringshowed the intermediate formation of the mono-substituted complex[(COD)Pt(SC6F4H-4)Cl]. After two days >99% conversion to thedisubstituted complex was determined. After workup, 300 mg(0.45 mmol = 84%) of faint yellow [(COD)Pt(SC6F4H-4)2] wereobtained. Addition of small amounts (0.2 eq) of KOtBu accelerated the reaction markedly and a reaction time of 1.5 h was sufficient(yield: 95%).
  • 79
  • dichlorobis(dimethyl sulfoxide)platinum(II) [ No CAS ]
  • [ 769-40-4 ]
  • [(DMSO)2Pt(SC6F4H-4)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate In acetone at 20℃; for 0.5h;
  • 80
  • dichlorobis(dimethyl sulfoxide)platinum(II) [ No CAS ]
  • [ 1232394-32-9 ]
  • [ 769-40-4 ]
  • [(11-trifluoromethyldipyrido[3,2-a:2',3'-c]phenazine)Pt(perfluoro thiophenolate)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With potassium <i>tert</i>-butylate In acetone at 24.84℃; for 2h; (A) Reaction of two equivalents of HSC6F4H-4 with[(COD)PtCl2]: General procedure: In a first attempt an amount of 200 mg (0.534 mmol)[(COD)PtCl2] and 200 mg (1.1 mmol) HSC6F4H-4 was stirred in20 mL of acetone at ambient temperature. NMR monitoringshowed the intermediate formation of the mono-substituted complex[(COD)Pt(SC6F4H-4)Cl]. After two days >99% conversion to thedisubstituted complex was determined. After workup, 300 mg(0.45 mmol = 84%) of faint yellow [(COD)Pt(SC6F4H-4)2] wereobtained. Addition of small amounts (0.2 eq) of KOtBu accelerated the reaction markedly and a reaction time of 1.5 h was sufficient(yield: 95%).
  • 81
  • [ 366-18-7 ]
  • [ 14568-13-9 ]
  • [ 769-40-4 ]
  • [(2,2'-bipyridine)Pt(SC6F4H-4)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With potassium <i>tert</i>-butylate In acetone at 24.84℃; for 2h; General procedure: Reaction of two equivalent of HSC6F4H-4 and KOtBu with[(DMSO)2PtCl2] and bpy, dppz, and CF3dppz: All three reactionsgave excellent yields of 86% for bpy, 85% for dppz, and 90% for CF3-dppz after 2 h reaction time.
  • 82
  • [ 14568-13-9 ]
  • [ 1232394-32-9 ]
  • [ 769-40-4 ]
  • [(2,2'-bipyridine)Pt(SC6F4H-4)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With potassium <i>tert</i>-butylate In acetone at 24.84℃; for 2h; General procedure: Reaction of two equivalent of HSC6F4H-4 and KOtBu with[(DMSO)2PtCl2] and bpy, dppz, and CF3dppz: All three reactionsgave excellent yields of 86% for bpy, 85% for dppz, and 90% for CF3-dppz after 2 h reaction time.
  • 83
  • [ 14568-13-9 ]
  • [ 769-40-4 ]
  • cis-[(DMSO)2Pt(SC6F4H-4)2] [ No CAS ]
  • 2C6HF4S(1-)*2C2H6OS*Pt(2+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate In acetone at 20℃; for 0.5h; 120 mg(0.28 mmol) [(DMSO)2PtCl2], 110 mg (0.60 mmol) HSC6F4H-4 and68 mg (0.60 mmol) KOtBu were dissolved in 100 mL of acetone and stirred at ambient temperature. After 30 min a small volume was separated and evaporated to dryness. 1H and 19F NMR spectrai n [D6]acetone and CDCl3 revealed the presence of cis- and trans-[(DMSO)2Pt(SC6F4H-4)2]: 1H NMR ([D6]acetone) cis: d = 7.68 (m,2H, H4), 3.57 (s, 6H, CH3, 3JPt-H = 22 Hz); trans: d = 7.68 (m, 2H,H4), 2.61 (s, 6H, CH3, 3JPt-H = 51 Hz) ppm. 1H NMR (CDCl3) cis:d = 7.12 (m, 2H, H4), 3.56 (s, 6H, 3JPt-H = 22 Hz, CH3); trans:d = 7.12 (m, 2H, H4), 2.64 (s, 6H, 3JPt-H = 50 Hz, CH3) ppm. 19FNMR ([D6]acetone) cis and trans: d = 135.4 (m, 4F, F2,6), 140.3(m, 4F, F3,5).
  • 84
  • [ 14568-13-9 ]
  • [ 769-40-4 ]
  • [Pt(SC6F4H-4)2]m [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate In acetone at 20℃; for 3h; 120 mg(0.28 mmol) [(DMSO)2PtCl2], 110 mg (0.60 mmol) HSC6F4H-4 and68 mg (0.60 mmol) KOtBu were dissolved in 100 mL of acetone and stirred at ambient temperature. After three hours stirring the mixture was filtered over Celite and the filtrate was evaporated to dryness leaving an orange solid which turned out to be virtually insoluble in most organic solvent. Elemental analysis, MS and IR spectroscopy revealed that this solid was polymeric [Pt(SC6F4H-4)2]m. C12H2F8-PtS2 (557.34): Calc. C, 25.86; H, 0.36; S, 11.51. Found: C, 25.91;H, 0.44; S, 11.41%. IR spectrum (pellet) of the product showed no bands for (DMSO)Pt (e.g., mSO 1120-1150 cm1) but typical signals for the thiolate ligand at ~m 3069 (vw), 1629 (w), 1490(vs), 1435 (s), 1367 (s), 1249 (w), 1229 (s), 1175 (s), 1130 (w),918 (vs), 880 (s), 851 (s) and 712 (s) cm1 which were very similar to those reported recently for the Pd derivative [Pt(SC6F4H-4)2]m[38]. EI-MS: m/z = 362 [4-HF4C6S-SC6F4H-4]+, 330 [4-HF4C6-SC6F4H-4]+, 182 [HSC6F4H-4]+. In the filtrate of the reaction mixture,DMSO was found (NMR).
  • 85
  • [ 91-01-0 ]
  • [ 769-40-4 ]
  • benzhydryl-(2,3,5,6-tetrafluorophenyl)sulfane [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 120℃; for 16h; Sealed tube; Green chemistry;
  • 86
  • [ 769-40-4 ]
  • [ 778-34-7 ]
  • 1,2,4,5-tetrafluoro-3-[(2,3,5,6-tetrafluorophenyl)sulfanyl]-6-(trichloromethyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With potassium carbonate In N,N-dimethyl-formamide at 22℃; for 5h; 1,2,4,5-Tetrafluoro-3-[(2,3,5,6-tetrafluorophenyl)sulfanyl]-6-(trichloromethyl)benzene (14). A mixture of 0.24 g (1.29 mmol) of thiol 1a, 0.38 g (1.30 mmol) of compound 12, and 0.18 g (1.30 mmol) of K2CO3 in 2.0 mL of DMF was stirred for 5 h at 22°C and treated as described above. Yield 0.47 g (1.05 mmol) (81%).Light yellow liquid. IR spectrum, ν, cm-1: 3082, 1632,1495, 1470, 1441, 1383, 1281, 1236, 1178, 1132,1045, 985, 922, 825, 783, 727, 714, 702. 1H NMRspectrum, δ, ppm: 7.16 t.t (JH-F3',5' 9, JH-F2',6' 7 Hz). 19FNMR spectrum, δ, ppm: 25.3 m (2F3',5'), 29.0 m (2F),29.1 m (2F), 29.6 m (2F). Found [M]+ 445.8735.C13HCl3F8S. Calculated [M]+ 445.8731.
  • 87
  • [ 67-66-3 ]
  • [ 769-40-4 ]
  • tris-(2,3,5,6-tetrafluorophenylsulfanyl)methane [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With sodium hydroxide In 1,4-dioxane; water at 48 - 53℃; for 14h; Reaction of thiol (1) with CHCl3. In DMF. The reaction mixture obtained from 1.02 g (5.60 mmol) of thiol 1a, 0.23 g (1.93 mmol) of CHCl3 in 2.0 mL of DMF, and 0.76 g (5.51 mmol) of K2CO3 after 14 days at room temperature contained thiol 1a and 1,2,4,5-tetrafluorobenzene 5a [20] in the ratio 92 : 8 (19F NMR spectrum).In 1,4-dioxane. From 3.05 g (16.76 mmol) of thiol 1,2.97 g (24.87 mmol) of CHCl3, 6.95 g (173.75 mmol) of NaOH in solution of 17 mL of 1,4-dioxane and 10 mL of water (14 h, 48-53°C) a mixture was obtained containing according data thiol 1a, tris-(2,3,5,6-tetrafluorophenylsulfanyl)methane 4, and arene 5 in a ratio8 : 89 : 3 (19F, 1H NMR). To the reaction mixture conc. HCl was added, the products were extracted with CHCl3, the organic layer was separated, washed with water and 10% solution of Na2CO3. The solvent and arene 5a were distilled off on a rotary evaporator. Yield of tris(2,3,5,6-tetrafluorophenylsulfanyl)methane (4) 2.45 g (4.40 mmol) (79%). Colorless crystals, mp 92-94° (EtOH). IR spectrum, ν, cm-1: 3083, 1633,1608, 1493, 1436, 1377, 1235, 1179, 1128, 917, 893,862, 850, 760, 734, 712. UV spectrum, λmax, nm (log ε):215 (4.45), 275 (4.18). 1H NMR spectrum, δ, ppm:6.89 s (1H, Csp3H), 7.21 m (3Harom). 19F NMR spectrum,δ, ppm: 25.1 m (2F3,5), 29.6 m (2F2,6). Mass spectrum, m/z (Irel, %): 556 (0.1) [M]+, 377 (12) [M + 2 - C6HF4S]+,376 (20) [M + 1 - C6HF4S]+, 375 (100) [M - C6HF4S]+,194 (26) [M - C12H2F8S2]+, 193 (35) [M - C12H3F8S2]+,181 (11) [M - C13H3F8S2]. Found, %: C 40.94; H 0.80;F 41.06; S 17.45. [M - C6HF4S]+ 374.9541. C13H3F8S2.Calculated, %: C 41.01; H 0.72; F 40.97; S 17.29. [M -C6HF4S]+ 374.9520. XRD analysis. Orthorhombic system, space group Pna21. C19H4F12S3, M 556.40, a 9.9472(4), b 12.7033(5),c 16.4762(6) Å, V 2082.0(1) Å3, Z 4, dcalc 1.775 g/cm3.4600 independent reflections (θmax 27.1°), among them 3706 observed reflections. Final refinement parameters R 0.0383, S 1.064. The ellip-soids of one tetrafluorophenyl group are strongly elongated. An attempt was done of disordering this group by two positions. This led to a small decrease (0.0018) in theR-factor, but the ellipsoids remained strongly extended. (CCDC 1405718).
  • 88
  • [ 75-25-2 ]
  • [ 769-40-4 ]
  • tris-(2,3,5,6-tetrafluorophenylsulfanyl)methane [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With sodium hydroxide In 1,4-dioxane; water at 60 - 70℃; for 8h; Reaction of thiol (1a) with CHBr3. The reaction mixture obtained from 1.60 g (8.79 mmol) of thiol 1,4.53 g (17.93 mmol) of CHBr3, and 3.64 g (91.00 mmol) of NaOH in 12 mL of 1,4-dioxane and 9 mL of water (60-70°C, 8 h) contained compounds 4 and 5a in a ratio 95 : 5 (19F NMR). After adding 5% HCl solution till pH < 1 the separated precipitate of compound 4 was filtered off and dried in air. We obtained 1.15 g (2.07 mmol) of compound 4a, yield 70%.
  • 89
  • [ 75-43-4 ]
  • [ 769-40-4 ]
  • fluorochloromethyl (2,3,5,6-tetrafluorophenyl)sulfide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With sodium hydroxide In 1,4-dioxane; water at 55℃; for 6h; Reaction of thiol (1a) with fluorodichloromethane(6). The flow of compound 6 was passed for 6 h at 55°C through a mixture of 22.05 g (121.15 mmol) of thiol 1a and 23.05 g (576.25 mmol) of NaOH in 160 mL of 1,4-dioxane and 132 mL of water. Then conc. HCl was added till pH < 1, and the mixture was subjected to steam distillation. We obtained 24.40 g of a mixture containing (GLC) 17% of initial thiol 1a, 65% ofsulfide 7a, and 3% of arene 5a. Yield of sulfide 7 inthe mixture 53%, 65% calculated on reacted thiol 1a,65%. Sulfide 7a was isolated by vacuum distillation. Fluorochloromethyl (2,3,5,6-tetrafluorophenyl)sulfide (7a). Colorless liquid, bp 85° (12-14 mmHg). 1H NMR spectrum, δ, ppm: 7.1 d (1H, JH-Fα 55 Hz), 7.2m (1Harom). 19F NMR spectrum, δ, ppm: 25.2 m (2F3,5),31.0 m (2F2,6), 59.2 d (1Fα, JFα-H 55 Hz). Found,%: C33.76; H 0.84; Cl 14.07; F 37.88; S 12.75. [M]+247.9488. 7H2ClF5S. Calculated, %: C 33.82; H 0.81;Cl 14.26; F 38.21; S 12.90. [M]+ 247.9486.
  • 90
  • [ 75-09-2 ]
  • [ 769-40-4 ]
  • [ 62601-14-3 ]
  • bis(2,3,5,6-tetrafluorophenylsulfanyl)methane [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 168h; Reactions of thiol (1) with dichloromethane, compounds (11 and 12), and of thiol (1b) with compound (15). General procedure: To a solution of the reagent in DMF in the presence of potassium carbonate thiol 1a or 1b was added. The reaction mixture that turned yellow-green[7] was stirred with a magnetic stirrer at 20°C,observing a gradual disappearance of the coloration. On the completion of the reaction the mixture was poured into a 5-fold greater volume of 5% HCl solution. The organic product was separated and purified by crystallization from EtOH (2, 13, and 16)or by sublimation in a vacuum (14). Bis(2,3,5,6-tetrafluorophenylsulfanyl)methane (2). From 1.97 g (10.82 mmol) of thiol 1a, 0.46 g (5.41 mmol) of dichloromethane, and 1.53 g (11.09 mmol) of K2CO3 in 10.0 mL of DMF after 7 days 1.90 g (5.05 mmol) of compound 2 was obtained. Yield 93%. Colorless crystals. Purity 99.8% (GLC), mp 62-64°C (EtOH). IR spectrum, ν, cm-1: 3109, 3082, 1630, 1616, 1493,1435, 1379, 1232, 1176, 918, 847, 710. UV spectrum, λmax, nm (log ε): 209 (4.20), 277 (4.02). 1H NMR spectrum, δ,ppm: 4.42 s (2H), 7.16 t.t (2Harom, JH-F3,59.5, JH-F2,6 7.2 Hz). 19F NMR spectrum, δ, ppm: 24.2 m(4F3,3',5,5'), 28.5 m (4F2,2',6,6'). Mass spectrum, m/z (Irel,%): 376 (8) [M]+, 195 (100) [M - HC6F4S]+, 181 (4)[M - HC6F4SCH2]+, 163 (4) [M - C6HF4S2]+, 137 (6)[M - C8H3F4S2]+. Found, %: C 41.45; H 1.06; F 40.60;S 16.90. [M]+ 375.9621. C13H4F8S2. Calculated, %: C41.49; H 1.07; F 40.39; S 17.04. [M]+ 375.9621. XRD analysis. Monoclinic system, space group P21/. C13H4F8S2, M 376.28, a 14.8264(9), b 5.2109(3),c 18.032(1) Å, β 90.736(2)°, V 1393.0(2) Å3, Z 4, dcalc .1.794 g/cm3. 3595 independent reflections (θmax28.7°), among them 2786 observed reflections. Final refinement parameters R 0.0394, S 0.984 (CCDC1405717).
  • 91
  • [ 769-40-4 ]
  • [ 327-54-8 ]
YieldReaction ConditionsOperation in experiment
With chloroform; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 336h; Reaction of thiol (1) with CHCl3. In DMF. The reaction mixture obtained from 1.02 g (5.60 mmol) of thiol 1a, 0.23 g (1.93 mmol) of CHCl3 in 2.0 mL of DMF, and 0.76 g (5.51 mmol) of K2CO3 after 14 days at room temperature contained thiol 1a and 1,2,4,5-tetrafluorobenzene 5a [20] in the ratio 92 : 8 (19F NMR spectrum).
  • 92
  • [ 652-30-2 ]
  • [ 769-40-4 ]
  • 1-(dichloromethyl)-2,3,5,6-tetrafluoro-4-[(2,3,5,6-tetrafluorophenyl)sulfanyl]benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate In N,N-dimethyl-formamide at 22℃; for 5h; 1-(Dichloromethyl)-2,3,5,6-tetrafluoro-4-[(2,3,5,6-tetrafluorophenyl)sulfanyl]benzene (13). The reaction mixture obtained from 0.21 g (1.15 mmol) of thiol 1a, 0.29 g (1.16 mmol) of benzyl chloride 11, and 0.17g (1.23 mmol) of K2CO3 in 2.0 mL of DMF was stirred for 5 h at 22°C and treated as described above. Yield 0.37 g (0.90 mmol) (78%). Colorless crystals, mp 40-42°C (EtOH). Purity 97% (GC-MS). IR spectrum, ν,cm-1: 3087, 1631, 1495, 1481, 1441, 1398, 1381, 1311,1281, 1236, 1219, 1178, 1128, 1055, 968, 920, 893,849, 775, 712, 602. UV spectrum, λmax, nm (log ε): 203(4.19), 287 (3.79). 1H NMR spectrum, δ, ppm: 6.92 s (1H,CHCl2), 7.14m (1H, Harom). 19F NMR spectrum, δ, ppm:22.4 m (2F3,5), 25.2 m (2F3',5'), 29.3-29.5 m (4F2,2',6,6').Mass spectrum, m/z (Irel, %): 414 (14) [M + 2]+, 412(19) [M]+, 379 (35) [M + 2 - Cl]+, 378 (14) [M + 1 -Cl]+, 377 (100) [M - Cl]+, 228 (10), 188 (8), 161 (8).Found, %: C 37.58; H 0.41; Cl 16.96; F 37.08; S 7.75.[M]+ 411.9117. C13H2Cl2F8S. Calculated, %: C 37.80;H 0.49; Cl 17.16; F 36.79; S 7.76. [M]+ 411.9121.
  • 93
  • [ 109-65-9 ]
  • [ 769-40-4 ]
  • butyl(2,3,5,6-tetrafluorophenyl)sulfane [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate In acetonitrile at 50℃; for 5h; Inert atmosphere;
  • 94
  • [ 108-77-0 ]
  • [ 769-40-4 ]
  • 2,4,6-tris((2,3,5,6-tetrafluorophenyl)thio)-1,3,5-triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With N-ethyl-N,N-diisopropylamine In acetone at 0℃; Schlenk technique; Inert atmosphere; Reflux;
  • 95
  • [ 622-97-9 ]
  • [ 769-40-4 ]
  • (4-methylphenethyl)(2,3,5,6-tetrafluorophenyl)sulfane [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With 1,8-diazabicyclo[5.4.0]undec-7-ene; N-fluorobis(benzenesulfon)imide In toluene at 20℃; Schlenk technique; Inert atmosphere;
  • 96
  • [ 769-40-4 ]
  • [ 1765-40-8 ]
  • 2,3,4,5,6-pentafluorobenzyl 2,3,5,6-tetrafluorophenyl sulfide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In ethanol at 20℃; for 2h; General procedure: Sulfides 1a-9a were synthesized on a 6 mmol scale by addingthe commercially available thiols to an ethanol solution of thecorresponding benzyl or phenacyl bromides in the presence ofpotassium carbonate as the basic reagent [28,38]. The mixture wasreacted for 2 h at room temperature. Usual work up gave a crudemixture that was purified by distillation. Usually, distilled sulfidessolidify on standing.
  • 97
  • [ 769-40-4 ]
  • 1-azido-3,6,9,12,15-pentaoxaoctadecan-18-oic acid [ No CAS ]
  • C19H25F4N3O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-azido-3,6,9,12,15-pentaoxaoctadecan-18-oic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.00833333h; Stage #2: 2,3,5,6-tetrafluorothiophenol In N,N-dimethyl-formamide at 20℃; for 1h; 1 N3-PEG5-(CH2)2-COOH 30mg (89uM), pyBOP 44mg (85uM) andN,N5 diisopropylethylamine 30uL (173uM) were dissolved in DMF (0.5mL) and shaken for 30sec.To the resulting solution 2,3,5,6-tetrathiophenol 7.6mg(42uM) was added and allowed to stir for lhr at RT. The crude mixture was purified by RP-HPLC.
  • 98
  • [ 769-40-4 ]
  • [ 651-80-9 ]
  • [ 367-23-7 ]
YieldReaction ConditionsOperation in experiment
1: 90% 2: 10% With water; triethylphosphine In 1,4-dioxane at 120℃; for 4h; Schlenk technique; Inert atmosphere; Glovebox;
  • 99
  • [ 769-40-4 ]
  • C20H39N5O5 [ No CAS ]
  • C26H39F4N5O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
110 mg Stage #1: C20H39N5O5 With 4-methyl-morpholine; HATU In N,N-dimethyl-formamide for 0.0833333h; Stage #2: 2,3,5,6-tetrafluorothiophenol In N,N-dimethyl-formamide for 0.166667h; 4.4b (Step 4b) Synthesis of Chelator 1A. To [Chelator 1]-glutaric acid (from Step 4a; 300 mg, 0.66 mmol) in DMF (2 ml) was added HATU (249 mg, 0.66 mmol) and NMM (132 μL, 1.32 mmol). The mixture was stirred for 5 minutes then tetrafluorothiophenol (0.66 mmol, 119 mg) was added. The solution was stirred for 10 minutes then the reaction mixture was diluted with 20% acetonitrile/water (8 ml) and the product purified by RP-HPLC yielding 110 mg of the desired product following freeze-drying.
  • 100
  • [ 939-16-2 ]
  • [ 769-40-4 ]
  • 3-((2,3,5,6-tetrafluorophenyl)thio)-2-quinolone [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 120℃; for 16h; Inert atmosphere; Schlenk technique;
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