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CAS No. : | 355408-55-8 | MDL No. : | MFCD05155252 |
Formula : | C9H13BO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OQCFQKMFRXSPPP-UHFFFAOYSA-N |
M.W : | 196.07 | Pubchem ID : | 11805632 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.56 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 55.65 |
TPSA : | 46.7 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.66 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.58 |
Log Po/w (WLOGP) : | 1.52 |
Log Po/w (MLOGP) : | 0.92 |
Log Po/w (SILICOS-IT) : | 2.27 |
Consensus Log Po/w : | 1.46 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.9 |
Solubility : | 0.247 mg/ml ; 0.00126 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.21 |
Solubility : | 0.121 mg/ml ; 0.000618 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.79 |
Solubility : | 0.322 mg/ml ; 0.00164 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.16 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 | UN#: | |
Hazard Statements: | H302-H312-H332 | Packing Group: | |
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 potassium phosphate In N,N-dimethyl-formamide at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Stage #1: thiophene With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 1h; Stage #2: With boric acid tributyl ester In tetrahydrofuran; hexane at -90℃; for 1h; Stage #3: 2,2-Dimethyl-1,3-propanediol In tetrahydrofuran; hexane at 20℃; for 0.25h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 110℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 110℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 110℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 110℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 110℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In benzene | ||
Esterification; | ||
In benzene Reflux; |
Inert atmosphere; | ||
In toluene at 20℃; for 12h; | ||
In diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In toluene for 20h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Stage #1: carbon dioxide; 5,5-dimethyl-2-(thiophen-2-yl)-1,3,2-dioxaborinane With potassium <i>tert</i>-butylate; silver(I) acetate; triphenylphosphine In tetrahydrofuran at 70℃; for 16h; Inert atmosphere; Autoclave; Stage #2: With hydrogenchloride In tetrahydrofuran; water Inert atmosphere; | |
83% | With potassium <i>tert</i>-butylate; copper(l) chloride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 70℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65.2% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 15h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With 1,1'-bis-(diphenylphosphino)ferrocene; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); triethylamine In toluene at 23 - 100℃; Inert atmosphere; | |
92% | With 1,1'-bis-(diphenylphosphino)ferrocene; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); triethylamine; zinc In toluene at 100℃; for 1h; Inert atmosphere; | |
66% | With 1,1'-bis(diphenylphosphino)ferrocene; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); triethylamine In toluene at 100℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); 1,3-bis-(diphenylphosphino)propane; triethylamine In toluene at 23 - 100℃; Inert atmosphere; | |
95% | With 1,1'-bis-(diphenylphosphino)ferrocene; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); triethylamine; zinc In toluene at 100℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 76% 2: 20% | With 1,1'-bis-(diphenylphosphino)ferrocene; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); triethylamine; zinc In toluene at 100℃; for 7h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | Stage #1: 2-bromothiophene With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; diisopropopylaminoborane; triethylamine; triphenylphosphine In tetrahydrofuran at 65℃; for 12h; Inert atmosphere; Stage #2: 2,2-Dimethyl-1,3-propanediol In tetrahydrofuran at 0 - 25℃; for 0.25h; Inert atmosphere; Further stages; | 4.3. General procedure for the synthesis of an aryl boronic ester from the reaction of aryl iodides or bromides with BH2N(iPr)2 in the presence of a palladium catalyst General procedure: Triphenylphosphine (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 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 neopentyl glycol (6 mL, 1 M solution in THF, 6 mmol) was slowly added through the condenser. After warming to 25 °C and stirring for 15 min. 1 M HCl (6 mL) was added and the mixture was filtered through a pad of Celite. The mixture was then extracted with diethyl ether (3×10 mL), combining all the organic fractions together. The organic fractions were then washed with a brine solution (2×10 mL), dried with magnesium sulfate and filtered. The solvent was removed under reduced pressure yielding 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborinane as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8 %Chromat. | With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; tricyclohexylphosphine In tetrahydrofuran at 25℃; for 47h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; tricyclohexylphosphine In tetrahydrofuran at 25℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; tricyclohexylphosphine In tetrahydrofuran at 25℃; for 12h; Inert atmosphere; | |
67% | With potassium phosphate; trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); tricyclohexylphosphine In tetrahydrofuran at 25℃; for 48h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); triphenylphosphine; zinc at 100℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; tricyclohexylphosphine In tetrahydrofuran at 25℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; tricyclohexylphosphine In tetrahydrofuran at 25℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate; lithium tert-butoxide In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With bis(1,5-cyclooctadiene)nickel(0); potassium <i>tert</i>-butylate; N,N'-dimesityl-4,5-dihydro-1H-imidazolium tetrafluoroborate In tetrahydrofuran; toluene; butan-1-ol at 20℃; for 24h; Inert atmosphere; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With dodecacarbonyl-triangulo-triruthenium; 3-ethylpentan-3-ol for 24h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88 % ee | Stage #1: 5,5-dimethyl-2-(thiophen-2-yl)-1,3,2-dioxaborinane With 1-((1S,2S)-2-hydroxyindan-1-yl)-3-pentamethylphenylimidazolinium hexafluorophosphate; sodium methylate; copper(l) chloride In tetrahydrofuran at 20℃; for 0.0833333h; Stage #2: (E)-diethyl (3-phenylbut-2-en-1-yl) phosphate In tetrahydrofuran at 30℃; for 40h; Overall yield = 85 %; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With bis-triphenylphosphine-palladium(II) chloride In 1,2-dimethoxyethane at 60℃; for 12h; | Reaction of triarylantimony diacetates with tetra(alkoxo)diborons General procedure: A solution of triarylantimony diacetate (1: 0.5mmol), tetra(alkoxo)diboron (11: 1.5mmol), and dichlorobis(triphenylphosphine)palladium (II) (0.005mmol) in DME (5mL) was stirred at 60 °C for 12h under air atmosphere. After dilution with CH2Cl2 (30mL) and water (20mL), the reaction mixture was separated and the aqueous layer was extracted with CH2Cl2 (30mL×2). The combined organic layer was washed with brine, dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatograph on silica gel to give arylboronates (12, 14-23). The products were confirmed by comparison of NMR data and MS spectra with that in the literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With water; copper diacetate; lithium tert-butoxide In 1,2-dimethoxyethane at 20℃; Inert atmosphere; | Di-tert-butyl 1-Arylhydrazine-1,2-dicarboxylates 3; General Procedure General procedure: To a 10-mL, two-necked flask (flask A) were added Cu(OAc)2 (4.5 mg, 0.025 mmol) and LiOt-Bu (60.0 mg, 0.75 mmol), and the atmosphere inside the flask was replaced with N2 by flushing (3 ×). To the flask, DME (0.5 mL) and H2O (4.5 μL, 0.025 mmol) were added and the mixture was stirred for over 15 min. To another 10-mL two-necked flask (flask B), arylboronic ester 1 (0.25 mmol) and di-tert-butyl azodicarboxylate (2, 115.1 mg, 0.5 mmol) were added, and after flushing the atmosphere in the flask with N2 (3 ×), DME (0.5 mL) was added. The solution in flask B was added to flask A via syringe within 1 min. Flask B was rinsed with DME (0.2 mL) and the solution was added to the flask A. After stirring for 13.5-16 h at r.t., the reaction was diluted with EtOAc (4 mL) and H2O (2-3 mL) and quenched with 1 M citric acid to neutralize the system. The organic layer was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel) to provide the hydrazine. Di-tert-butyl 1-(Thiophen-2-yl)hydrazine-1,2-dicarboxylate (3l) [6a]. Pale red solid; yield: 44.7 mg (57%); Rf = 0.31 (hexane-EtOAc, 5:1). 1H NMR (400 MHz, CDCl3): δ = 1.50, 1.52 (overlapped s, 18 H), 6.69-6.92 (m, 4 H). 13C NMR (100 MHz, CDCl3): δ = 28.2, 28.2, 82.0, 83.2, 114.7, 119.4, 124.8, 144.6, 152.6, 154.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dodecacarbonyl-triangulo-triruthenium; (E)-benzalacetone In toluene at 125℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With styrene; carbonylchlorohydridobis(triisopropylphosphine)ruthenium(II); cesium fluoride In toluene at 80℃; for 1h; Glovebox; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With 4'-phenyl-2,2':6',2-terpyridine; potassium methanolate; cobalt(II) chloride In N,N-dimethyl-formamide at 80℃; for 16h; Sealed tube; Inert atmosphere; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Stage #1: epoxybutene; 5,5-dimethyl-2-(thiophen-2-yl)-1,3,2-dioxaborinane With N,N,N,N,-tetramethylethylenediamine; copper(l) chloride; lithium tert-butoxide In N,N-dimethyl-formamide at 60℃; for 10h; Inert atmosphere; Stage #2: ethyl acetate In N,N-dimethyl-formamide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; silver(l) oxide In tert-Amyl alcohol at 120℃; for 16h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With potassium phosphate; palladium diacetate; ruphos In toluene at 60℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With water; caesium carbonate; nickel(II) acetylacetonate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In toluene at 130℃; for 16h; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With P(t-Bu)3 Palladacycle Gen. 3; potassium trimethylsilonate In tetrahydrofuran at 23℃; for 0.0833333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | Stage #1: di-<i>tert</i>-butyl dicarbonate; 5,5-dimethyl-2-(thiophen-2-yl)-1,3,2-dioxaborinane With 4,4'-dimethyl-2,2'-bipyridines; lithium methanolate; copper(l) chloride In N,N-dimethyl acetamide at 30℃; for 6h; Inert atmosphere; Schlenk technique; Stage #2: methyl iodide In N,N-dimethyl acetamide at 30℃; for 2h; Schlenk technique; | Methyl (Het)arylcarboxylates 3a-y, 5a-e; General Procedure General procedure: A 15 mL Schlenk tube equipped with a stirrer bar was chargedwith CuCl (10 mol%), L7 (13 mol%), LiOMe (2.5 equiv), and theappropriate boronic ester 1 or 4 (0.375 mmol). The vessel wasthen evacuated and filled with Ar (three cycles). DMA (0.5 mL)and (Boc)2O (0.25 mmol) were added sequentially under Ar, andthe mixture was stirred at 30 for 6 h. MeI (5 equiv) was thenadded in air, and the mixture was stirred at 30 for additional2 h. The mixture was finally diluted with EtOAc and washedwith sat. aq NaCl (20 mL). The aqueous phase was furtherextracted with EtOAc (3 × 20 mL), and the combined organicphases were dried (Na2SO4) and concentrated. The residue waspurified by column chromatography [silica gel EtOAc-hexane(1:100 to 1:50)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With bis(1,5-cyclooctadiene)nickel (0); C15H24N2*H(1+)*BF4(1-); sodium t-butanolate In 1,4-dioxane at 110℃; for 20h; Inert atmosphere; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With C62H76N4O2Pd2S2 In toluene at 120℃; for 18h; Inert atmosphere; Sealed tube; |
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