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Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
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CAS No. : | 154318-75-9 | MDL No. : | MFCD28973056 |
Formula : | C11H13F3O3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LNLGXWZOBTUQSC-UHFFFAOYSA-N |
M.W : | 282.28 | Pubchem ID : | 11011452 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.45 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 61.36 |
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) : | -4.94 cm/s |
Log Po/w (iLOGP) : | 2.41 |
Log Po/w (XLOGP3) : | 4.34 |
Log Po/w (WLOGP) : | 5.55 |
Log Po/w (MLOGP) : | 3.11 |
Log Po/w (SILICOS-IT) : | 2.5 |
Consensus Log Po/w : | 3.58 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.31 |
Solubility : | 0.0139 mg/ml ; 0.0000493 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.14 |
Solubility : | 0.00204 mg/ml ; 0.00000722 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.16 |
Solubility : | 0.0197 mg/ml ; 0.0000698 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.43 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P260-P264-P280-P301+P310+P330+P331-P303+P361+P353+P310-P304+P340+P310-P305+P351+P338+P310-P363-P405-P501 | UN#: | 1759 |
Hazard Statements: | H314 | 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 |
---|---|---|
67.3% | With triethylamine; In dichloromethane; at 0℃; | Preparation of Intermediate 4-tert-butylphenyl trifluoromethanesulfonate (1C-1); To a stirred solution of 4-tert-butylphenol (2.88g, 19.2mmol) and triethylamine (4.01 ml, 28.8mmol) in dichloromethane (101 ml_) was added a solution triflic anhydride (6.8g, 24mmol) drop wise. The mixture was continued to stir at O0C for 2 hrs. The reaction mixture was washed with water and brine and dried over sodium sulfate, filtered and concentrated to give a dark brown oil. Product was purified on silica gel eluting with heptane to give 4-tert-butylphenyl trifluoromethanesulfonate (1 C-1 ) (3.64g 67.3%) as a clear oil.1 H NMR (400 MHz, CHLOROFORM-d) d ppm 1.31 (s, 9 H) 7.17 (d, J=8.72 Hz, 2 H) 7.43 (d, J=8.72 Hz, 2 H) |
67.3% | With triethylamine; In dichloromethane; at 0℃; | To a stirred solution of 4-tert-butylphenol (2.88 g, 19.2 mmol) and triethylamine (4.01 ml, 28.8 mmol) in dichloromethane (101 mL) was added a solution triflic anhydride (6.8 g, 24 mmol) drop wise. The mixture was continued to stir at 0 C. for 2 hrs. The reaction mixture was washed with water and brine and dried over sodium sulfate, filtered and concentrated to give a dark brown oil. Product was purified on silica gel eluding with heptane to give 4-tert-butylphenyl trifluoromethanesulfonate (3.64 g 67.3%) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.31 (s, 9H) 7.17 (d, J=8.72 Hz, 2H) 7.43 (d, J=8.72 Hz, 2H) |
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 |
---|---|---|
With ammonium hydroxide; CuI; sodium carbonate; In dodecane; water; ethyl acetate; N,N-dimethyl-formamide; | Example 204 4-tert-Butyl-N-hexylaniline from 4-tert-butylphenyl Trifluoromethanesulfonate CuI (10 mg, 0.05 mmol), <strong>[19311-91-2]N,N-diethylsalicylamide</strong> (39 mg, 0.20 mmol) and Na2CO3 (127 mg, 1.2 mmol) were put into a screw-capped test tube with a Teflon-lined septum. The tube was then evacuated and backfilled with argon (3 cycles). 4-tert-Butylphenyl trifluoromethanesulfonate (282 mg, 1.0 mmol), n-hexylamine (198 muL, 1.5 mmol) and DMF (0.5 mL) were added by syringes. The reaction mixture was stirred at 90 C. for 18 h. The reaction mixture was allowed to reach room temperature. Ethyl acetate (~2 mL), water (~10 mL), ammonium hydroxide (~0.5 mL) and dodecane (227 muL) were added. The organic phase was analyzed by GC and GC-MS. A 3% calibrated GC yield was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With caesium carbonate; N-ethyl-N,N-diisopropylamine; XPhos;palladium diacetate; In toluene; at 110℃; for 20h; | To degassed toluene (11.8 mL) was added beta alanine ethyl ester hydrochloride (0.354 g, 2.3 mmol), 4-tert-butylphenyl trifluoromethanesulfonate (0.5 g, 2 mmol), X-Phos (87 mg, 0.18 mmol), palladium acetate (42 mg, 0.186 mmol), diisopropylethyl amine (0.3 ml, 2 mmol), and cesium carbonate (1.73 g, 5.31 mmol). Reaction mixture was stirred at 110° C. for 20 hours. Reaction cooled to room temperature, diluted with water and extracted with ethyl acetate. Pooled organic layers washed with brine, dried over sodium sulfate and concentrated. Residue purified on silica eluding with 1percent methanol in dichloromethane to give ethyl 3-(4-tert-butylphenylamino)propanoate (0.17 g, 40percent) as an off-white solid. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.24 (s, 12H) 2.59 (t, J=6.44 Hz, 2H) 3.42 (t, J=6.44 Hz, 2H) 4.13 (q, J=7.06 Hz, 2H) 6.57 (d, J=8.72 Hz, 2H) 7.20 (d, J=8.72 Hz, 2 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
> 95%Spectr. | With nickel(II) chloride hexahydrate; potassium bromide; at 185 - 190℃; for 20h;Inert atmosphere; | General procedure: To a 10 mL 2-necked reaction flask equipped with magnetic stirrer, reflux condenser and outlet were charged NiCl2·6H2O (47.5 mg, 0.20 mmol) and KBr (952 mg, 8.0 mmol). This system was flame-dried under vacuum and filled with nitrogen gas. After cooling to room temperature, 2.0 mmol substrate and 1.5 mL P(OEt)3 were added. Then the reaction system was stirred and heated at 185~190 oC for 20 or 36 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate, and hydrogen peroxide (30% in water) was added to destruct the Ni[P(OEt)3]4. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic phase was dried with MgSO4 and filtered. The solvent was removed under reduced pressure. The residue was passed a thin layer of silica gel (200~300 mesh) to remove nickel salts to obtain a mixture of product, unreacted substrate, diethyl ethylphosphonate and triethyl phosphate. Part of the mixture and some amount of nitrobenzene or mesitylene were weighted to a NMR tube to detect the yields by 1H NMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (R)-7-bis(m-xylyl)phosphino-7-bis(3,5-dimethylphenyl)phosphinyl-1,1'-spirobiindane; N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium(0); In 1,4-dioxane; at 50℃; for 2.5h;Inert atmosphere; Glovebox; | General procedure: A. Examples of asymmetric Heck reaction of cyclic olefinsGeneral procedureIn an argon-filled glove box, Pd(dba)2 (7.2 mg, 0.013 mmol) and (R)-Xyl-SDP(O) (10.8 mg, 5 0.015 mmol) were stirred in dry 1,4-dioxane (0.50 mL) for 10 to 20 mm in a 4-mL vial, followedby addition of n-C14H30 (25 tL, GC internal standard), aryl triflate (0.50 mmol), Nethyldiisopropylamine (170 iL, 1.0 mmol, 2 equiv) and cyclic olefin (2.0 mmol, 4 quiv). The mixture was vigorously stirred in a preheated oil bath at a set temperature until the aryl triflate was fully consumed (monitored by GC). The reaction mixture was cooled to RT and subjected to10 flash chromatography (basic alumina, Brockmann grade I, pentane/Et20) to give the purified product. Silica gel may be also used for purification. The olefinic selectivity of Heck isomers in the crude mixture was determined by GC. The ee of the purified product was determined by chiral HPLC analysis with Daicel Chiralcel columns or by chiral GC analysis. Racemic products were prepared using the racemic ligand to facilitate determination of ee. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (R)-7-bis(m-xylyl)phosphino-7-bis(3,5-dimethylphenyl)phosphinyl-1,1'-spirobiindane; N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium(0); In 1,4-dioxane; at 50℃; for 4h;Inert atmosphere; Glovebox; | General procedure: A. Examples of asymmetric Heck reaction of cyclic olefinsGeneral procedureIn an argon-filled glove box, Pd(dba)2 (7.2 mg, 0.013 mmol) and (R)-Xyl-SDP(O) (10.8 mg, 5 0.015 mmol) were stirred in dry 1,4-dioxane (0.50 mL) for 10 to 20 mm in a 4-mL vial, followedby addition of n-C14H30 (25 tL, GC internal standard), aryl triflate (0.50 mmol), Nethyldiisopropylamine (170 iL, 1.0 mmol, 2 equiv) and cyclic olefin (2.0 mmol, 4 quiv). The mixture was vigorously stirred in a preheated oil bath at a set temperature until the aryl triflate was fully consumed (monitored by GC). The reaction mixture was cooled to RT and subjected to10 flash chromatography (basic alumina, Brockmann grade I, pentane/Et20) to give the purified product. Silica gel may be also used for purification. The olefinic selectivity of Heck isomers in the crude mixture was determined by GC. The ee of the purified product was determined by chiral HPLC analysis with Daicel Chiralcel columns or by chiral GC analysis. Racemic products were prepared using the racemic ligand to facilitate determination of ee. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With (o-hydroxyphenyl)diphenylphosphine; tetraethylammonium bromide; palladium diacetate; caesium carbonate; In toluene; at 120℃; for 24h;Inert atmosphere; Glovebox; | General procedure: Conditions B: To a dried screw capped vial were added aryl bromide 1 or aryl triflate 2 (0.50 mmol), Pd(OAc)2 (11.2 mg, 0.05 mmol, 10 mol %), ligand 5 (27.8 mg, 0.10 mmol, 20 mol %), Cs2CO3 (195.5 mg, 0.60 mmol, 1.2 equiv), Et4NBr (105.1 mg, 0.5 mmol, 1.0 equiv), hexamethyldigermane (3; 120 μL, 0.60 mmol, 1.2 equiv), and toluene (2.5 mL) under argon atmosphere in a glove box. The vial was capped and heated at 120 C for 24 h with stirring. After cooling to r.t., H2O (2 mL) was added. After dilution with EtOAc, the organic layer was separated, and the aqueous layer was extracted with EtOAc (3 × 3 mL). The combined organic layers were washed with brine (3 mL) and dried (Na2SO4). After filtration and evaporation, purification of the crude product by silica gel column chromatography afforded the corresponding product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | General procedure: To a 25 mL flask, 3-sulfolene (2.2 mmol) and potassium tert-butoxide (224 mg, 2 mmol) were added freshly-distilled tetrahydrofuran (4 mL), and the reaction mixture (sulfinate suspension) was stirred for 1 h at rt. An oven-dried 35 mL glass pressure tube containing an elliptical rare-earth stir bar was purged with argon through a glass pipet for 5 min. Palladium acetate (11 mg, 0.05 mmol, 5 mol%) and dppbz (36 mg, 0.08 mmol, 8 mol%, 1,2-bis(diphenylphosphino)benzene) were added, followed by freshly-distilled tetrahydrofuran (4 mL). The pressure tube was capped with a septum that was connected to an argon line and a gas-bubbler, and the reaction mixture was stirred for 15 min at rt. Potassium bicarbonate (200 mg, 2 mmol) was added. Then, the sulfinate suspension mixture was added by means of a pipette. The reaction mixture was stirred for 5 min at rt, and an aryl sulfonate (1 mmol) was added. The pressure tube was sealed with a PTFE screw cap, and the reaction mixture was stirred for 1 h at rt. The temperature was then allowed to gradually reach 100 C over 20 min, and the reaction mixture was vigorously stirred for 14-36 h at 100 C. For work-up, the reaction mixture was cooled to rt, and a saturated solution of ammonium chloride (4 mL) was added, followed by ethyl acetate (20 mL). The reaction mixture was then extracted with ethyl acetate (4 × 10 mL). The organic phases were combined, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (ethyl acetate/hexane or diethyl ether/pentane) to give the 1,3-diene product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2′-(dicyclohexylphophanyl)-N2,N2,N6,N6-tetramethyl[1,1′-biphenyl]-2,6-diamine; palladium diacetate; lithium tert-butoxide; In tert-butyl alcohol; at 82℃; for 16h;Inert atmosphere; | General procedure: A test tube was charged with Pd(OAc)2 (0.04 equiv), a phosphine ligand (0.1 equiv), and LiOtBu (2.0-3.0 equiv). The test tube was purged with N2 then the appropriate aryl or alkenyl triflate (2.0-3.0 equiv) was added, followed by the appropriate substrate (1.0 equiv) in tert-butanol (0.1M). The tube was heated to 82C and stirred overnight or until the starting material was completely consumed as judged by 1H NMR analysis. The mixture was cooled to room temperature and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2′-(dicyclohexylphophanyl)-N2,N2,N6,N6-tetramethyl[1,1′-biphenyl]-2,6-diamine; palladium diacetate; lithium tert-butoxide; In tert-butyl alcohol; at 82℃; for 16h;Inert atmosphere; | General procedure: A test tube was charged with Pd(OAc)2 (0.04 equiv), a phosphine ligand (0.1 equiv), and LiOtBu (2.0-3.0 equiv). The test tube was purged with N2 then the appropriate aryl or alkenyl triflate (2.0-3.0 equiv) was added, followed by the appropriate substrate (1.0 equiv) in tert-butanol (0.1M). The tube was heated to 82C and stirred overnight or until the starting material was completely consumed as judged by 1H NMR analysis. The mixture was cooled to room temperature and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | 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. |
68% | With potassium phosphate; In toluene; at 100℃; for 20h;Inert atmosphere; Sealed tube; | This embodiment provides a method for preparing 4-tert-butylphenyl diphenylphosphinate, as follows: Under a nitrogen atmosphere, Add 0.30 mmol of diphenylphosphine oxide to the reactor, 0.20mmol 4-tert-butylphenyl trifluoromethanesulfonate, 0.50mmol potassium phosphate, 1.5mL of toluene solvent, after sealing the tube, heat to 100 C and continue to stir for 20h, Stop the reaction, cool to room temperature, wash with water to remove excess alkali and generated salts, extract the aqueous phase with dichloromethane to obtain the organic phase, dry over anhydrous sodium sulfate, distill off the solvent under reduced pressure, and obtain the crude product by column chromatography The target product was isolated in 68% yield. |
Tags: 154318-75-9 synthesis path| 154318-75-9 SDS| 154318-75-9 COA| 154318-75-9 purity| 154318-75-9 application| 154318-75-9 NMR| 154318-75-9 COA| 154318-75-9 structure
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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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