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[ CAS No. 19013-30-0 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 19013-30-0
Chemical Structure| 19013-30-0
Structure of 19013-30-0 *Storage: {[proInfo.prStorage]}

Quality Control of [ 19013-30-0 ]

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Alternatived Products of [ 19013-30-0 ]
Alternatived Products of [ 19013-30-0 ]

Product Details of [ 19013-30-0 ]

CAS No. :19013-30-0MDL No. :MFCD01231360
Formula : C8H10O4S Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :202.23Pubchem ID :-
Synonyms :

Computed Properties of [ 19013-30-0 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 19013-30-0 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 19013-30-0 ]

  • Downstream synthetic route of [ 19013-30-0 ]

[ 19013-30-0 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 19013-30-0 ]
  • [ 62-53-3 ]
  • [ 1208-86-2 ]
YieldReaction ConditionsOperation 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;
  • 2
  • [ 905966-40-7 ]
  • [ 19013-30-0 ]
  • [ 729-17-9 ]
YieldReaction ConditionsOperation 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.
  • 3
  • [ 19013-30-0 ]
  • [ 668987-38-0 ]
  • [ 213596-33-9 ]
YieldReaction ConditionsOperation 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.
  • 4
  • [ 19013-30-0 ]
  • [ 213596-33-9 ]
  • [ 2132-80-1 ]
YieldReaction ConditionsOperation 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.
  • 5
  • potassiumhexacyanoferrate(II) trihydrate [ No CAS ]
  • [ 19013-30-0 ]
  • [ 874-90-8 ]
YieldReaction ConditionsOperation 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.
  • 6
  • [ 1268340-93-7 ]
  • [ 19013-30-0 ]
  • [ 46441-11-6 ]
YieldReaction ConditionsOperation in experiment
80% With potassium phosphate; palladium diacetate; XPhos In water; <i>tert</i>-butyl alcohol at 110℃; for 18h; Inert atmosphere; Sealed tube;
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