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[ CAS No. 280559-30-0 ]

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Chemical Structure| 280559-30-0
Chemical Structure| 280559-30-0
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CAS No. :280559-30-0 MDL No. :MFCD09953475
Formula : C15H23BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :246.15 g/mol Pubchem ID :-
Synonyms :

Safety of [ 280559-30-0 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P312-P322-P330-P363-P304+P340-P501 UN#:
Hazard Statements:H302-H312-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 280559-30-0 ]

  • Downstream synthetic route of [ 280559-30-0 ]

[ 280559-30-0 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 98-82-8 ]
  • [ 73183-34-3 ]
  • [ 280559-30-0 ]
YieldReaction ConditionsOperation in experiment
38% With palladium on activated charcoal at 100℃; for 16h;
38% With palladium on activated charcoal In further solvent(s) byproducts: H2; 16 h at 100°C in isopropylbenzene under N2; catalyst: 10% Pd/C (6mol%);
  • 2
  • [ 280559-30-0 ]
  • [ 1123-85-9 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran; ethanol; benzene-d6 at 20℃; for 9h;
  • 3
  • [ 25015-63-8 ]
  • [ 98-83-9 ]
  • [ 280559-30-0 ]
YieldReaction ConditionsOperation in experiment
100% With sodium triethylborohydride at 23℃; Inert atmosphere; 9 MOF-Co catalysts are also active in hydroborylation of alkenes or dehydrogenative C-H borylation of arenes to afford alkyl or arylboronates, which are versatile reagents in organic synthesis. Alkene hydroboration reactions were performed with 0.1-0.01 mol % MOF-Co in a neat, 1:1.2 equiv mixtures of alkene and pinacolborane (HBpin) at room temperature to obtain the highest yields (Table 11). At a 0.1 mol % Co loading, bpyv-MOF-Co gave complete conversion of 1-octene within 16 h at room temperature to furnish a mixture of 66% anti-Markovnikov octylboronate ester and 34% internal alkenes. However, under identical reaction conditions, mPT-MOF-Co afforded exclusively octylboronate ester in 97% yield with TON up to 10,000 (Table 11). The hydroboration of other terminal alkenes such as 1-decene, 5-methyl-1-hexene and 6-chloro-1-hexene occurred selectively in anti-Markovnikov fashion to afford corresponding alkylboronates in excellent yields with 0.1-0.01 mol % mPT-MOF-Co. mPT-MOF-Co was also active in catalytic hydroboration of internal alkenes. Importantly, mPT-MOF-Co can be recycled at least 15 times without any noticeable diminishing activity in hydroboration of 1-octene. A negligible leaching of Co (<0.01%) and Zr (<0.005%) was observed into the supernatant after run 1. No hydroboration reaction was observed after removal of mPT-MOF-Co from the reaction mixture, which rules out any role of leached cobalt species in catalyzing hydroboration. Additionally, Co-nanoparticles or homogeneous controls, Me2bpy-Co and PT-Co, are barely active in catalyzing hydroboration reactions (e.g., entry 1, Table 11). The higher activities of MOF-Co catalysts strongly support the beneficial effect of active site isolation in the MOF frameworks, which prevents any intermolecular deactivation. (0238) [table-us-00011-en] TABLE 11 MOF-Co-Catalyzed Hydroboration of Alkenesa Co-catalysts % Yield Entry Substrate Product (mol % loading) Time (TONs) 1-octene bpyv-MOF-Co (0.1) mPT-MOF-Co (0.1) mPT-MOF-Co (0.01) 16 h 16 h 3 h 66 (660) 100 (>1000) 100 (10000) CoCl2 (0.1) 20 h 0 Co(Me2bpy)Cl2 (0.1) 20 h 37 1-decene mPT-MOF-Co (0.1) 16 h 100 (>1000) mPT-MOF-Co (0.1) mPT-MOF-Co (0.01) 16 h 4 d 100 (>1000) 100 (10000) mPT-MOF-Co (0.1) 2 d 86 mPT-MOF-Co (0.1) 18 h 100 (>1000) mPT-MOF-Co (0.1) (0240) RRN 78Inspired by the high activity of mPT-MOF-Co in alkene hydroboration, the catalytic activity of MOF-Co catalysts in dehydrogenative borylation of aromatic C-H bonds were investigated. In homogeneous catalysis, although a number of nitrogen and phosphine-based iridium(I) catalysts have been reported, the bipyridyl- or phenanthryl-derived iridium catalysts are the most active and widely used in C-H borylation. Efforts in developing heterogeneous borylation catalysts has been made based on precious metals such as iridium(0) nanoparticles, insoluble iridium complex, or silica-supported rhodium and iridium catalysts. Recently, bis(imino)pyridine- and bis(phosphino)pyridine-supported cobalt catalysts have been reported for arene C-H borylation. mPT-MOF-Co was initially employed in C-H borylation reactions for optimized conditions such as temperature, activating and borylating reagents, solvents, and in neat arenes (without using a solvent) to obtain the best results. The screening experiments revealed that the highest yields were obtained when the borylation reactions were performed in neat arene at 100° C. or refluxed in n-heptane at 100° C. for solid substrates. mPT-MOF-Co catalyzed borylation of o- and m-xylene occurred selectively at the least sterically hindered C-H bonds. 1,2-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-m-xylene were obtained from o- and m-xylene in 90 and 92% yield, respectively, with 0.1 mol % mPT-MOF-Co (e.g., entries 1 and 2, Table 12). Although only phenylboronate was afforded from benzene as a monoborylated product, the borylation of toluene furnished a mixture of meta- and para-substituted products in a 60:40 ratio. Interestingly, both mPT-MOF-Co is significantly more active in C-H borylation of arenes than their homogeneous control PT-Co. 1.0 mol % of PT-Co afforded 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-m-xylene from m-xylene in only 8% conversion in four days, after which no further conversion was observed with further heating. In contrast, the conversion of m-xylene proceeded with time until completion in the presence of 0.1 mol % mPT-MOF-Co (FIG. 5). This result indicates that mPT-MOF-Ir is at least 125 times more active than the homogeneous control for the C-H borylation reaction. (0241) [table-us-00012-en]
99% With Co(0) coordinated to phosphine of porous metal organic framework formed by Zr(IV)-(tris[1,1'-biphenyl]phosphine) In tetrahydrofuran at 23℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox;
98% With C39H48FeN2Si In hexadeuterobenzene at 60℃; for 3h; Glovebox; Inert atmosphere; Schlenk technique;
96% With bis(cycloocta-1,5-diene)rhodium (I) tetrafluoroborate; 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 20 - 40℃; for 16h; Inert atmosphere;
91% With C37H40OTi In tetrahydrofuran at 100℃; for 8h; Inert atmosphere; Glovebox; Sealed tube; Schlenk technique;
89% With tris(3,4,5-trifluorophenyl)borane In chloroform at 180℃; for 1.5h; Inert atmosphere; Microwave irradiation; Sealed tube;
87% With (1,4-bis(diphenylphosphino)butane)(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; tris(pentafluorophenyl)borate In 1,1-Dichloroethylene at 70℃; for 9h;
87% With n-butyllithium; 2,6-bis-[1-(2,6-diethylphenylimino)ethyl]pyridine iron(II) chloride In hexane at 20℃; for 1h; Inert atmosphere; regioselective reaction;
83% With di-μ-chlorobis-[(η6-p-cymene)chlororuthenium(II)] In neat (no solvent) at 20℃; for 24h; regioselective reaction;
83% With iron(II) tetrafluoroborate hexahydrate; (S)-(-)-2,6-diisopropyl-N-(1-(6-(4-isopropyl-4,5-dihydrooxazol-2-yl)pyridin-2-yl)ethylidene)aniline In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; enantioselective reaction;
82% With sodium triethylborohydride In tetrahydrofuran at 60℃; for 36h; Inert atmosphere; Glovebox;
72% Stage #1: 4,4,5,5-tetramethyl-1,3,2-dioxaborolane; α-methyl-styrene With 6-di-tert-butylphosphinomethyl-2,2'-bipyridine In tetrahydrofuran for 0.0166667h; Inert atmosphere; Glovebox; Schlenk technique; Stage #2: With sodium triethylborohydride In tetrahydrofuran at 25℃; for 0.5h; Inert atmosphere; Glovebox; Schlenk technique;
72% With (2,2′:6′,2″-terpyridine)CoCH2SiMe3 In 2-methoxy-2-methylpropane at 23℃; for 18h;
65% With tropylium tetrafluoroborate In neat (no solvent) at 70℃; for 12h;
64% With lithium diisobutyl-tert-butoxyaluminum hydride In neat (no solvent) at 110℃; for 6h;
46% With tris[3,5-bis(trifluoromethyl)phenyl]borane In neat (no solvent) at 80℃; for 40h; Glovebox; Inert atmosphere; regioselective reaction;
40% With triphenylphosphine; cobalt(III) acetylacetonate; sodium tertiary butoxide In tetrahydrofuran at 20℃; for 4h; Glovebox; Inert atmosphere; regioselective reaction;
33% With 2,6-bis[1-(2,6-diisopropylphenylimino)ethyl]pyridine manganese(II) bromide; sodium tertiary butoxide In neat (no solvent) at 60℃; for 18h; Inert atmosphere;
31% With lithium aluminium hydride In neat (no solvent) at 110℃; for 3h; regioselective reaction;
6% With (S)-4-benzyl-2-(pyridin-2-yl)-4,5-dihydrooxazoline; iron(II) chloride In diethyl ether at 0℃; for 1h; Inert atmosphere; Schlenk technique;
With tris[N,N-bis(trimethylsilyl)amide]lanthanum In hexadeuterobenzene at 90℃; for 144h;
In further solvent(s) (N2); treatment of styrene deriv. with pinacol borane in dichloroethane at 70°C in presence of rhodium compd. for 9 h; GC anal.;
With B(C6F5)3; [Rh(C8H12)((C6H5)2P(CH2)4P(C6H5)2)]BF4*C4H8O In further solvent(s) (N2); treatment of styrene deriv. with pinacol borane in dichloroethane at 70°C in presence of rhodium compd. and perfluorophenylborane for 9 h; GC anal.;
With [(2,6-(2,4,6-Me3-C6H2-NdCMe)2C5H3N)Fe(N2)]22-N2) In neat (no solvent) at 25℃; Inert atmosphere;
56 %Spectr. With [CeIV63-O)43-OLi)4(trimesoato(3-))2(OH)12Li6] at 100℃; for 36h; Inert atmosphere;
With sodium triethylborohydride; cobalt(II) iodide In toluene at 25℃; for 16h; Inert atmosphere; Sealed tube;
56 %Spectr. With [CeIV63-O)43-OLi)4(trimesoato(3-))2(OH)12Li6] at 100℃; for 36h; Inert atmosphere; 24 Example 24
CeH-BTC-Catalyzed Hydroboration of Alkenes General procedure: CeOH-BTC (10 mg, 21.7 μmol Ce) was prepared as described above. Styrene, as an exemplary alkene (499 μL, 4.34 mmol), was added to a solution of CeOH-BTC and 237 pinacolborane (945 μL, 6.51 mmol). The reaction mixture was stirred under nitrogen at 80° C. for 18 h. The MOF was removed from the solution by centrifugation. The supernatant was transferred to a clean round bottom flask, and the MOF was washed with THF. The combined organic extracts were concentrated in vacuo to afford 247 4,4,5,5-tetramethyl-2-(2-phenylethyl)-1,3,2-dioxaborolane (3.43 mmol, 79% NMR yield based on 248 CH3NO2 as an internal standard). Table 25 shows the results of CeH-BTC catalyzed hydroboration of various alkenes.
68 %Spectr. With N,N,N',N'-tetramethylethylenediamine adduct of 1,1'-dilithio-ferrocene In toluene at 100℃; for 18h; Inert atmosphere; Schlenk technique; Glovebox;
With silver(I) acetate In toluene at 120℃; for 24h; Schlenk technique; Inert atmosphere;

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  • 4
  • [ 25015-63-8 ]
  • [ 98-83-9 ]
  • [ 280559-30-0 ]
  • (E)-4,4,5,5-tetramethyl-2-(2-phenylprop-1-en-1-yl)-1,3,2-dioxaborolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trans-carbonyl(chloro)bis(triphenylphosphine)rhodium(I) In [D3]acetonitrile; benzene-d6 at 80℃; for 48h;
  • 5
  • [ 73183-34-3 ]
  • [ 98-83-9 ]
  • [ 1187525-03-6 ]
  • [ 280559-30-0 ]
  • (E)-4,4,5,5-tetramethyl-2-(2-phenylprop-1-en-1-yl)-1,3,2-dioxaborolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene; acetonitrile in nitrogen-filled glove box soln. of (BO2C2(CH3)4)2 and α-Me styrene in toluene/acetonitrile added to soln. of trans-Rh(Cl)(CO)(PPh3)2 (catalyst) in same solvent; mixt. stirred, transferred in sealed ampoule and heated to 80°C; not isolated, detn. by GC-MS and NMR;
In toluene in nitrogen-filled glove box soln. of (BO2C2(CH3)4)2 and α-Me styrene in toluene added to soln. of trans-Rh(Cl)(CO)(PPh3)2 (catalyst) in same solvent; mixt. stirred, transferred in sealed ampoule and heated to 80°C; not isolated, detn. by GC-MS and NMR;
  • 6
  • [ 25015-63-8 ]
  • [ 98-83-9 ]
  • [ 129813-26-9 ]
  • [ 280559-30-0 ]
  • (E)-4,4,5,5-tetramethyl-2-(2-phenylprop-1-en-1-yl)-1,3,2-dioxaborolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
0% In tetrahydrofuran-d8 THF-d8, room temp., 2 mol% of catalyst, 72 h; detected by NMR spectra;
1: 0% 2: 0% In tetrahydrofuran-d8 THF-d8, room temp., 2 mol% of catalyst, 72 h; detected by NMR spectra;
0% In tetrahydrofuran-d8 THF-d8, room temp., 2 mol% of catalyst, 72 h; detected by NMR spectra;
0% In tetrahydrofuran-d8 THF-d8, room temp., 2 mol% of catalyst, 72 h; detected by NMR spectra;

  • 7
  • [ 98-82-8 ]
  • [ 25015-63-8 ]
  • [ 280559-30-0 ]
YieldReaction ConditionsOperation in experiment
13% With palladium on activated charcoal In further solvent(s) byproducts: H2; 16 h at 100°C in isopropylbenzene under N2; catalyst: 10% Pd/C (6mol%);
  • 8
  • [ 76-09-5 ]
  • [ 98-83-9 ]
  • [ 1085319-31-8 ]
  • [ 280559-30-0 ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: isopropenylbenzene With PyBH2I In dichloromethane at 20℃; for 2h; Stage #2: With sodium hydroxide; water In dichloromethane at 0 - 20℃; Stage #3: 2,3-dimethyl-2,3-butane diol In dichloromethane; water at 20℃; for 15h;
6% Stage #1: isopropenylbenzene With Me2S-BH2I In dichloromethane at 20℃; for 2h; Stage #2: With sodium hydroxide; water In dichloromethane at 0 - 20℃; Stage #3: 2,3-dimethyl-2,3-butane diol In dichloromethane; water at 20℃; for 15h;
  • 9
  • [ 73183-34-3 ]
  • [ 98-83-9 ]
  • [ 280559-30-0 ]
YieldReaction ConditionsOperation in experiment
99% With potassium <i>tert</i>-butylate; iron(II) chloride; <i>tert</i>-butyl alcohol In tetrahydrofuran at 65℃; for 12h; Inert atmosphere; Schlenk technique; Green chemistry;
99% Stage #1: bis(pinacol)diborane With methanol; o-phenylenebis(diphenylphosphine); copper(II) bis(trifluoromethanesulfonate); sodium t-butanolate In acetonitrile for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: isopropenylbenzene In acetonitrile at 50℃; for 3h; Inert atmosphere; Schlenk technique; regioselective reaction; 4. General Procedure for Hydroboration of Alkenes General procedure: An oven-dried vial was charged with Cu(OTf)2 (0.015 mmol), Lp7 (0.03 mmol), t-BuONa (0.03 mmol) and bis(pinacolato)diboron (0.36 mmol). After being sealed with a septum, the vial was connected to an argon-vacuum line and was evacuated and backfilled with argon (x 3). CH3CN (2 mL) and methanol (0.9 mmol) were added and the mixture was stirred for 30 min. Then, Alkene (0.3 mmol) was added and the mixture got a dark brown color and was stirred at 50 oC for 3h. After 3h, ethyl acetate and water were added and the organic layer were separated. The aqueous phase was extracted with ethyl acetate(x 3) and the combined organic layers were dried over Na2SO4 and concentrated. The crude product was purified by silica gel column chromatography.
94% Stage #1: bis(pinacol)diborane With bis(1,5-cyclooctadiene)nickel(0); tricyclohexylphosphine In toluene at 20℃; for 0.166667h; Schlenk technique; Sealed tube; Inert atmosphere; Stage #2: isopropenylbenzene With water In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere; General Procedure for Ni-Catalyzed Hydrobolation of Olefins General procedure: A 20-mL sealed Schlenk tube containing a magnetic stir bar was charged with B2pin2 (38.1 mg, 0.15 mmol), Ni(cod)2 (2.8 mg, 10.0 µmol), PCy3 (5.6 mg, 20.0 µmol) and 1.0 mL of dry toluene. The mixture was stirred at room temperature for 10 min then added olefins (0.10 mmol) and H2O (3.6 mg, 0.20 mmol). The reaction vessel was sealed then heated at 100 °C for 18 h. The resulting solution was cooled to room temperature, extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4 , filtered and concentrated under reduced pressure. The crude product was purified by recycle GPC.
93% With methanol; bis(1,5-cyclooctadiene)nickel(0); tri-tert-butyl phosphine In toluene at 75℃; for 10h;
85% Stage #1: bis(pinacol)diborane; isopropenylbenzene With potassium carbonate In methanol; toluene at 60℃; for 96h; Inert atmosphere; Stage #2: With water; ammonium chloride In methanol; toluene Inert atmosphere;
74% With methanol; potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 20℃; for 24h; regioselective reaction;
68% With sodium methylate; copper(l) chloride In methanol at 40℃; for 10h; regioselective reaction;

  • 10
  • [ 280559-30-0 ]
  • [ 37778-99-7 ]
  • (+)-(R)-2-phenylpropanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide; sodium hydroxide In diethyl ether at 0 - 23℃; Inert atmosphere; optical yield given as %ee;
With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
  • 11
  • [ 280559-30-0 ]
  • [ 17435-72-2 ]
  • [ 1392215-07-4 ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: 2-(2-phenyl-2-methylethyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane With tetramethylenebis(magnesium chloride) In tetrahydrofuran; toluene at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: ethyl 2-bromomethyl-2-propenoate In tetrahydrofuran; toluene at -40℃; Inert atmosphere;
  • 12
  • [ 98-82-8 ]
  • [ 73183-34-3 ]
  • 2,2',2''-(2-phenylpropane-1,1,3-triyl)tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) [ No CAS ]
  • 2,2'-(2-phenylpropane-1,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) [ No CAS ]
  • 2,2'-(2-phenylpropane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) [ No CAS ]
  • [ 280559-30-0 ]
YieldReaction ConditionsOperation in experiment
1: 6 %Spectr. 2: 11 %Spectr. 3: 15 %Spectr. 4: 15 %Spectr. With (CyADI)Co(O2C8H15)2; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane at 100℃; for 120h; Inert atmosphere; Glovebox;
YieldReaction ConditionsOperation in experiment
99% With potassium <i>tert</i>-butylate; iron(II) chloride In tetrahydrofuran; <i>tert</i>-butyl alcohol at 65℃; for 12h; Inert atmosphere; Schlenk technique; 15 Example 1 Preparation of 2-phenylethyl-1-boronic acid pinacol ester (Compound 1) General procedure: To the argon-protected 50 ml Schlenk bottle at room temperature, the catalyst FeCl22.6 mg (0.02 mmol,1% of the molar amount of styrene), 20 mL of anhydrous THF, 208 mg (2 mmol) of styrene,Styrene molar amount of 1.5 times the boronic acid frequency of alcohol ester 762mg (3mmol),(2 mmol) of t-butanol in 1 molar equivalent, the reaction system was a light brown yellow turbid solution and allowed to react at 65 ° C for 12 hours. After completion of the removal of the solvent by rotary evaporator, 50 mL of water was added and the mixture was extracted with ethyl acetate (4 x 20 mL). The combined organic phases were washed with saturated brine (2 x 30 mL) and dried over anhydrous Na2SO4. The target compound, the filler was silica gel, the eluent was petroleum ether: ethyl acetate (100: 1-10: 1), the separation yield was 92%.
  • 14
  • [ 25015-63-8 ]
  • [ 98-83-9 ]
  • 2,2'-(2-phenylpropane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) [ No CAS ]
  • [ 280559-30-0 ]
YieldReaction ConditionsOperation in experiment
With norbornene; cobalt(II) aceylacetonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tetrahydrofuran at 50℃; for 12h; Inert atmosphere; Sealed tube;
Historical Records

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[ 280559-30-0 ]

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