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CAS No. : | 214360-66-4 | MDL No. : | MFCD05663843 |
Formula : | C16H25BO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SAWJXFQIAPLBEA-UHFFFAOYSA-N |
M.W : | 260.18 | Pubchem ID : | 2757248 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.62 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 82.19 |
TPSA : | 18.46 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -4.64 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 4.58 |
Log Po/w (WLOGP) : | 3.28 |
Log Po/w (MLOGP) : | 2.79 |
Log Po/w (SILICOS-IT) : | 3.13 |
Consensus Log Po/w : | 2.75 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.44 |
Solubility : | 0.00944 mg/ml ; 0.0000363 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.69 |
Solubility : | 0.00529 mg/ml ; 0.0000203 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.21 |
Solubility : | 0.0016 mg/ml ; 0.00000617 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.07 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-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 |
---|---|---|
80% | With 1H-imidazole; iron(III) chloride; In water; acetonitrile; at 20℃; for 0.5h;Inert atmosphere; | General procedure: To a solution of aryl boronic acid (1 mmol) in MeCN (4 mL) was added, sequentially, asolution of FeCl3 (8 mg, 0.05 mmol, 5 mol%) in H2O (1 mL), imidazole (204 mg, 3 mmol)and pinacol (118 mg, 1 mmol). The resulting cloudy orange mixture was stirred at roomtemperature for 30 min. The reaction was then diluted with H2O (5 mL) and extracted withEt2O (3 x 8 mL). The combined organic extracts were dried (Na2SO4) and concentrated invacuo. The resulting oil was then purified by a filtration through a silica gel plug (eluting withEt2O), affording the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium phosphate tribasic heptahydrate; chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl tert-butyl ether; XPhos; In ethanol; at 20℃; for 0.5h;Catalytic behavior; | Method (1): Synthesis from 4-tert-butylchlorobenzene as a raw material: K3P04 · 7H20 (3.0 g, 8.85 mmol) and bis-pinacol borate (749 mg, 2.95 mmol) were sequentially added to the reaction flask.The catalyst-chloro (2-dicyclohexyl phosphino-2 ', 4', 6'-tri - triisopropyl-1,1'-biphenyl) (1,1'-biphenyl -2-amino-2'_ -yl)palladium(II) (12 mg, 0.015 mmol) and ligand 2-dicyclohexylphosphine-2',4',6/-triisopropylbiphenyl (4 mg, 0.008 mmol), followed by EtOH (6 mL) The mixture was stirred, and p-tert-butylchlorobenzene (0.5 mL, 2.95 mmol) was added and the mixture was reacted at room temperature for 0.5 h. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (2 mL) After washing with ethyl acetate (6 mL) in three portions, the filtrate was combined, and the solvent was evaporated to dryness, and the solvent was separated by silica gel (200 to 300 mesh). The eluent was petroleum ether and ethyl acetate. 10~80:1), obtained as a white solid, identified by NMR spectrum as 4-tert-butylphenylboronic acid pinacol ester, yield 98% |
72% | With (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride; dichlorobis(trimethylphosphine)nickel; In tetrahydrofuran; at 100℃; for 12h;Inert atmosphere; Sealed tube; | Under an argon atmosphere,4.2 mg (0.015 mmol) of dichlorobis (trimethylphosphine) nickel,83.8 mg (0.5 mmol) of <strong>[3972-56-3]4-tert-butyl-1-chlorobenzene</strong>,152 mg (1.0 mmol) of cesium fluoride,140 mg (0.55 mmol) of 4,4,5,5,4 ', 4', 5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolanyl)180 mg (1.05 mmol) of trimethyl (2,2,2-trifluoroethoxy) silane and 0.5 mL of tetrahydrofuran were added and sealed,And the mixture was stirred at 100 C. for 12 hours.After the reaction vessel was cooled to room temperature, 1 mL of a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted three times with 8 mL of ethyl acetate, and the obtained organic phases were combined.The solvent was distilled off under reduced pressure, and the residue was purified using silica gel column chromatography (hexane: chloroform: ethyl acetate = 16: 4: 0 to 16: 4: 1)2- (4-tert-butylphenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane93 mg (white solid, yield 72%) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dimethyl sulfoxide; at 20℃; for 0.5h; | General procedure: General procedure: The synthetic procedure for pentafluorophenyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonate (a) is presented as an example (Scheme 1). 2,2'-Bis(1,3,2-benzodioxaborole) (cat2B2, 262 mg, 1.10 mmol), PdCl2(dppf) (25 mg, 0.030 mmol), AcOK (294 mg, 3.0 mmol), pentafluorophenyl 4-bromobenzenesulfonate (403 mg, 1.0 mmol), and EtOH (6.0 mL) were charged in a reaction vessel under an Ar atmosphere. The resulting mixture was stirred for 2 h at 80 C. After cooling to room temperature, pinacol (260 mg, 2.20 mmol) was added to the mixture. The mixture was further stirred for 30 min at room temperature. H2O and n-hexane were added to the mixture and the product was extracted into the organic layer. After drying the organic layer with anhydrous MgSO4, solids were removed by filtration. The filtrate was concentrated. The product was obtained as a white solid by Kugelrohr distillation. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In water; toluene; at 95℃; for 18h;Inert atmosphere; Schlenk technique; | In a clean Schlenk tube, l,3-dibromo-5-iodobenzene (1.81 g, 5 mmol) was added to 2- (4-tert-butylphenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (1 g, 3.84 mmol), K3P04 (1.63 g, 7.68 mmol) and PdCl2(dppf) (0.155 g, 0.19 mmol) along with 10 ml toluene and 1 ml water. The Schlenk tube was degassed by three freeze-pump-thaw cycles and then purged with nitrogen and the mixture was stirred at 95C for 18 hours. The reaction mixture, cooled to room temperature, was then quenched with water (25 mL) and extracted with ethyl acetate (30 mL x 3). The combined organic layers were washed with a saturated aqueous solution of NaHCC>3 (50 mL) and brine (50 mL), dried over anhydrous Na2S04 and evaporated under reduced pressure. The residue was purified using column chromatography using pure hexane Yield = 0.6 g, (43%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium phosphate tribasic heptahydrate; chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl tert-butyl ether; XPhos; In ethanol; at 20℃; for 0.5h; | General procedure: Method (1): Synthesis from 4-tert-butylchlorobenzene as a raw material: K3P04 · 7H20 (3.0 g, 8.85 mmol) and bis-pinacol borate (749 mg, 2.95 mmol) were sequentially added to the reaction flask.The catalyst-chloro (2-dicyclohexyl phosphino-2 ', 4', 6'-tri - triisopropyl-1,1'-biphenyl) (1,1'-biphenyl -2-amino-2'_ -yl)palladium(II) (12 mg, 0.015 mmol) and ligand 2-dicyclohexylphosphine-2',4',6/-triisopropylbiphenyl (4 mg, 0.008 mmol), followed by EtOH (6 mL) The mixture was stirred, and p-tert-butylchlorobenzene (0.5 mL, 2.95 mmol) was added and the mixture was reacted at room temperature for 0.5 h. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (2 mL) After washing with ethyl acetate (6 mL) in three portions, the filtrate was combined, and the solvent was evaporated to dryness, and the solvent was separated by silica gel (200 to 300 mesh). The eluent was petroleum ether and ethyl acetate. 10~80:1), obtained as a white solid, identified by NMR spectrum as 4-tert-butylphenylboronic acid pinacol ester, yield 98% |
73% | With meso-tetra(p-tolyl)porphinato-palladium(II); potassium acetate; In 1,4-dioxane; at 110℃; for 10h; | General procedure: Aryl/heteroaryl bromide 1 (1 mmol), B2pin2(2), B2npg2(4) orBpin (6, 1.2 mmol), and dioxane (5 mL) are taken into a 25 mLround-bottomed flask. KOAc (2 mmol) was added and stirredthe resultant mixture at room temperature for 5 min, PdII-TpTP(0.15 mol%) was added, and the contents were refluxed on preheatedoil bath at 110 C under constant stirring in open-air.The reaction progress was ensured by TLC. After completion ofthe reaction, the mixture was cooled, dilute with water (20 mL)and extracted with tertbutylmethyl ether (3 × 10 mL). The combinedn-hexane layers were concentrated, and the crudeproduct obtained was purified by column chromatography (CC)on silica gel using a mixture of ethyl acetate and hexane (1:30)as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.058 g | With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In tetrahydrofuran; water; for 24h;Inert atmosphere; Reflux; | A mixture of 4-tert-butylphenyl boronic ester (26 mg, 0.10 mmol), compund 16 (0.35 g, 0.47mmol), NaHCO3 (0.35 g), THF (25 mL) and H2O (4 mL) was degassed, Pd(PPh3)4 (10mg, 0.009 mmol) was added under a nitrogen atmosphere. The mixture was heated at reflux and stirred under nitrogen for 24 h. Water and CH2Cl2(200 mL) were added, the organic layer was separated and dried over Na2SO4. After removal of the solvent, the residue was chromatographically purified on silica gel eluting with petroleum ether to afford 21(0.058 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | General procedure: Aryl amine (10 mmol) was dissolved in a mixture of 5 mL of distilled water and 3.4 mL of 50% hydrofluoroboric acid. After cooling the reaction mixture to 0 C using ice bath and the sodium nitrite (0.69 g in 2 mL distilled water), was added dropwise in 5 min interval of time. The resulting mixture was stirred for 1 h and the precipitate was collected by filtration and redissolved in minimum amount of acetone. Diethylether was added until precipitation of aryl diazonium tetrafluoroborate, which is filtered, washed several times with diethyl ether and dried under vacuum. Typical reaction procedure: General procedure: Diazonium tetrafluoroborate salts (0.5 mmol) and B2pin2 (1.5 mmol) were transferred into an oven-dried tube under air. Then acetone/H2O (2/1, 4 mL) were added into the tube via syringe. The sealed tube was keep at 20 C and stirred for 1-2 h. After the reaction was complete, dichloromethane was added to extract the product and the combined organic solution was dried by Na2SO4. The pure product was isolated after column chromatography on silica gel (petroleum ether/ethyl acetate). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With tributylphosphine; Ni(1,5-cyclooctadiene)2; lithium carbonate; In 1,4-dioxane; toluene; at 160℃; for 36h;Inert atmosphere; Sealed tube; Glovebox; | In a nitrogen-filled glovebox, a 10-mL oven-dried sealed tube containing a stirring bar was charged with amide 6 (0.20 mmol, 1.0 equiv), yellow Ni(COD)2 (5.5 mg, 10 mol%) and lithium carbonate(22.2 mg, 0.30 mmol, 1.5 equiv). Subsequently, freshly distilled toluene (1.0 mL) was added, and then bis(pinacolato)diboron 9 (76.2 mg, 0.30 mmol, 1.5 equiv) and tri-n-butylphosphine ligand (20 muL, 40mol%) were added respectively via microsyringe. The tube with the mixture was sealed and removed from the glovebox. After stirring at 160 C for 36 h, the mixture was then allowed to cool to room temperature, diluted with EtOAc (5 mL) and filtered through a celite plug, eluting with additionalEtOAc (10 mL). The filtrate was concentrated and purified by column chromatography on silica gel toyield the title product 10. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With sodium t-butanolate; In tetrahydrofuran; toluene; at 120℃; for 6h;Sealed tube; | General procedure: 1-methoxy-4-iodobenzene (47 mg, 0.20 mmol) was reacted with 1,1-diboxoethane (114 mg, 0.40 mmol) and sodium tert-butoxide base (38 mg, 0.40 mmol) was placed in a 4 mL vial.Toluene / tetrahydrofuran (2.0 mL, 1: 1 mixed solution) was then added.This vial is sealed with PTFE / silicone coated cap 6 hours at 120 oC The reaction proceeded.The reaction solution was filtered through celite with dichloromethane, and the organic material was concentrated under reduced pressure. As a resultThe formation of the boronated compound 2- (4-Methoxyphenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was confirmed by nuclear magnetic resonance imaging apparatus and gas chromatography apparatus. (Yield of 35 mg, 75%); |
Tags: 214360-66-4 synthesis path| 214360-66-4 SDS| 214360-66-4 COA| 214360-66-4 purity| 214360-66-4 application| 214360-66-4 NMR| 214360-66-4 COA| 214360-66-4 structure
[ 1220219-36-2 ]
(1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropyl)methanol
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[ 627526-56-1 ]
2-(3-Cyclopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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[ 1080632-76-3 ]
2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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[ 207611-87-8 ]
4,4'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl
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[ 651030-55-6 ]
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzeneethanol
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[ 1220219-36-2 ]
(1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropyl)methanol
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[ 627526-56-1 ]
2-(3-Cyclopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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[ 1080632-76-3 ]
2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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[ 207611-87-8 ]
4,4'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl
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4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzeneethanol
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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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