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CAS No. : | 356570-53-1 | MDL No. : | MFCD12405520 |
Formula : | C14H21BO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BOEXYCYPLLWKMJ-UHFFFAOYSA-N |
M.W : | 232.13 | Pubchem ID : | 15906197 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | 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 |
---|---|---|
94% | With sodium triethylborohydride In neat (no solvent) at 110℃; for 48h; Schlenk technique; Inert atmosphere; chemoselective reaction; | |
82% | With Pt(IPr)(divinyltetramethyldisiloxane) at 120℃; for 20h; Inert atmosphere; Sealed tube; | |
82% | With C23H38N2OPtSi2 at 120℃; for 20h; |
67% | With tert-butyl peroxide; K2CO3 In benzene under air, (t-BuO)2 2.0 equiv., K2CO3 2.0 equiv., Fe2O3 0.2 equiv.; 80 °C, 5 d; | |
58% | With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)diiridium(I) dichloride In neat (no solvent) at 80°C for 16 h; | |
58% | With N-heterocyclic carbene platinum(0) complex (7-Dipp)Pt(dvtms) at 120℃; for 20h; regioselective reaction; | |
56% | With iron(III) oxide; di-tert-butyl peroxide; potassium carbonate at 80℃; | |
55% | Stage #1: bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tert-butyl methyl ether Inert atmosphere; Stage #2: para-xylene In tert-butyl methyl ether at 80℃; for 1h; Inert atmosphere; Microwave irradiation; | |
58 % Chromat. | at 80℃; for 16h; | |
56 %Chromat. | With zirconium [2,2'-bipyridine]-5,5'-dicarboxylate metal-organic frameworks loaded with iridium In neat (no solvent) at 100℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: 4-bromo-m-xylene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78 - 20℃; for 24h; | |
74% | Stage #1: 4-bromo-m-xylene With n-butyllithium In tetrahydrofuran; hexane at -78 - -10℃; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78 - 20℃; Further stages.; | |
Stage #1: 4-bromo-m-xylene With n-butyllithium In tetrahydrofuran Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
With n-butyllithium In tetrahydrofuran at -78℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate In toluene Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With triethylamine In 1,4-dioxane Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With copper(ll) bromide In methanol Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With sodium hydrogencarbonate In 1,2-dimethoxyethane; water for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With potassium carbonate In water; toluene for 48h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With pyridine-4-carbonitrile; potassium phosphate; sodium oxalate; 2,4,5-tri(9H-carbazol-9-yl)-6-(ethyl(phenyl)amino)isophthalonitrile In acetonitrile at 20℃; for 24h; Irradiation; Inert atmosphere; Sealed tube; | |
88% | With potassium acetate In 1,4-dioxane at 110℃; for 1h; | |
86% | Stage #1: 2-chloro-1,4-dimethyl-benzene; bis(pinacol)diborane With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; XPhos at 110℃; for 6h; Schlenk technique; Inert atmosphere; Stage #2: Inert atmosphere; | Palladium-Catalyzed Borylation of Aryl Chlorides in PEG-2000;General Procedure General procedure: To a dried Schlenk tube were added Pd2dba3 (4.6 mg, 0.005 mmol),XPhos (9.6 mg, 0.02 mmol), bis(pinacolato)diboron (190 mg, 0.75mmol), PEG-2000 (1.0 g), and KOAc (147 mg, 1.5 mmol). The Schlenktube was evacuated and backfilled with argon. The reaction mixturewas heated to 50 °C, followed by the addition of the aryl chloride (0.5mmol) via syringe (aryl chlorides that were solid were added withother reagents before evacuation). The reaction mixture was thenstirred at 110 °C under Ar for 6 h. After being cooled to 45 °C, the resultingmixture was extracted with cyclohexane (3 × 5 mL). The residueof the extraction was subjected to a second run of the borylationreaction by charging with the same substrates (aryl chloride, bis(pinacolato)diboron and KOAc) under the same conditions without furtheraddition of Pd2dba3 and XPhos. The combined cyclohexane layerwas concentrated under reduced pressure. The residue was purifiedby flash column chromatography on silica gel using a mixture of petroleumether and EtOAc as eluent or by recrystallization from hexaneto afford the desired aryl boronates 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72 mg | With potassium phosphate; water In 1,4-dioxane at 110℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 65 percent / K3CO3 / tetrakis(triphenylphosphine)palladium(0) / toluene; H2O / 48 h / Heating 2: N-bromosuccinimide; azobisisobutyronitrile / CCl4 / 120 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Pd(PPh3)4; NaHCO3 / 1,2-dimethoxy-ethane 2: NaN3; NH4Cl / dimethylformamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: Pd(PPh3)4; NaHCO3 / 1,2-dimethoxy-ethane 2: NaN3; NH4Cl / dimethylformamide 3: 70 percent / pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: Pd(PPh3)4; NaHCO3 / 1,2-dimethoxy-ethane 2: NaN3; NH4Cl / dimethylformamide 3: 70 percent / pyridine 4: NBS; benzoyl peroxide / benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 56 percent / NaHCO3 / Pd(Ph3P)4 / 1,2-dimethoxy-ethane; H2O / 5 h / Heating 2: 40 percent / NBS / (PhCOO)2 / CCl4 / 3 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / pyridine / CH2Cl2 / 0.25 h / 0 °C 2: 99 percent / Et3N / PdCl2(dppf) / dioxane / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Na2CO3 / Pd(PPh3)4 / toluene / Heating 2: n-BuLi / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: Na2CO3 / Pd(PPh3)4 / toluene / Heating 2: n-BuLi / tetrahydrofuran 3: NBS; BPO / CCl4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In xylene hated at 140°C for 80 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With triethylamine at 110℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With C47H55N2Ni at 100℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; | |
21% | With C2F3O2(1-)*C21H34IrN4(1+) at 180℃; for 0.5h; Microwave irradiation; Neat (no solvent); | |
6% | With (N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)CuFp at 25℃; for 24h; Inert atmosphere; Glovebox; UV-irradiation; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II) / tetrahydrofuran; 1,4-dioxane / 18 h / Reflux 2: carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II) / 48 h / 150 °C / Inert atmosphere; Glovebox; Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ca. 14 %Spectr. | With carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II) at 150℃; for 48h; Inert atmosphere; Glovebox; Schlenk technique; | |
With (η6-mesitylene)(tris-pinacolboryl)iridium; di(2-pyridyl)(3-fluorophenyl)methane In neat (no solvent) at 120℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 3 h / 90 °C / Inert atmosphere 2: sodium hydroxide / tetrahydrofuran; methanol / 1 h / 50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.3% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 90℃; for 3h; Inert atmosphere; | 14.2 2-(3-(2',5'-dimethyl[1,1’-biphenyl]-3-yl)-2,3,7,8-tetrahydrobenzofuran[5,6-b][1,4]dioxin-8-yl)acetic acid methyl ester A mixture of 2-(3-(3-bromophenyl)-2,3,7,8-tetrahydrobenzofuro[5,6-b][1,4]dioxin-8-yl)acetic acid methyl ester 4h (150 mg, 0.37 mmol), 2-(2,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 14b , (150mg, 0.37mmol), tetrakistriphenylphosphine (21 mg, 0.021 mmol) and sodium carbonate (78 mg, 0.77 mmol) were dissolved in a mixture of 5 mL of dioxane and water (v / v = 10: 1) , heated to 90 ° C, stirring reaction for 3 hours. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography using eluent system B to give the title compound 2-(3-(2',5'-dimethyl[1,1’-biphenyl]-3-yl)-2,3,7,8-tetrahydrobenzofuran[5,6-b][1,4]dioxin-8-yl)acetic acid methyl ester 14c (80 mg, yellow liquid), yield: 50.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42.1% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,2-dimethoxyethane for 3h; Reflux; Inert atmosphere; | 14.1 2-(2,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2-bromo-1,4-dimethylbenzene 14a (1.02 g, 5.50 mmol), bis(pinacolato)diboron (1.95 g, 8.30 mmol),1,1 '-bis (diphenylphosphino) ferrocene] dichloropalladium (202 mg, 0.30 mmol) and potassium acetate (1.35 g, 13.88 mmol) was dissolved in 20 mL of ethylene glycol dimethyl ether and heated to reflux for 3 hours. Filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography using eluent system B to give the title product, 2-(2,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 14b (538 mg, yellow oil), yield: 42.1%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68 % de | With potassium phosphate; chloro(1,5-cyclooctadiene)rhodium(I) dimer In methanol; tert-butyl methyl ether at 65℃; for 16h; Microwave irradiation; Inert atmosphere; Sealed tube; Overall yield = 72 %; Overall yield = 118 mg; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With N-Bromosuccinimide; dibenzoyl peroxide In acetonitrile at 100℃; for 24h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide / acetonitrile / 24 h / 100 °C / Schlenk technique; Inert atmosphere 2.1: water; tetrahydrofuran / 1 h / 50 °C 2.2: 2 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: 2,5-Dimethylaniline With hydrogen bromide; sodium nitrite In methanol at 0℃; for 0.5h; Stage #2: bis(pinacol)diborane With sodium acetate In methanol at 25℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With tetrakis(triphenylphosphine) palladium(0); potassium phosphate monohydrate; palladium diacetate; tris-(o-tolyl)phosphine In dimethyl sulfoxide at 90℃; for 24h; | 4.3 Variant B, Single-Phase Reaction Mixture: 0.6 mmol of tri-o-tolylphosphine and then 0.1 mmol of palladium(II) acetate or 0.3 mmol of tetrakis(triphenylphosphine)palladium(0) are added to a suspension of 10 mmol of a brominated complex, 12-20 mmol of boronic acid or boronic acid ester per Br function and 60-100 mmol of the base (potassium fluoride, tripotassium phosphate (anhydrous or monohydrate or trihydrate), potassium carbonate, caesium carbonate, etc.) and 100 g of glass beads (diameter 3 mm) in 100 ml-500 ml of an aprotic solvent (THF, dioxane, xylene, mesitylene, dimethylacetamide, NMP, DMSO, etc.), and the mixture is stirred with warming (80-130° C.) for 1-24 h. Alternatively, other phosphines, such as triphenylphosphine, tri-tert-butylphosphine, S-Phos, X-Phos, RuPhos, XanthPhos, etc., can be employed, where, in the case of these phosphines, the preferred phosphine:palladium ratio is 3:1 to 1.2:1. The solvent is removed in vacuo, the product is taken up in a suitable solvent (toluene, dichloromethane, ethyl acetate, etc.) and purified as described under Variant A. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With basolite C300 In neat (no solvent) at 100℃; for 24h; | 2.4. Experimental procedure General procedure: In a 25 mL round bottom flask, toluene (1 mL), Cu3(BTC)2 (30 mg),1 (127 mg, 0.5 mmol) were charged and this slurry was stirred at 100°C. The borylation of toluene was monitored by gas chromatography(GC) and the conversion of 1 was determined at different time intervals.Similar experimental procedures were performed with radicalquenchers like TEMPO and 2,6-di-t-butyl-4-methylphenol with appropriateamount mentioned in the table. The product identity was confirmedby analyzing the reaction mixture by GC-MS. Conversion of theborylation reaction and selectivity of the products were determined byAgilent GC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 66% 2: 20 %Chromat. 3: 6 %Chromat. | With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0); potassium methanolate In hexane at 25℃; for 6h; Inert atmosphere; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With Co(0) coordinated to phosphine of porous metal organic framework formed by Zr(IV)-(tris[1,1'-biphenyl]phosphine) In neat (no solvent) at 110℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; |
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