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CAS No. : | 17763-80-3 | MDL No. : | MFCD00192354 |
Formula : | C7H4F3NO5S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NDTIXHNCNLKURN-UHFFFAOYSA-N |
M.W : | 271.17 | Pubchem ID : | 549870 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 3261 |
Hazard Statements: | H314 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 48% 2: 30% | With potassium phosphate In 1,4-dioxane at 85℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | In acetonitrile at 100℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | In acetonitrile for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 8% 2: 10% 3: 86% | With bis-triphenylphosphine-palladium(II) chloride; lithium chloride In tetrahydrofuran; N,N-dimethyl-formamide at 80℃; for 22h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate In N,N-dimethyl-formamide for 1.5h; Ambient temperature; | |
90% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h; | |
88% | With 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene on polystyrene.HL In acetonitrile at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene on polystyrene.HL In acetonitrile at 80℃; | |
92% | With potassium carbonate In N,N-dimethyl-formamide for 1h; Ambient temperature; | |
92% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 86% 2: 8% 3: 10% | With lithium chloride In tetrahydrofuran; N,N-dimethyl-formamide at 80℃; for 22h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With caesium carbonate In N,N-dimethyl-formamide at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; bis(pinacol)diborane In 1,4-dioxane at 80℃; for 14h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane for 7h; Heating; | |
92% | With N-ethyl-N,N-diisopropylamine In 1,4-dioxane for 7h; Heating / reflux; | |
With i-Pr2NEt | 19 Production of 4-nitrophenyl phenyl sulfide: Example 19 Production of 4-nitrophenyl phenyl sulfide: Heating and refluxing time: 7 hours. Aryl sulfonate and its amount used: 4-Nitrobenzene trifluoromethanesulfonate (542 mg, 2 mmol). Thiol compound and its amount used: Thiophenol (205 μL, 2 mmol). Amount of Pd2(dba)3 used: 46 mg, 0.05 mmol. Amount of Xantphos used: 58 mg, 0.1 mmol. Base and its amount used: i-Pr2NEt (700 μL, 4 mmol). Amount of 1,4-dioxane used: 10.8 mL. Property, yield and yield percentage of 4-nitrophenyl phenyl sulfide: Pale yellow solid; yield 425 mg; yield percentage 92 %. Development solvent in flash column chromatography: Hexane/ethyl acetate = 10/1. Melting point: 54°C-55°C. 1H NMR (CDCl3, 500 MHz) δ ppm: 8.06 (dt, 2H, J = 2.0 Hz, 7.0 Hz), 7.53-7.55 (m, 2H), 7.46 (d, 2H, J = 2.4 Hz), 7.45 (d, 1H, J = 1.0 Hz), 7.18 (dt, 2H, J = 2.0 Hz, 7.0 Hz). 13C NMR (CDCl3, 125 MHz) δ ppm: 148.90, 145.78, 135.15, 130.88, 130.44, 130.07, 127.11, 124.44. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 56% 2: 34% | With caesium carbonate; triphenylphosphine In toluene at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With palladium diacetate In ethanol at 95℃; for 0.25h; microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With caesium carbonate;palladium diacetate; tris-(o-tolyl)phosphine; In 1,4-dioxane; water; at 95℃; for 4h; | To a mixture of 4-nitrophenyl trifluoromethanesulfonate (30 mg, 0.11 mmol) and 1,4-dioxane (3 ml) were added water (0.3 ml), cesium carbonate (0.11 g, 0.34 mmol), <strong>[910251-11-5]potassium methoxymethyltrifluoroborate</strong> (17 mg, 0.11 mmol), palladium (II) acetate (1.3 mg, 0.0056 mmol) and tri-o-tolylphosphine (8.5 mg, 0.028 mmol). Then, the reaction mixture was stirred at 95C (external temperature) for 4 hours. After the reaction mixture was cooled at room temperature, water and heptane were added to the mixture, and the organic layer was separated. The organic layer was filtered, and the solvent was distilled off under reduced pressure. The residue was purified by NH-silica gel column chromatography (heptane:ethyl acetate=10:1) to obtain the title compound (13 mg, 0.078 mmol, 68%). 1H-NMR Spectrum (CDCl3) delta (ppm) : 3.45 (3H, s), 4. 56 (2H, s), 7.50 (2H, d, J=9.0Hz), 8.21(2H, d, J=8.8Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With potassium phosphate; triphenylphosphine In N,N-dimethyl-formamide at 90℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 3h; | XV. C C. 4-[(1-Ethylpropylamino)-methyl]-2-hydroxybenzonitrile SCHEME 43 Vanillin 4-Formyl-2-methoxyphenyl trifluoromethanesulfonate [0275] To a solution of vanillin (500 mg, 3.286 mmol) in DMF (10 mL) at room temp, was added potassium carbonate (908 mg, 6,572 mmol) and 4- nitrophenyl trifluoromethanesulfonate (1, 34g, 4,929 mmol) and the reaction mixture was stirred for 3h. Et20 was added to the reaction mixture and the organic layer was washed 3 times with water, dried, filtered and concentrated. The crude compound was then purified by flash chromatography (ethyl acetate-hexanes/1 : 9 to 3: 7) to provide sulfonate (880 mg, 94%). 1H RMN (400 MHz, CDC13) 8 : 4.03 (s, 3H), 7.44 (d, J= 8. 2 Hz, 1H), 7.54 (dd, lH, J= 1. 7 and 8.2 Hz), 7.59 (d, 1H, J= 1. 7 Hz), 10.02 (s, 1H). |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h; | A To a solution of vanillin (20.0 g, 131 mmol) in DMF (200 mL) at room temperature was added potassium carbonate (36 g, 263 mmol) and 4-nitrophenyl trifluoromethanesulfonate (54.0 g, 197 mmol) and the reaction mixture was stirred for 8 h. EtOAc (600 mL) was added to the reaction mixture and the organic layer was washed three times with water, dried, filtered, and concentrated. The crude compound was then purified by flash chromatography (ethylacetate/hexanes 1 :9 → 3:7) to provide 4-formyl~2-methoxyphenyl trifluoromethanesulfonate..H NMR (CDCI3, 500 MHz) δ 10.02 (s, IH), 7.60 (s, IH), 7.55 (d, J= 8.1 Hz, IH), 7.45 (d, J = 8.0 Hz, IH)5 4.04 (s, 3H); LC/MS (IE, m/z) 284.98 [M + I]+; tR = 3.31 min | |
With potassium carbonate In N,N-dimethyl-formamide for 8h; | 28.A Step A: 4-Formyl-2-methoxyphenyl trifluoromethanesulfonate Step A: 4-Formyl-2-methoxyphenyl trifluoromethanesulfonate: To a solution of vanillin (20 g,131 mmol) in DMF (200 mL) at room temperature was added potassium carbonate (36.30 g, 263 mmol) and 4-nitrophenyl trifluoromethanesulfonate (53.5 g, 197 mmol) and the reaction mixturewas stirred for 8 hr. EtOAc (600 mL) was added to the reaction mixture and the organic layerwas washed three times with water, dried, filtered, and concentrated. The crude compound wasthen purified by flash chromatography ( ethylacetatelhexanes 1 :9 ~ 3 :7) to provide sulfonate. |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h; | Step A: 4-Formyl-2-methoxyphenyl trifluoromethanesulfonate Step A: 4-Formyl-2-methoxyphenyl trifluoromethanesulfonate: To a solution of vanillin (20 g, 131 mmol) in DMF (200 mL) at room temperature was added potassium carbonate (36.30 g, 263mmol) and 4-nitrophenyl trifluoromethanesulfonate (53.5 g, 197 mmol) and the reaction mixture was stilTed for 8 hr. EtOAc (600 mL) was added to the reaction mixture and the organic layer was washed three times with water, dried, filtered, and concentrated. The crude compound was then purified by flash chromatography (ethylacetate/hexanes 1:9 -> 3:7) to provide the title compound. | |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h; | 12.A Step A: 4-Formyl-2-methoxyphenyl trifluoromethanesulfonate: To a solution of yanillin (20.0 g, 131 mmol) in DMF (200 mL) at room temperature was added potassium carbonate (36 g, 263 mmol) and 4-nitrophenyl trifluoromethanesulfonate (54.0 g, 197 mmol) and the reaction mixturewas stirred for 8 h. EtOAc (600 mL) was added to the reaction mixture and the organie layer was washed three times with water, dried, filtered, and concentrated. The crude compound was then purified by flash chromatography (ethylacetatelhexanes 1:9 -* 3:7) to proyide 4-formyl-2- methoxyphenyl trifluoromethanesulfonate._Lc/MS (IE, miz) 284.98 [M + 1]+; | |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h; | A Step A: 4-formyl-2-methoxyphenyl trifluoromethanesulfonate: General procedure: To a solution of vanillin (20 g, 131 mmol) in DMF(200 mL) at room temperature was added potassium carbonate (36.30 g, 263 mmol) and 4-nitrophenyl trifluoromethanesulfonate(53.5 g, 197 mmol) and the reaction mixture was stirred for 8 hr. EtOAc (600 mL) was added to thereaction mixture and the organic layer was washed three times with water, dried, filtered, and concentrated. Thecrude compound was then purified by flash chromatography (ethylacetate/hexanes 1:9 → 3:7) to provide sulfona | |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h; | Step A: 4-formyl-2-methoxyphenyl trifluoromethanesulfonate: Potassium carbonate (36 g, 263 mmol) and 4-nitrophenyl trifluoromethanesulfonate (54.0 g, 197 mmol) was added to a solution of vanillin (20.0 g, 131 mmol) in DMF (200 mL) at rt and the reaction mixture was stirred for 8 h. EtOAc (600 mL) was added to the reaction mixture and the organic layer washed three times with water, dried, filtered, and concentrated. The crude compound was then purified by flash chromatography (10 -30% ethylacetate/hexanes) to provide 4-formyl-2-methoxyphenyl trifluoromethanesulfonate. LC/MS: [(M+l)]+ = 285 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In water; N,N-dimethyl-formamide | 12.b (b) (b) Methyl 5-methyl-2-trifluoromethanesulphonyloxybenzoate: 13.48 g (81.13 mmol) of methyl 2-hydroxy-5-methylbenzoate obtained in Example 12(a), 22.42 g (162.3 mmol) of potassium carbonate and 135 ml of DMF are introduced into a 500 ml round-bottomed flask under a stream of nitrogen. The mixture is cooled to 0° C. and 22.0 g of 4-nitrotrifluoromethanesulphonyloxybenzene dissolved in 80 ml of DMF are added dropwise. The reaction medium is stirred for two hours 30 minutes at room temperature and then water and ethyl ether are added. The product is extracted with ethyl ether and the organic phase is washed with water to neutral pH, dried over magnesium sulphate and filtered. After evaporating the solvents, 23.89 g (99%) of the expected compound are collected in the form of a colourless liquid. 1 H NMR (CDCl3) δ 2.43 (s, 3H), 3.96 (s, 3H), 7.18 (d, 1H, J=8.4 Hz), 7.41 (dd, 1H, J=8.4/2.3 Hz), 7.89 (d, 1H, J=2.1 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With tetrabutylammomium bromide; caesium carbonate; triphenylphosphine In N,N-dimethyl acetamide at 90℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With palladium diacetate; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate monohydrate; palladium diacetate / toluene 2: palladium on activated charcoal; hydrogen / ethanol 3: hydrogenchloride; sodium nitrite / water / Cooling with ice 4: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; triethylamine / 1,4-dioxane / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0) In toluene at 80℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.2% | Stage #1: tetrakis(dimethylamido)diborane With potassium acetate; 2,2-Dimethyl-1,3-propanediol In toluene Stage #2: para-nitrophenyl triflate In toluene at 80℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: tetrakis(dimethylamido)diborane; 2,2-Dimethyl-1,3-propanediol With potassium acetate In toluene at 80℃; Stage #2: para-nitrophenyl triflate With tetrakis(triphenylphosphine) palladium(0) In toluene at 80℃; for 22h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); at 110℃; for 8h; | Step B: 4-Formyl-2-methoxybenzonitrile: A mixture of the sulfonate (37.0 g, 130 mmol), zinc cyanide (61.1 g, 521 mmol) and tetrakis triphenyiphosphine palladium (0) (22.57 g, 19.53 mmol) in DMF (300 mL) were stirred at 110 C for 8 hr. EtOAc was added to the reaction mixture and the organic layer was washed two times with water, dried, filtered and concentrated. The crude product was then purified by column chromatography (silica gel, ethylacetate/hexanes 3:7) whichafforded the title compound: LC/MS: (IE, m/z) [M + 1] = 162.34. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 48% 2: 2% 3: 3% | With bis-triphenylphosphine-palladium(II) chloride; lithium chloride In N,N-dimethyl-formamide at 100 - 105℃; for 2.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With copper(l) iodide; sulfur; sodium t-butanolate at 60 - 80℃; for 2h; | Unsymmetrical Diaryl Sulfides from Arylboronic Acid and Phenolic Esters; General Procedure General procedure: A one-necked flask was charged with CuI (30 mg, 0.15 mmol), NaOt-Bu (376 mg, 4.0 mmol), S8 (47 mg, 1.5 mmol), phenolic ester (1 mmol), arylboronic acid (1.1 mmol), and PEG200 (2 mL). The mixture was magnetically stirred and heated at 60-80 °C for the appropriate reaction time (Table 2). After completion of the reaction, the reaction mixture was cooled to r.t. H2O (4 mL) was added and the product was extracted with EtOAc (3 × 4 mL) and dried (anhyd Na2SO4). Evaporation of the solvent and purification by column chromatography on silicagel (n-hexane/EtOAc) gave the desired unsymmetrical diaryl sulfides in 74-95% yields. |
88 %Chromat. | With sulfur; nickel(II) ferrite; sodium t-butanolate at 90℃; for 4h; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With potassium fluoride; copper diacetate; potassium carbonate; sulfur at 80℃; for 0.1h; | C-S Bond Formation by the Reaction of Triphenyltin Chloride with Phenolic Esters; General Procedure General procedure: A one-necked flask was charged with Cu(OAc)2 (30 mg, 0.15 mmol), K2CO3 (414 mg, 3.0 mmol), S8 (48 mg, 1.5 mmol), KF (180 mg, 3 mmol), phenolic ester (1 mmol), triphenyltin chloride (0.35 mmol), and PEG200 (1.5 mL). The mixture was magnetically stirred and heatedat 80 °C for the appropriate reaction time (Table 4). After completion of the reaction, the reaction mixture was cooled to r.t. H2O (4 mL) was added and the product was extracted with EtOAc (3 × 4 mL) and dried (anhyd Na2SO4). Evaporation of the solvent and purification by column chromatography on silica gel (n-hexane/EtOAc) gave the desired phenyl aryl sulfides in 79-94% yields. |
93 %Chromat. | With sulfur; potassium fluoride; nickel(II) ferrite; potassium carbonate at 85℃; for 0.3h; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In dimethyl sulfoxide at 90℃; for 4h; Schlenk technique; Inert atmosphere; |
Tags: 17763-80-3 synthesis path| 17763-80-3 SDS| 17763-80-3 COA| 17763-80-3 purity| 17763-80-3 application| 17763-80-3 NMR| 17763-80-3 COA| 17763-80-3 structure
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H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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