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CAS No. : | 29540-83-8 | MDL No. : | MFCD00192507 |
Formula : | C8H7F3O3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XXSBXVHIYGQWDV-UHFFFAOYSA-N |
M.W : | 240.20 | Pubchem ID : | 572481 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 47.06 |
TPSA : | 51.75 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.61 cm/s |
Log Po/w (iLOGP) : | 1.83 |
Log Po/w (XLOGP3) : | 3.04 |
Log Po/w (WLOGP) : | 4.56 |
Log Po/w (MLOGP) : | 2.25 |
Log Po/w (SILICOS-IT) : | 1.74 |
Consensus Log Po/w : | 2.69 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.34 |
Solubility : | 0.109 mg/ml ; 0.000455 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.79 |
Solubility : | 0.0387 mg/ml ; 0.000161 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.34 |
Solubility : | 0.109 mg/ml ; 0.000454 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.24 |
Signal Word: | Danger | Class: | 8,6.1 |
Precautionary Statements: | P261-P280-P301+P310-P305+P351+P338-P310 | UN#: | 2922 |
Hazard Statements: | H301-H311-H314-H331-H351 | Packing Group: | Ⅱ |
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 |
---|---|---|
With pyridine; In dichloromethane; at 0 - 25℃; for 12h;Inert atmosphere; | General procedure: After phenols and pyridine were dissolved in dry DCM, triflic anhydridewas added slowly by syringe over 5 min at 0 C. Then the reaction mixture was allowed to bewarmed up to 25 C and further stirred at 25 C for 12 h. After the reaction mixture was quenche dwith water, the aqueous layer was extracted with CH2Cl2 and the combined organic layer was dried over Na2SO4 and then filtrated. The products were purified by regular flash chromatography (petroleumether/EtOAc mixtures) [10]. | |
With pyridine; In dichloromethane; at 0 - 25℃; for 12h;Inert atmosphere; | General procedure: Under N2 atmosphere, phenols and pyridine were dissolved in dry CH2Cl2, then, triflic anhydride was added slowly by syringe over 5 min at 0C. Then the reaction mixture was allowed to be warmed up to 25C and further stirred at 25C for 12 h. After the reaction mixture was quenched with water, the aqueous layer was extracted with CH2Cl2 and the combined organic layer was dried over Na2SO4 and then filtrated. The products were purified by regular flash chromatography (petroleum ether/EtOAc mixtures).1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Pd(dba)2; In diethyl ether; toluene; | EXAMPLE 2 Representative example of Method B: 1-(4-methylphenyl)piperidine STR3 This example is representative of procedure "B". Into a screw-capped test tube were weighed 29 mg (0.052 mmol) Pd(dba)2, 55 mg (0.10 mmol) DPPF, and 144 mg (1.5 mmol) NaO-t-Bu. The solid materials were suspended in 12 ml of toluene. 4-Methylphenyltriflate (240 mg, 1.0 mmol) was dissolved in 1 ml of toluene and added to the test tube. The test tube was sealed with a cap containing a PTFE septum and removed from the dry box. Piperidine (148 μl, 1.5 mmol) was added to the test tube by syringe. The reaction mixture was heated at 100 C. for 5 hours. TLC of the reaction mixture indicated complete consumption of the starting triflate. The reaction mixture was cooled to room temperature, and the mixture was absorbed onto silica gel. Chromatography on a silica gel column using 50:1 hexanes:diethyl ether afforded 1-(4-methylphenyl)piperidine as a clear oil. (135 mg, 77% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Pd(dba)2; In diethyl ether; toluene; | EXAMPLE 11 N-Isobutyl-4-methylaniline STR12 Into a screw-capped test tube were weighed 10 mg (0.017 mmol) of Pd(dba)2, 21 mg (0.034 mmol) of BINAP, and 50 mg (0.65 mmol) of NaO-t-Bu. The solid materials were suspended in 8 ml of toluene. 4-Methylphenyltriflate (80 mg, 0.33 mmol) was dissolved in 1 ml of toluene and added to the test tube. The test tube was sealed with a cap containing a PTFE septum and removed from the dry box. Isobutylamine (50.0 μl, 0.50 mmol) was added to the test tube by syringe. The reaction mixture was heated at 100 C. for 3 hours. A TLC of the reaction mixture indicated complete consumption of the starting triflate. The reaction mixture was cooled to room temperature, and the mixture was absorbed onto silica gel. Chromatography on a silica gel column using 30:1 hexanes:diethyl ether afforded N-Isobutyl-4-methylaniline as a pale yellow oil (35 mg, 65% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | General procedure: Triphenylphosphene (0.131 g, 0.5 mmol, 20 mol %), p-iodoanisol (0.585 g, 2.5 mmol), and triethylamine (1.78 mL, 12.5 mmol) were added to a 50 mL round-bottomed flask equipped with a sidearm, condenser, and stir bar. This solution was then degassed by alternating vacuum and argon three times. Palladium dichloride (0.023 g, 0.13 mmol, 5 mol %) was then added under positive argon pressure. After stirring at room temperature for 15 min, diisopropylaminoborane (5 mL, 1 M solution in THF, 5 mmol) was added and the reaction mixture was degassed again by alternating vacuum and argon three times. The reaction solution was then heated to reflux. After 12 h of reflux the reaction was cooled to 0 C and 6 mL of methanol was added through the condenser slowly (Caution: exothermic reaction with evolution of hydrogen). After 15 min of stirring all the solvent was removed under reduced pressure to yield a black solid. This solid was dissolved with sodium hydroxide (3 M, 8 mL) and subsequently washed with hexanes (3×10 mL). The aqueous layer was then cooled to 0 C (ice bath) and acidified to pH ≤1 with concentrated HCl, with the boronic acid usually precipitating out as a white solid. The aqueous fraction was then extracted with diethyl ether (3×10 mL). The organic fractions were combined, dried with magnesium sulfate and filtered. The solvent was then removed under reduced pressure yielding a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | General procedure: To a stirred solution of DIAD (1.2 mmol) in DMF (2 mL) at 0 C,NaH (0.05 g, 1.2 mmol) was added in portions over 20 min.Then, the aryl O-triflate (1.0 mmol), LiI (134 mg, 1mmol), andCu2O (15 mg, 0.1 mmol) were added to the reaction mixture,which was stirred at 80 C for 8 h under N2. The reaction wascooled and quenched by adding CH2Cl2 (2 mL) and sat. aq NH4Cl(3 mL). The mixture was stirred for an additional 30 min, andtwo layers were separated. The aqueous layer was extractedwith CH2Cl2 (3 × 2 mL), the combined organic layers were driedover MgSO4, filtered, and concentrated in vacuo. The residuewas purified by chromatography (silica gel; hexane-EtOAc, 3:1)to give the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With tetrabutylammonium acetate; palladium diacetate; at 35℃; for 4h;Green chemistry; | General procedure: A mixture of Pd(OAc)2 (5 mg, 0.02 mmol), aryl source (1 mmol), sulfonamide source (1.0 mmol), Cu(OAc)2 (9 mg, 0.05 mmol; in the presence of sulfonyl azides), and TBAA (2.0 mmol) in PEG-400 (3 g) was stirred for the appropriate time at 35-50C under air. The crude reaction mixture was diluted with EtOAc (5 mL) and a saturated NH4Cl solution (5 mL). The mixture was stirred for an additional 30 min and the layers were separated. The aqueous layer was extracted with EtOAc (6 mL × 3). The combined organic layers were dried over MgSO4, filtered, and concentrated under vacuo. The residue was purified by column chromatography (silica gel, hexane:EtOAc 1:3) to give the desired product. Spectral data for all compounds except 6c, 6f, and 6n have been reported in previous reports.[19,30,31] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With bis(acetato)bis(triphenylphosphine)palladium(0); In dimethyl sulfoxide; at 60℃; under 760.051 Torr; for 12h; | Operation: 1.2mmol of the aryl sulfonate, 1 mmol of aryl boronic acid, 2ml 0.05mmol solvent containing the catalyst is added in a round bottom flask and carbon monoxide in 1atm stirred 12 hours at 60 degrees Celsius. Completion of the reaction to room temperature, filtered off solid, extracted three times with 2mL of ether was added 1mL water, and the combined extracts were spin dry solvent, column separation derived products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel (0); sodium carbonate; In 1,4-dioxane; at 80℃; for 20h;Inert atmosphere; | General procedure: Under a N2 atmosphere, 0.2 mmol aryl triflate 1a, 0.2 mmol Ph2P(O)H 2a,10 mol% Ni(COD)2, 10 mol% dppf,1.0 equiv Na2CO3 and 2 mL dioxane were charged into a 10 mL schlenck tube. The mixturewas stirred at 80 C for 20 h. After removal of the volatile, the residues were passed through a short silica chromatography (particlesize 37-54 mm, petroleum ether/ethyl acetate as eluent) toafford analytically pure organophosphorus compounds 3. Purification by chromatography (petroleum ether/EtOAc = 1:1) afforded 3d (50.8 mg, 87%) as a white solid. Rf = 0.28 (petroleum ether/EtOAc = 1:1); 1H NMR (400 MHz CDCl3): δ 7.66 (dd, J = 7.6 Hz, J = 11.6 Hz, 4H), 7.58-7.52 (m, 4H), 7.47-7.43 (m, 4H), 7.28-7.27 (m, 2H), 2.40 (s, 3H). 13C NMR (100 MHz CDCl3): δ 142.47 (d, JC-P = 2.8 Hz), 132.83 (d, JC-P = 103.5 Hz), 132.14 (d, JC-P = 10.1 Hz), 132.08 (d, JC-P = 9.9 Hz), 131.84 (d, JC-P = 2.7 Hz), 129.27 (d, JC-P = 12.5 Hz), 129.16 (d, JC-P = 106.0 Hz), 128.46 (d, JC-P = 12.1 Hz), 21.63 (d, JC-P = 1.0 Hz). 31P NMR (162 MHz CDCl3): δ 29.23 ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at 0℃; for 24h; | General procedure: A mixture of phenol (0.45 g, 5 mmol), trifluoromethanesulfonyl chloride (0.8 mL, 7.5 mmol) and Et3N (1.4 mL, 10 mmol) in THF (30 mL) was stirred at 0 C for 24 h. The solvent was evaporated and to the resulting residue were added H2O (20 mL) and EtOAc (20 mL). The organic phase was decanted and dried (anhyd Na2SO4). Evaporation of the solvent and purification by column chromatography on silica gel (hexane/EtOAc, 4:1) gave the pure triflate in 85% yield (191 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With copper(l) iodide; sulfur; sodium t-butanolate; In N,N-dimethyl-formamide; at 120℃; for 6h;Inert atmosphere; | General procedure: A one-necked flask was charged with CuI (10 mg, 0.05 mmol), NaOt-Bu (376 mg, 4.0 mmol), S8 (16 mg, 0.5 mmol), phenolic ester (1 mmol), anhyd DMF (2 mL) under an inert atmosphere. The mixture was magnetically stirred and heated at 120 C for the appropriate reaction time (Table 6). After completion of the reaction, the 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 symmetrical diaryl sulfides in 75-93% yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With copper(l) iodide; sulfur; sodium t-butanolate; at 60 - 80℃; for 13h; | 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With copper(l) iodide; sulfur; sodium t-butanolate; at 60 - 80℃; for 16h; | 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium fluoride; copper diacetate; potassium carbonate; sulfur; at 80℃; for 5h; | 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tris-(dibenzylideneacetone)dipalladium(0); N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; trifluoroacetic acid; CyJohnPhos; at 130℃; for 24h;Inert atmosphere; Schlenk technique; | Under an argon atmosphere,To the dried 25 ml Schlenk tube containing a magnetic stirrer, 27.8 mg of tris(dibenzylidenefluoreneacetone)dipalladium was added in an orderly manner.2-(dicyclohexylphosphino)biphenyl 21mg,N-(octaaminoquinoline)but-3-enamide 63.6 mg,1,8-bisdimethylaminonaphthalene 192mg,)110 mg of <strong>[29540-83-8]p-methylphenyl trifluoromethanesulfonate</strong>,Anhydrous N,N-dimethylpropenyl urea 5.5 mL and trifluoroacetic acid 74 uL were dried.Cover the tube tightly,And stir the mixture vigorously in a preheated 130 C oil bathMix for 24 hours and the reaction is over.Purified by silica gel column,Obtaining pure carboxylic acid derivative 87mg,The yield was 95%.N-(octaaminoquinoline)but-3-enamide:Aryl triflate:Tris(dibenzylidenefluoreneacetone) dipalladium:2-(Dicyclohexylphosphino)biphenyl:1,8-bisdimethylaminonaphthalene:Trifluoroacetic acid = 1:1.5:0.1:0.2:3:3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium phosphate; In toluene; at 100℃; for 20h;Inert atmosphere; Schlenk technique; | General procedure: Under N2 atmosphere, 0.2 mmol phenyl triflate 1a, 0.3 mmol Ph2P(O)H 2a, 2.5 equiv K3PO4 and 2 mL toluene were charged into a 10 mL schlenk tube. The mixture was stirred at 100C for 20 h. After removal of the volatile, the residues were passed through a short silica chromatography (particle size 37~54 mm, petroleum ether/ethyl acetate as eluent) to afford analytically pure organophosphorus compounds 3. |
73% | With potassium phosphate; In toluene; at 100℃; for 20h;Inert atmosphere; Sealed tube; | This embodiment provides a method for preparing 4-methylphenyl diphenylphosphinate, as follows: Under a nitrogen atmosphere, Add 0.30 mmol of diphenylphosphine oxide to the reactor, 0.20mmol <strong>[29540-83-8]4-methylphenyl trifluoromethanesulfonate</strong>, 0.50mmol potassium phosphate, 1.5mL toluene solvent, sealed tube, heated to 100 C, continued stirring for 20h, stopped the reaction, cooled to room temperature, washed with water to remove excess alkali and generated salt in the reaction, extracted the aqueous phase with dichloromethane to obtain organic Phase, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, the crude product was separated by column chromatography to obtain the target product, the isolated yield was 73%. |
Tags: 29540-83-8 synthesis path| 29540-83-8 SDS| 29540-83-8 COA| 29540-83-8 purity| 29540-83-8 application| 29540-83-8 NMR| 29540-83-8 COA| 29540-83-8 structure
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P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
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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