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[ CAS No. 1150561-77-5 ]

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Chemical Structure| 1150561-77-5
Chemical Structure| 1150561-77-5
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Product Details of [ 1150561-77-5 ]

CAS No. :1150561-77-5 MDL No. :MFCD10700159
Formula : C10H19BO4 Boiling Point : 242.7±23.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :214.07 g/mol Pubchem ID :46739293
Synonyms :

Safety of [ 1150561-77-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1150561-77-5 ]

  • Downstream synthetic route of [ 1150561-77-5 ]

[ 1150561-77-5 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 1150561-77-5 ]
  • potassium 3-trifluoroboratopropionate methyl ester [ No CAS ]
  • 2
  • [ 292638-85-8 ]
  • [ 73183-34-3 ]
  • [ 1150561-77-5 ]
YieldReaction ConditionsOperation in experiment
92% Example 15: beta-Boration of methyl acrylate to methyl-3-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan- 2-yl)-propanoate in water: In a dry two-necked round bottom flask were placed catalyst CuC03 basic (0.03 mmol, 3 mol% according to starting material) and ligand Ph3P (0.035 mmol, 3.5 mol% according to starting material) under the nitrogen. Afterwards 2.5 mL of deionized water was added and reaction mixture was vigorously (900 rpm) stirred at ambient temperature for 20 min. The boronating reagent bis(pinacolato)diboron (B2pin2; 1 .1 mmol, 280 mg, 1 .1 equiv.) was added in one portion and such reaction mixture was stirred at ambient temperature for 30 min. Starting material methyl acrylate (1 .0 mmol, 86 mg) was slowly added into the reaction system and such reaction mixture was intensively stirred at 27 C for 12 hours. The reaction mixture was diluted with brine (5 mL) and extracted with EtOAc (2 x 40 mL). Combined organic layers were again washed with brine (30 mL), dried over Na2S04 and organic solvent was removed under the reduced pressure. The crude product was purified with column chromatography (Si02; n-hexane : EtOAc = 9 : 1 ) to obtain 1 97 mg (92%, yield) of pure oily product as determined with 1 H, 11 B, 13C NMR and MS analysis. 1 H NM R (500 MHz, CDCI3, ppm) delta = 3.66 (s, 3H), 2.48 (t, J =7.6 Hz, 2H), 1 .21 (s, 12H), 0.98 (t, J = 7.5 Hz, 2H); 11 B (160 M Hz, CDCI3, ppm) delta = 33.7 (bs); 13C (125 MHz, CDCI3, ppm) delta = 175.1 , 83.2, 51 .5, 28.6, 24.8, 24.7, 24.5, 24.1 , 6.2 (broad, C-B);
92% In a dry two-necked round bottom flask were placed catalyst CuCO3 (0.03 mmol, 7.50 mg, 3 mol% according to starting material) and ligand Ph3P (0.035 mmol, 8.8 mg, 3.5 mol% according to starting material) under the nitrogen. Afterwards 2.5 mL of deionized water was added and reaction mixture was vigorously (900 rpm) stirred at ambient temperature for 20 min. The boronating reagent bis(pinacolato)diboron (1.1 mmol, 280.0 mg, 1.1 equiv.) was added in one portion and such reaction mixture was stirred at ambient temperature for 30 min. Starting material methyl acrylate (1.0 mmol) was slowly added into the reaction system and such reaction mixture was intensively stirred at 27 C for 12 hours. The reaction mixture was diluted with brine (5 mL) and extracted with EtOAc (2 x 40 mL). Combined organic layers were again washed with brine (30 mL), dried over Na2SO4 and organic solvent was removed under the reduced pressure. The crude product was purified with column chromatography (SiO2; n-hexane: EtOAc = 9: 1) to obtain 197 mg (92%, yield) of pure oily product as determined with 1H, 11B, 13C NMR and MS analysis. 1H NMR (500 MHz, CDCl3, ppm) delta = 3.66 (s, 3H), 2.48 (t, J =7.6 Hz, 2H), 1.21 (s, 12H), 0.98 (t, J = 7.5 Hz, 2H); 11B (160 MHz, CDCl3, ppm) delta = 33.7 (bs); 13C (125 MHz, CDCl3, ppm) delta = 175.1, 83.2, 51.5, 28.6, 24.8, 24.7, 24.5, 24.1, 6.2 (broad, C-B);
42% Preparation of methyl 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)propanoate A mixture of copper(I) chloride (0.172 g, 1.742 mmol), sodium tert- butoxide (0.558 g, 5.81 mmol) and bis(2-diphenylphosphino)ferrocene (0.938 g, 1.742 mmol) in THF (8 ml) was purged with N2 for 30min and stirred at room temperature for 45 min. Bis(pinacolato)diboron (16.22 g, 63.9 mmol) in THF (17ml) was added to the mixture via syringe, and the mixture stirred for another 30 min. The reaction flask was then cooled to 0C and methyl acrylate (5.0 g, 58.1 mmol) was added to the mixture by syringe followed immediately by methanol (9.40 mL, 232 mmol). The reaction was allowed to stir at room temperature overnight. The suspension was filtered through Celite and and n- hexane was added to the filtrate. A white suspension appeared which was removed by filtration and the filtrate was concentrated under vaccum. The residue was purified by Combiflash using pet ether and EtOAc (5%) as an eluant and a 40g silica column. Yield: 5.2g (42%). 1H NMR (400 MHz, CHLOROFORM- ) delta ppm 3.66 (s, 3 H) 2.43-2.48 (t, J=10 Hz, 2 H) 1.25-1.27 (s, 12 H) 1.01-1.06 (t, J=10 Hz, 2 H).
  • 3
  • 4,8-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,6,2-dioxazaborocane [ No CAS ]
  • [ 292638-85-8 ]
  • [ 1150561-77-5 ]
  • 6
  • [ 1150561-77-5 ]
  • [ 111-42-2 ]
  • [ 1290145-53-7 ]
  • 7
  • 4,8-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,6,2-dioxazaborocane [ No CAS ]
  • [ 292638-85-8 ]
  • [ 1150561-77-5 ]
  • 8
  • [ 1150561-77-5 ]
  • 6-bromo-2-(4-fluorophenyl)-5-isopropoxy-N-methylbenzofuran-3-carboxamide [ No CAS ]
  • methyl 3-(2-(4-fluorophenyl)-5-isopropoxy-3-(methylcarbamoyl)benzofuran-6-yl)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In water; toluene; at 100℃; Preparation of methyl 3-(2-(4-fluorophenyl)-5-isopropoxy-3- (methylcarbamoyl)benzofuran-6-yl)propanoate A mixture of 6-bromo-2-(4-fluorophenyl)-5-isopropoxy-N- methylbenzofuran-3-carboxamide (3.0 g, 7.38 mmol), methyl 3-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)propanoate (1.897 g, 8.86 mmol) and cesium carbonate (7.22 g, 22.15 mmol) in toluene (40 mL) and water (2 mL) at room temperature was degassed for 10 min, added with PdCl2(dppf)-CH2Cl2 adduct (0.362 g, 0.443 mmol) and then degassed again for 5 min. The resulting reaction mixture was heated at 100C for overnight. The reaction mixture was filtered through celite, the celite bed washed with EtOAc and the filtrate concentrated. The residue was purified by Combiflash using a mixture of pet ether and EtOAc as an eluent and a 120g silica gel column. The product was collected at 25% EtOAc in pet ether. Yield: 1.4g (46%). 1H NMR (400 MHz, CHLOROFORM-^) delta ppm 1.37 (d, J=6.02 Hz, 6 H) 2.62 - 2.69 (m, 2 H) 2.96 - 3.06 (m, 5 H) 3.65 - 3.69 (m, 3 H) 4.59 - 4.70 (m, 1 H) 5.76 (br. s., 1 H) 7.13 - 7.20 (m, 2 H) 7.25 - 7.30 (m, 2 H) 7.81 - 7.89 (m, 2 H). LCMS (ES+) m/z = 414.1 (M+H). Column- Acquity BEH C18 (2.1 x 50 mm) 1.7 u M phase A : 0.1% TFA in water M phase B : Acetonitrile Flow : 0.8ml/Min Time % A % 0.0 98 2 1.0 2 98 1.6 2 98 Rt min: 1.00, wavelength: 220nm
  • 9
  • [ 1150561-77-5 ]
  • 3-(tert-butyldimethylsilyloxy)-4-methoxyphenyl trifluoromethanesulfonate [ No CAS ]
  • [ 3536-96-7 ]
  • methyl 5-(3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate [ No CAS ]
  • 10
  • [ 1150561-77-5 ]
  • [ 3536-96-7 ]
  • C12H22BO4(1-) [ No CAS ]
  • 11
  • [ 768-11-6 ]
  • [ 1150561-77-5 ]
  • [ 3536-96-7 ]
  • methyl 5-(benzo[d]thiazol-5-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate [ No CAS ]
  • 12
  • [ 593-60-2 ]
  • [ 1150561-77-5 ]
  • C12H22BO4(1-) [ No CAS ]
  • 13
  • [ 1150561-77-5 ]
  • methyl (S)-5-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate [ No CAS ]
  • 14
  • [ 1150561-77-5 ]
  • methyl (S)-5-(3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate [ No CAS ]
  • 15
  • [ 1150561-77-5 ]
  • methyl (S)-5-(5-acetylthiophen-3-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate [ No CAS ]
  • 16
  • [ 1150561-77-5 ]
  • methyl (S)-5-(benzo[d]thiazol-5-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate [ No CAS ]
  • 17
  • [ 1150561-77-5 ]
  • methyl 5-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate [ No CAS ]
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