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CAS No. : | 19013-30-0 | MDL No. : | MFCD01231360 |
Formula : | C8H10O4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 202.23 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
99% | With triethylamine In ethyl acetate at 0 - 20℃; for 0.166667h; Green chemistry; | 3. General Procedure for the Synthesis of Aryl Mesylates (Table 4) General procedure: To a solution of hydroxyarene (25.0 mmol) in ethyl acetate (75 mL) at 0 °C was added triethylamine (5.06 g, 50.0 mmol) followed by MsCl (3.72 g, 32.5 mmol). After addition of MsCl, the ice-water bath was removed and the resulting thick slurry was vigorously stirred for 10 min. To the slurry was then added water (50 mL). The two-phase mixture was separated. The organic layer was washed with water (25 mL) and dried over anhydrous MgSO4. Removal of solvent under reduced pressure gave the corresponding pure aryl mesylate. |
95% | With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; | |
90% | With triethylamine In dichloromethane at 0 - 20℃; | General procedure for synthesis of aryl mesylates General procedure: To a solution of phenol substrate (1.0 eq, 10.0 mmol) and Et3N (1.5 eq, 15.0 mmol) in CH2Cl2 (0.5 g/mL) was added dropwise the solution of MsCl (1.2 eq, 12.0 mmol) in CH2Cl2 at 0 oC. The mixture was allowed to warm to RT and stirred for 4 h-12 h to detect for the reaction completion. The reaction solution was added to H2O (20 ml). The layers were separated and the aqueous layer was extracted with CH2Cl2 (10 mL× 2). The combined organic layers were washed with brine (20 mL), and dried over Na2SO4. After the solvent was evaporated, the product was purified by column chromatography over silica gel. |
87.8% | With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; | |
77% | With pyridine | |
With triethylamine In benzene at 10℃; various concentrations; | ||
With pyridine In benzene at 50℃; | ||
With triethylamine further amines, effect of solvents; activation energy, preexponential terms; activation entropy; | ||
With sodium hydroxide | ||
With pyridine | ||
With pyridine | ||
With triethylamine In dichloromethane at 0℃; for 0.75h; | ||
With sodium hydride In tetrahydrofuran at 20℃; | ||
With pyridine In dichloromethane cooling; | ||
With triethylamine In dichloromethane | ||
With triethylamine In dichloromethane | ||
With triethylamine In dichloromethane | ||
With pyridine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere; | ||
With pyridine In dichloromethane Inert atmosphere; | ||
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 20% 2: 12% | With sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide at 140℃; for 20h; Title compound not separated from byproducts; | |
1: 12% 2: 20% | With sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide at 140℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); tricyclohexylphosphine tetrafluoroborate; potassium carbonate In water; toluene at 20℃; for 24h; Inert atmosphere; | |
89% | With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride; tricyclohexylphosphine In 1,4-dioxane at 80℃; for 14h; | |
89% | With potassium phosphate; C58H72N2O4P2Pd2 In <i>tert</i>-butyl alcohol at 110℃; for 8h; Inert atmosphere; |
89% | With potassium phosphate; 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; palladium diacetate In <i>tert</i>-butyl alcohol at 110℃; for 8h; Inert atmosphere; | |
80% | With potassium phosphate; 1-methyl-2-(2-(dicyclohexylphosphino)phenyl)-1H-benzoimidazole; palladium diacetate In <i>tert</i>-butyl alcohol at 20 - 120℃; for 24h; | |
75% | With potassium phosphate; C17H36ClN6NiP2(1+)*Cl(1-) In toluene at 135℃; for 16h; Inert atmosphere; | |
54% | With potassium phosphate; ferrocenylmethylphosphine In tetrahydrofuran at 20℃; for 48h; | |
21% | With potassium phosphate; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride In toluene at 110℃; for 24h; | |
39 % Chromat. | With potassium phosphate; zinc In tetrahydrofuran at 67℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54 % Chromat. | With zinc In tetrahydrofuran for 10h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 18 % Chromat. 2: 82 % Chromat. | With triphenylphosphine; zinc In N,N-dimethyl-formamide at 80℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With methanol; potassium iodide; zinc In N,N-dimethyl-formamide at 50℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With CsCO3 In dimethyl sulfoxide at 80℃; for 30h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | Stage #1: n-butyllithium; 4,5-dimethyl-2-(4-methylphenyl)-1,3,2-dioxaborolane With bis(triphenylphosphine)nickel(II) chloride In tetrahydrofuran at 20℃; for 0.25h; Stage #2: p-methoxyphenyl mesylate In tetrahydrofuran at 60℃; for 41h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 75% 2: 14% | With triethylamine; acetone In 2,2,2-trifluoroethanol for 60h; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With triethylamine; acetone In 2,2,2-trifluoroethanol for 60h; Irradiation; | |
68% | With potassium phosphate; 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; palladium diacetate In <i>tert</i>-butyl alcohol at 20 - 110℃; for 18h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With triethylamine; acetone In 2,2,2-trifluoroethanol for 60h; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); caesium carbonate; XPhos In 1,4-dioxane at 160℃; for 0.333333h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; palladium diacetate; potassium carbonate; phenylboronic acid In <i>tert</i>-butyl alcohol at 110℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium phosphate;bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; In tetrahydrofuran; at 20 - 25℃; for 8 - 12h;Product distribution / selectivity; | In a glove box with N2 atmosphere, a Schlenk tube was charged with aryl halide, tosylate or mesylate (1.0 equiv), aryl neopentylglycolboronate (1.5 equiv), potassium phosphate (0.9 mmol, 3.0 equiv), Ni(COD)2 (0.018 mmol, 0.06 equiv), tricyclohexylphosphine (0.11 mmol, 0.18 equiv), and a Teflon coated stirbar. Dry THF (2 ml) was added and reaction was left stirring for 8 h at rt. The reaction mixture was diluted with DCM (10 mL) and filtered. The filtrated solid was washed with DCM (100 mL) and the organic solvent concentrated. The coupling products were precipitated in MeOH and the white crystals were filtrated and washed with cold MeOH. |
97% | With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine; In tetrahydrofuran; at 23℃; for 1h;Inert atmosphere; Glovebox; Sealed tube;Catalytic behavior; | General procedure: 3.1 General Procedure 1 for the Cross-Coupling of 4-Methoxyphenyl Halides and Mesylates with Aryl Neopentylglycolboronates Catalyzed by Ni-Precatalysts and Mixed-Ligand Systems in Dry THF at 23 C In an oven dried test tube charged with a Teflon coated stirring bar, aryl halide or aryl mesylate (0.3 mmol), <strong>[905966-40-7]methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate</strong> (78.13 mg, 0.315 mmol), K3PO4(H2O)3.2 ((191.00 ± 1.00 mg, 0.9 mmol) and Ni-catalyst were added (in the case of NiIICl(1-naphthyl)(PCy3)2 (11.18 ± 0.0510 mg, 0.015 mmol, 5% catalyst loading) and NiIICl(1-naphthyl)(PPh3)2) (11.73 ± 0.0510 mg, 0.015 mmol, 5% catalyst loading). The test tube was brought into a nitrogen filled glove box (moisture level < 2 ppm) through three degassing cycles and PCy3 (8.4 mg, 0.03mmol, 10% loading) ligand was added. In the case of Ni(COD)2 (4.12 ± 0.0510 mg, 0.015 mmol, 5% catalyst loading), it was also added inside the glove box. Dry THF (1 mL) was added inside the glove box and the test tube was sealed by a rubber septum and left stirring at 23C.. A sample was taken by syringe and transferred outside the glove box. The sample was diluted by distilled THF (0.2 mL) and filtered through a short column of aluminum oxide. The filtrate was concentrated and the GC analysis was carried out. The reaction mixture was diluted with dichloromethane (2 mL), filtered through a layer of aluminum oxide and washed with dichloromethane (1 mL) three times. The filtrate was collected and concentrated under vacuum. The crude product was purified by column chromatography on silica gel with EtOAc/hexane mixture as eluent. The reductive elimination side-product was also isolated and characterized. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | With triethylamine;bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; In toluene; at 100℃; for 18h;Inert atmosphere;Product distribution / selectivity; | A round-bottom flask charged with the aryl halide (5.0 mmol, 1.0 equiv), Ni (For exact amount of catalyst and co-ligand see Table 8; 10% loading was used for Ni catalysts not specified in Table 8). (NiCl2(L)x , Ni(COD)2) or Pd (No co-ligand was used for Pd catalyst) catalysts (PdCl2(dppf)) (0.5 mmol, 0.1 to 0.02 equiv), ligand (L: dppp, dppe, dppf, PPh3, Et3N, bpy, PCy3) (0.5 mmol, 0.1 equiv), and a Teflon coated stir bar was evacuated three times for 10 min under high vacuum and backfilled with N2. Toluene (5 mL) and base (Et3N or (i-Pr)2EtN (15.0 mmol, 3.0 equiv) were added to the reaction mixture at rt. Freshly prepared neopentylglycolborane (10.0 mmol, 2.0 equiv in 5 ml toluene) was added to the red colored suspension via syringe at 23 0C. The reaction mixture was heated to 100 0C and the conversion was followed by GC. After 2 h-12 h (reaction time depends on the type of the aryl halide; iodo derivatives were found to react faster, in 2-4 h , while bromo derivatives in 8-12h), the reaction mixture was quenched via slow addition of saturated aqueous ammonium chloride (10 mL). The quenched reaction mixture was three times washed with saturated aqueous ammonium chloride and extracted with ethyl acetate (50 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated. The crude product was purified by silica gel chromatography or recrystallization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With potassium phosphate;bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; In tetrahydrofuran; at 20 - 25℃; for 8 - 12h;Product distribution / selectivity; | In a glove box with N2 atmosphere, a Schlenk tube was charged with aryl halide, tosylate or mesylate (1.0 equiv), aryl neopentylglycolboronate (1.5 equiv), potassium phosphate (0.9 mmol, 3.0 equiv), Ni(COD)2 (0.018 mmol, 0.06 equiv), tricyclohexylphosphine (0.11 mmol, 0.18 equiv), and a Teflon coated stirbar. Dry THF (2 ml) was added and reaction was left stirring for 8 h at rt. The reaction mixture was diluted with DCM (10 mL) and filtered. The filtrated solid was washed with DCM (100 mL) and the organic solvent concentrated. The coupling products were precipitated in MeOH and the white crystals were filtrated and washed with cold MeOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; tetrabutyl ammonium fluoride; palladium diacetate; acetic acid In <i>tert</i>-butyl alcohol at 90℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; potassium phosphate; palladium diacetate; triethylamine In <i>tert</i>-butyl alcohol at 20 - 110℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With bis(1,5-cyclooctadiene)nickel(0); potassium phosphate; tricyclohexylphosphine tetrafluoroborate In water; <i>tert</i>-butyl alcohol at 110℃; for 4h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; palladium diacetate; potassium carbonate In water; <i>tert</i>-butyl alcohol at 80℃; for 18h; Inert atmosphere; | |
85% | With di-tert-butyl{2′-isopropoxy-[1,1′-binaphthalen]-2-yl}phosphane; palladium diacetate; potassium carbonate; phenylboronic acid In water; <i>tert</i>-butyl alcohol at 120℃; for 24h; Inert atmosphere; Schlenk technique; | general procedures for the cyanation of aryl chlorides and mesylates General procedure: An oven-dried Schlenk tube was evacuated and backfilled with nitrogen. The Schlenk tube was charged with Pd(OAc)2 (4.5 mg, 0.02 mmol ), L1 (36.5 mg, 0.08 mmol), PhB(OH)2 (6.1 mg, 0.05 mmol), and t-BuOH (2 mL), and the mixture was stirred for half hour at 50 °C. After cooling to r.t., aryl chloride or mesylates (1.00 mmol), K4[Fe(CN)6]·3H2O (211.2 mg, 0.50 mmol), K2CO3 (138.2 mg, 1.00 mmol), and H2O (2 mL) were added. The septum was replaced with an inside reflux condenser, and then the Schlenk tube was placed in an oil bath preheated to 100 °C (120 °C for aryl mesylates) with stirring for 6 h (24 h for aryl mesylates). Then the reaction mixture was allowed to cool to r.t., extracted with CH2Cl2, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With palladium diacetate; cesium fluoride; XPhos In toluene; <i>tert</i>-butyl alcohol at 110℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With palladium diacetate; caesium carbonate; cesium pivalate; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 120℃; | |
46% | Stage #1: benz<b>oxazole; p-methoxyphenyl mesylate With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; palladium diacetate; potassium carbonate; triethylamine Inert atmosphere; Stage #2: In N,N-dimethyl-formamide; <i>tert</i>-butyl alcohol at 110℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium phosphate; palladium diacetate; XPhos In water; <i>tert</i>-butyl alcohol at 110℃; for 18h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium acetate In <i>tert</i>-butyl alcohol at 90℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With potassium phosphate; 1,1'-bis(diisopropylphosphino)ferrocene; (2'-amino-[1,1'-biphenyl]-2-yl)palladium(II)chloride dimer In water; <i>tert</i>-butyl alcohol at 110℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With potassium phosphate; palladium diacetate; ruphos In water; <i>tert</i>-butyl alcohol at 110℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; tricyclohexylphosphine In tetrahydrofuran at 25℃; for 8h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; tricyclohexylphosphine In tetrahydrofuran at 25℃; for 12h; Inert atmosphere; | |
81% | With potassium phosphate; trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); tricyclohexylphosphine In tetrahydrofuran at 25℃; for 13h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; tricyclohexylphosphine In tetrahydrofuran at 25℃; for 12h; Inert atmosphere; | |
96% | With potassium phosphate; trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); tricyclohexylphosphine In tetrahydrofuran at 25℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate In toluene; <i>tert</i>-butyl alcohol at 120℃; for 17h; Inert atmosphere; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With 1,1'-bis-(diphenylphosphino)ferrocene; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; N-ethyl-N,N-diisopropylamine; zinc In N,N-dimethyl-formamide at 100℃; for 36h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With 1,1'-bis-(diphenylphosphino)ferrocene; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; N-ethyl-N,N-diisopropylamine; zinc In N,N-dimethyl-formamide at 140℃; for 36h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With sodium t-butanolate In acetonitrile at 80℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With potassium phosphate; chloro(1-naphthyl)bis(triphenylphosphine)nickel(II); tricyclohexylphosphine In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; |