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Chemical Structure| 870778-88-4 Chemical Structure| 870778-88-4

Structure of 870778-88-4

Chemical Structure| 870778-88-4

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Product Details of [ 870778-88-4 ]

CAS No. :870778-88-4
Formula : C10H15BO4
M.W : 210.04
SMILES Code : COC1=C(B(O)O)C(OC(C)C)=CC=C1
MDL No. :MFCD07369736
InChI Key :ZAKDYROLNHVOEL-UHFFFAOYSA-N
Pubchem ID :16217894

Safety of [ 870778-88-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501

Application In Synthesis of [ 870778-88-4 ]

* 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.

  • Downstream synthetic route of [ 870778-88-4 ]

[ 870778-88-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 90-11-9 ]
  • [ 870778-88-4 ]
  • [ 1246888-95-8 ]
  • 2
  • [ 4805-22-5 ]
  • [ 870778-88-4 ]
  • [ 1415917-11-1 ]
YieldReaction ConditionsOperation in experiment
84.1% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; toluene; at 110℃; for 8h;Inert atmosphere; In a 50-mL reaction container, 326.3 mg (1.01 mmol) of XX-4 (2, 5-dibromobithiophene) and 749.8 mg (3.57 mmol) of 2-isopropoxy-6-methoxyphenylboronic acid were mixed in a toluene/tetrahydrofuran (4 mL/4 mL) solvent mixture, and dissolved oxygen was removed by nitrogen. [0119] Subsequently, 5.9 mg (0.026 mmol) of Pd(OAc)2, 21.4 mg (0.052 mmol) of 2-dicyclohexylphosphino-2 ', 6'- dimethoxybiphenyl (S-Phos), and 1123.7 mg (4.88 mmol) of tripotassxum phosphate were added to the mixture under a nitrogen atmosphere, followed by heating to reflux at 110C for 8 hours. [0120] The reaction solution was cooled to room temperature, concentrated under reduced pressure, and subjected to silica gel chromatography (mobile phase: hexane/chloroform = 1/3) for isolation and purification to give compound B-l (418.8 mg, yield: 84.1%) as a white solid powder . [0121] As in Example 1, the structure of compound B-l was confirmed by NMR and MALDI-MS . Specifically, 494 as M+ of this compound was confirmed by MALDI-MS. The measurement results of NMR are shown below: 1NMR (CDCl3) σ (ppm) : 7.48 (d,2H), 7.18 (t,2H), 7.17 (d,2H), 6.65 (d,2H), 6.62 (d,2H), 4.58 (sept,2H), 3.87 (s,6H), 1.36 (s, 12H) . 13C-NMR (CDCl3) σ (ppm): 158.12, 156.14, 137.72, 133.35, 130.02, 128.42, 122.49, 114.24, 107.88, 104.54, 71.88, 56.27, 22.46.
84.1% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; toluene; at 110℃; for 8h;Inert atmosphere; <Synthesis Example 7: Synthesis of Exemplified Compound B-7>0149] In a 50-ml reaction vessel, XX-7 (2,5-dibromobithiophene) (326.3 mg, 1.01 mmol) and 2-isopropoxy-6-methoxyphenylboronic acid (749.8 mg, 3.57 mmol) were mixed in a toluene/tetrahydrofuran (4 ml/4 ml) mixed solvent. Dissolved oxygen was removed by nitrogen. [0150] Next, Pd(OAc)2 (5.9 mg, 0.026 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos) (21.4 mg, 0.052 mmol), and tripotassium phosphate (1123.7 mg, 4.88 mmol) were added thereto in a nitrogen atmosphere. The mixture was then heated and refluxed at 110C to perform a reaction for 8 hours. [0151] The reaction solution was cooled to room temperature and then concentrated under reduced pressure. Separation and purification were performed by silica-gel chromatography (mobile phase: hexane/chloroform = 1/3) to give a white solid power B-7 (418.8 mg, yield: 84.1%). Measurement by MALDl-MS demonstrated that M+ of this compound was found to be 494.2.
  • 3
  • [ 870778-88-4 ]
  • [ 174508-31-7 ]
  • [ 1415917-07-5 ]
YieldReaction ConditionsOperation in experiment
54% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; toluene; at 110℃; for 7h;Inert atmosphere; In a 50-mL reaction container, 500 mg (1.67 mmol) of XX-2 (2, 5-dibromo-ethylenedioxythiophene) and 1.05 g (5.0 mmol) of 2-isopropoxy-6-methoxyphenylboronic acid were mixed in a toluene/tetrahydrofuran (10 mL/5 mL) solvent mixture, and dissolved oxygen was removed by nitrogen. Subsequently, 19 mg (0.083 mmol) of Pd(0Ac)2, 89 mg (0.22 mmol) of 2- dicyclohexylphosphino-2', 6 ' -dimethoxybiphenyl (S-Phos) , and 1.92 g (8.35 mmol) of tripotassium phosphate were added to the mixture under a nitrogen atmosphere, followed by heating to reflux at 110C for 7 hours. The reaction solution was cooled to room temperature, concentrated under reduced pressure, and subjected to silica gel chromatography (mobile phase: hexane/ethyl acetate = 4/3) for isolation and purification to give compound A-ll (420 mg, yield: 54%) as a white solid powder. [0112] As in Example 1, the structure of compound A-ll was confirmed by NMR and MALDI-MS. Specifically, 470 as M+ of this compound was confirmed by MALDI-MS. The measurement results of NMR are shown below: 1H-NMR (CDCl3) (ppm) : 7.21 (t,2H), 6.63 (d,2H), 6.60 (d,2H), 4.41 (m,2H), 4.20 (s,4H), 3.81 (s,6H), 1.25 (s,6H), 1.24 (s, 6H) . 13C-NMR (CDCl3) sigma (ppm): 159.01, 157.52, 138.10, 129.20, 112.07, 108.96, 108.36, 104.53, 71.80, 64.49, 56.06, 22.23
54% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; toluene; at 110℃; for 7h;Inert atmosphere; <Synthesis Example 6: Synthesis of Exemplified Compound B-6>0145] In a 50-ml reaction vessel, XX-6 (2,5-dibromoethylenedioxythiophene) (500 mg, 1.67 mmol) and 2-isopropoxy-6-methoxyphenylboronic acid (1.05 g, 5.0 mmol) were mixed in a toluene/tetrahydrofuran (10 ml/5 ml) mixed solvent. Dissolved oxygen was removed by nitrogen. [0146] Next, Pd(OAc)2 (19 mg, 0.083 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos) (89 mg, 0.22 mmol), and tripotassium phosphate (1.92 g, 8.35 mmol) were added thereto in a nitrogen atmosphere. The mixture was then heated and refluxed at 110C to perform a reaction for 7 hours. [0147] The reaction solution was cooled to room temperature and then concentrated under reduced pressure. Separation and purification were performed by silica-gel chromatography (mobile phase: hexane/ethyl acetate = 4/3) to give a white solid power B-6 (420 mg, yield: 54%). Measurement by MALDl-MS demonstrated that M+ of this compound was found to be 470.
54% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; toluene; at 110℃; for 7h;Inert atmosphere; With a 50-ml reaction container, XX-9(2,5-dibromoethylene dioxythiophene):500mg (1.67mmol), 2-isopropoxy 6-methoxy phenylboronic acid: 1.05 g (5.0mmol) was mixed in toluene / tetrahydrofuran (10-ml/five ml) mixed solvent, and nitrogen removed dissolved oxygen.Next, Pd(OAc) 2:19mg (0.083mmol), 2-dicyclohexyl phosphino 2',6'-dimethoxybiphenyl (S-Phos): 89 mg (0.22mmol) and phosphoric-acid 3 potassium posphate: 1.92 g (8.35mmol) was added under a nitrogen atmosphere, and it heated at reflux at 110 degrees C, and performed the reaction for 7 hours. The reaction solution was concentrated in vacuum after cooling to the room temperature, separation refinement was carried out with silica gel chromatography (mobile phase: hexane/ethyl acetate =4/3), and D-6 of white solid powder was obtained (420 mg, 54% of yield).
 

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