Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | ||||||
{[ item.p_purity ]} | {[ item.pr_size ]} | Inquiry |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price) ]} |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]} | {[ item.pr_usastock ]} | in stock Inquiry - | {[ item.pr_chinastock ]} | {[ item.pr_remark ]} in stock Inquiry - | Login | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
CAS No. : | 123324-71-0 | MDL No. : | MFCD01009697 |
Formula : | C10H15BO2 | Boiling Point : | - |
Linear Structure Formula : | (HO)2BC6H4C(CH3)3 | InChI Key : | MNJYZNVROSZZQC-UHFFFAOYSA-N |
M.W : | 178.04 | Pubchem ID : | 2734320 |
Synonyms : |
|
Chemical Name : | (4-(tert-Butyl)phenyl)boronic acid |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
95% | With copper(II) choride dihydrate; sodium carbonate; In methanol; at 25℃; for 0.25h;Green chemistry;Catalytic behavior; | General procedure: Arylboronic acid (0.3 mmol), CuCl2·2H2O (2.5 mg, 5 molpercent), Na2CO3 (10 molpercent),methanol (1 mL) were added to a vial. The reaction mixture was stirred at 25 °C inthe air for 5-15 min and was monitored by TLC. Then the reaction was quenched withtwo drops of H2O, diluted with 2 mL of ethyl acetate, and filtered over a pad ofMgSO4 and silica. The pad was rinsed with additional ethyl acetate, and the solutionwas concentrated in vacuum. The crude material was loaded onto a silica gel columnand purified by flash chromatography. |
91% | With oxygen; potassium carbonate; In water; at 25℃; for 2h;Green chemistry; | General procedure: A solution of nano CuO (0.010 mmol) and substituted phenylboronic acid (1 mmol) in H2O (2 mL) was stirred at 25 °C for 2 h under aerobic condition. After the reaction was over, the reaction mixture was extracted with ethyl acetate and washed with doubledistilled water in a separating funnel. The organic layer was separated and collected in a conical flask. After evaporation of the solvent in a rotary evaporator, reaction mixture was subjected to column chromatography on silica gel column (ethyl acetate/hexane, 1:10) to afford the respective product. |
90% | With Cu2(ophen)2; In N,N-dimethyl-formamide; at 20℃; for 20h; | General procedure: 4.3. Catalytic tests: general procedure I for the Cu2(ophen)2catalyzed homocoupling for Table 2 A solution of the corresponding arylboronic acids (1.0 mmol),Cu2(ophen)2 (1.3 mg, 0.5 mol percent), DMF (1.0 mL) in 5 mL round-bottomed ask was stirred under air and the reaction was moni-tored by TLC. After the substrate was consumed, the reaction con-versions were determined bygas chromatography (GC) analysis (FIDfrom AGILENT 7820) using a cross-linked (95percent)-dimethyl-(5percent)-diphenylpolysil-oxane column (HP-5, 30 m0.32 mm0.25 mm),helium, injector temperature 250 C, detector temperature 300 C,and oven temperature program 45 C (3 min)e20C/mine280 C(2 min). The resulting mixture was poured into brine (10 mL), andextracted with diethyl ether (310 mL). The organic layer waswashed with brine, dried over Mg2SO4, the residue was chromato-graphed via a short column of silica gel (petroleum ether: diethylether15:1) and evaporated under reduced pressure. The productswas determined by 1H NMR spectroscopy. All 1H NMR spectra weremeasured in CDCl3 with TMS as the internal standard. |
75% | With [Cu(trans-cyclohexane-1,2-diamine)2(H2O)2][OTf]2; In methanol; at 20℃; for 3h; | General procedure: In a 25-mL round-bottomed flask, a solution of copper(II)complex (2 mol percent) and substituted phenylboronic acid (1.5 mmol)in methanol (5 mL) was stirred at room temperature for 3e4 h. Theprogress of the reaction was monitored by TLC. After completion ofthe reaction, the solvent was removed and the product was washedwith water and extracted with ethyl acetate (3 10 mL). Thecombined organic layers were dried over Na2SO4 and the solventremoved under reduced pressure to give crude product which waspurified by column chromatography by using petroleum ether/ethyl acetate (4:1) as an eluent. |
72% | With sodium tetrachloroaurate(III) dihyrate; potassium carbonate; In ethanol; at 50℃; for 24h; | Representative experimental procedure: A mixture of AuCl (11.6 mg, 0.050 mmol), phenylboronic acid (1a, 121.9 mg, 1.00 mmol), K2CO3 (152.0 mg, 1.10 mmol) in EtOH (8.0 mL) was heated at 50 °C under open air for 24 h. The reaction mixture was filtered through a plug of Florisil.(R). washing with hexane-AcOEt (3:1). The filtrate was concentrated under reduced pressure, and the resulting residue was subjected to preparative thin-layer chromatography (hexane:AcOEt = 20:1) to afford biphenyl (2a, 58.6 mg, 76percent). |
With oxygen; caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 1h; | In a 25 mL beaker1 g of 4-tert-butylbenzeneboronic acid, 0.2 g of Cs2C03, 3 mL of DMF and (hi g catalyst (complex 1)The reaction was complete, 10 mL of CH2CI2 was extracted and washed with 20 mL of distilled water. The organic phase was dried with sewage MgS04, filtered and the solution was removed and the crude product was obtained. The reaction mixture was stirred at room temperature for 1 hour. The petroleum ether eluted the column to give 4,4-di-tert-butylbiphenyl. | |
With Cu(1+)*BF4(1-)*C10H8N6*0.5H2O; caesium carbonate; In N,N-dimethyl-formamide; | At 25 mL Weigh 1 g in the beaker 4-tert-butylbenzeneboronic acid, 0.2 g Cs2C03, 3 mL DMF and 0.1 g catalyst (Complex 1), The mixture was stirred at room temperature for 1 hour, TLC monitoring (RhoEpsilon: EpsilonAlpha = 1: 1) The reaction was complete, 10 mL of CH2CI2 after extraction of the product And then washed with 20 mL of distilled water, Organic phase with sewage MgS04 dry, Filtration, desolvation, The resulting crude product was eluted with petroleum ether Column, get 4,4-di-tert-butylbiphenyl | |
With {Cu(1-(4-(4-(1H-1,2.4-triazol-1-yl)phenoxy)phenyl)-1H-1,2.4-triazole)2(NO3)2}; oxygen; caesium carbonate; at 20℃; for 1h; | Weigh 1 g of 4-tert-butylphenylboronic acid in a 25 mL beaker, 0.2 g Cs2CO3, 3 mL DMF and 0.1 g catalyst (complex1), Stir at room temperature for 1 hour, TLC monitoring (PE:EA = 1:1) Complete reaction, 10 mL CH2Cl2The product is extracted and washed with 20 mL of distilled water. The organic phase is treated with effluent MgSO?4Drying, filtration, desolvation, and the resulting crude product was eluted through a column with petroleum ether to give 4,4'-di-tert-butylbiphenyl. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With oxygen; triethylamine;basolite C300; In dichloromethane; at 20℃; for 5h;Product distribution / selectivity; | EXAMPLES[0008] MOF-199 (Basolite C300, Aldrich) , cyclohexylamine, triethylamine, phenylbornic acid, 4-nitrophenylboronic acid, 4-cyanophenylbornic acid, 4-chlorophenylboronic acid, 4-ter- burlyphenylboronic acid, 4- (dimehtylamino) -phenylboronic acid, naphthalene-1-bonronic acid and 1, 3, 5-trimethyoxybenzene were purchased form Aldrich Chemical Co.[0009] General homo-coupling reaction procedure:[0010] Cu3(BTC)2 (Basolite C300, provided by BASF,www.mof.basf.com, Aldrich catalogue number: 688614),cyclohexylamine, triethylamine, phenylboronic acid, 4- nitrophenylboronic acid, 4-cyanophenylboronic acid, 4- chlorophenylboronic acid, 4-tert-butylphenylboronic acid, 4-(dimethylamino) -phenylboronic acid, naphthyl-1-boronic acid and 1, 3, 5-trimethoxybenzene were purchased from AldrichChemical Co. Dichloromethane was purchased from FisherScientific International Inc. All starting materials were used without further purification. All experimental operations, unless otherwise noted, were performed in air. A mixture of arylboronic acid, (3.01 mmol) , cyclohexylamine (0.248 g, 286 muL, 2.51 mmol) and triethylamine (0.253 g, 348 muL, 2.49 mmol) were premixed and dissolved in 20 mL dichloromethane in a 50 mL round-bottom flask. MOF (0.100 g, 0.165 mmol, 0.495 mmol Cu(II)) or cupric acetate monohydrate (Cu (OAc) 2'H2O, 0.100 g, 0.501 mmol) was then added to the solution. The mixture was stirred at room temperature for 5 h, followed by filtration and washing with fresh dichloromethane. The excessdichloromethane in the filtrate was subsequently removed by rotovap . 1, 3, 5-trimethoxybenzene (0.168 g, 1.00 mmol) was added to the filtrate as internal standard for 1H NMR. Chemical shifts of all products in 1H NMR agree well with literature data .[0011] Biphenyl: 47percent yield of biphenyl (based onphenylboronic acid) was afforded when MOF was used; no biphenyl product was formed in the case of cupric acetate monohydrate. GC-MS, m/z+ 154.1; 4, 4' -dinitrobiphenyl : 87percent and 18percent yields of 4, 4' -dinitrobiphenyl (based on 4- nitrophenylboronic acid) were afforded when MOF and cupric acetate monohydrate were used, respectively. GC-MS, m/z+ 244.2; Biphenyl-4, 4' -dicarbonitrile : 92percent and 19percent yields of biphenyl-4, 4' -dicarbonitrile (based on 4-cyanophenylboronic acid) were afforded in the presence of MOF and cupric acetate monohydrate, respectively. 1.34 mmol (yield: 90percent) and 1.35 mmol (yield: 92percent) biphenyl-4, 4' -dicarbonitrile were observed in the second and third cycles, respectively. GC-MS, m/z+ 204.1; 4,4'-dichlorobiphenyl: 81percent and 8percent yields of 4,4'- dichlorobiphenyl (based on 4-chlorophenylboronic acid) were afforded in the presence of MOF and cupric acetatemonohydrate, respectively. GC-MS, m/z+ 223.1; 4, 4' -di-tert- butylbiphenyl : 25percent yield of 4, 4' -di-tert-butylbiphenyl (based on 4-tert-butylphenylboronic acid) was afforded when MOF was used, but none was formed in the case of cupric acetate monohydrate. GC-MS, m/z+ 266.1; N, N, N' ,N' -tetramethyldiphenyl- 4,4'-diamine: 43percent and 5percent yields of N, N, N', N'- tetramethyldiphenyl-4, 4' -diamine (based on 4- (dimethylamino) - phenylboronic acid) for MOF and cupric acetate monohydrate, respectively. GC-MS, m/z+ 240.1; 1, 1' -binaphthyl : 90percent and 6percent yields of 1, 1' -binaphthyl (based on naphthalyl-1-boronic acid) were afforded for MOF and cupric acetate monohydrate, respectively. GC-MS, m/z+ 254.2.[0012] Powder X-ray diffraction (PXRD) data were collected using a Bruker D8-Discover Psi-2Psi diffractometer in reflectance Bragg-Brentano geometry. Cu Ka radiation (lambda = 1.5406 A; 1,600 W, 40 kV, 40 mA) was focused using a planer Gobel Mirror riding the Ka line. A 0.6 mm divergence slit was used for all measurements. Diffracted radiation was detected using a Vantec line detector (Bruker AXS) (6° 2Psi sampling width) equipped with a Ni monochrometer . All samples were ground to ensure mono dispersity in the bulk, and then mounted onto a glass slide fixed on a sample holder by dropping powders and then leveling the sample surface with a wide-blade spatula. The best counting statistics were achieved by using a 0.02° 2Psi step scan from 1 - 50° with an exposure time of 0.4 s per step. The diffraction patterns collected for Cu3(BTC)2 both before and after homo-couplings are shown in Figures 4-10. Powder patterns of Cu3 (BTC)2 after three cycles alsoillustrated in Figure 11.[0013] FT-IR spectra of benzyltricarboxylic acid (BTC) and Cu3(BTC)2 (fresh and after coupling reaction) were obtained as KBr pellets using Nicolet 400 Impact spectrometer. FT-IR of recovered liquid after coupling reaction was performed on two clear KBr crystal plates. As shown in Figure 12 and 13, the C=O stretch of carboxylates in Cu3(BTC)2 absorbs at 1653 cm-1, whereas the C=O stretch of free carboxylic acid in BTC absorbs at 1734 cm'1, which is a strong characteristic peak for presence of any non-coordinated carboxylic groups. Recov... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃; for 3.0h;Inert atmosphere; | A 25-mL round bottom flask equipped with a magnetic stirrer, a condenser and a nitrogen in/outlet adapter was charged with <strong>[74204-00-5]3-bromo-5-methylphenol</strong> (300 mg, 1.6 mmol), 4- tert-butylphenylboronic acid (428 mg, 2.1 mmol), water/dioxane (1 mL/3 ml), K2C03 (441 mg, 3.2 mmol). The resulting solution was degassed for 5 minutes, then Pd(PPh3)4 (60 mg) was added. The reaction mixture was warmed to 100 °C and stirred for 3 hours. After being allowed to cool to room temperature, the reaction mixture was diluted with EtOAc (100 mL) and washed with saturated NaHCO3, brine, dried over Na2SO4. The organic layer was concentrated uiider reduced pressure and purified on silica gel. Elution with EtOAc/hexanes solvent system |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7%Chromat.; 90%Chromat. | With Cu2(ophen)2; water; In ethanol; at 20℃;Green chemistry; | General procedure: 4.4. General procedure II for Table 3 A solution of arylboronic acids (1.0 mmol), Cu2(ophen)2 (1.3 mg,0.5 mol percent) in H2O-EtOH (1.8 mL, VH2O:VEtOHn:1) was stirred atroom temperature. After the substrate was consumed, the reactionconversions were determined by GC analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With C21H19N2(1+)*Br(1-); palladium diacetate; potassium carbonate; In toluene; at 70℃; for 3h; | General procedure: A reaction tube was charged with Pd(OAc)2 (1.34 mg, 0.006 mmol), imidazolium salt (0.0072 mmol), K2CO3 (62 mg, 0.45 mmol), and ArB(OH)2 (0.45 mmol). To the reaction tube were added toluene (2.0 mL) and aryl bromide (0.3 mmol). The mixture was stirred at 70 °C in the presence of air for 3 hours. The mixture was cooled to room temperature and directly purified through silica gel column chromatography to give the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34 mg; 81% | Into an argon filled two-neck flask fitted with reflux condenser and pressure-equalizing dropping funnel and containing CuCl (79 mg, 0.80 mmol), a solution of o-tert-butylnitrosobenzene 3a (130 mg, 0.80 mmol) in dry deaerated DMF (20 ml) was added. The mixture was stirred at 60°C (water bath) for 30 min. Then the solution of p-tert-butylphenylboronic 4b (155 mg, 0.87 mmol) acid in dry deaerated DMF (7 ml) was added and the mixture was stirred at 60°C for 16 h. The colour of the solution changed from light green to black via light yellow, green and greenish blue. Afterwards the mixture was diluted with water (100 ml) and saturated aqueous ammonia (50 ml) and extracted with diethyl ether. The extracts were dried with anhydrous sodium sulfate, evaporated and purified by column chromatography on silica gel (eluent, toluene?hexane, 1: 20). Three fractions were collected (in order of elution): 4,4'-di-tert-butylbiphenyl (34 mg), o-tert-butylnitrosobenzene (10 mg) and product 2 (183 mg, 81percent yield). For 2: white crystals, mp 86?88°C. 1H NMR (400 MHz, CDCl3) delta: 7.40 (dd, 1H, o-H, J 7.9 and 1.5 Hz), 7.28 (dd, 1H, o-H, J 7.9 and 1.5 Hz), 7.25?7.21 (m, 2H, p-H), 7.14 (ddd, 1H, o-H, J 7.9, 7.3 and 1.6 Hz), 7.01 (ddd, 1H, o-H, J 7.9, 7.3 and 1.5 Hz), 6.83?6.79 (m, 2H, p-H), 5.37 (s, 1H, 7-NH), 1.45 (s, 9H, But), 1.31 (s, 9H, But). 13C NMR (101 MHz, CDCl3) delta: 142.99 (p-C), 142.59 (o-C), 142.09 (o-C), 142.05 (p-C), 127.04 (o-C), 126.93 (o-C), 126.18 (p-C), 124.47 (o-C), 123.07 (o-C), 116.65 (p-C), 34.90 (CMe3), 34.19 (CMe3), 31.68 (CMe3), 30.70 (CMe3). ESI-HRMS, m/z: 228.2216 [M + H]+ (calc. for C20H28N, m/z: 282.2217). |
[ 560132-24-3 ]
3-tert-Butylphenylboronic acid
Similarity: 1.00
[ 197223-39-5 ]
(3,5-Di-tert-butylphenyl)boronic acid
Similarity: 0.98
[ 169126-64-1 ]
(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid
Similarity: 0.93
[ 560132-24-3 ]
3-tert-Butylphenylboronic acid
Similarity: 1.00
[ 197223-39-5 ]
(3,5-Di-tert-butylphenyl)boronic acid
Similarity: 0.98
[ 169126-64-1 ]
(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid
Similarity: 0.93