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[ CAS No. 75460-28-5 ] {[proInfo.proName]}

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Product Details of [ 75460-28-5 ]

CAS No. :75460-28-5 MDL No. :MFCD00143200
Formula : C16H23BrO6 Boiling Point : -
Linear Structure Formula :- InChI Key :XHHZIFBFFGIFNI-UHFFFAOYSA-N
M.W : 391.00 Pubchem ID :2734267
Synonyms :

Safety of [ 75460-28-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 75460-28-5 ]

* 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 [ 75460-28-5 ]

[ 75460-28-5 ] Synthesis Path-Downstream   1~24

  • 2
  • [ 75460-28-5 ]
  • [ 1079-66-9 ]
  • [ 107163-52-0 ]
YieldReaction ConditionsOperation in experiment
76% With n-butyllithium In tetrahydrofuran 1.) -90- -95 deg C; 2.) from -90 deg C to RT, 4 h;
66% With n-butyllithium; ammonium chloride; triethylamine In tetrahydrofuran at -90 - 20℃; for 4h;
  • 4
  • [ 75460-28-5 ]
  • [ 68-12-2 ]
  • [ 60835-74-7 ]
  • [ 14098-24-9 ]
  • 5
  • [ 75460-28-5 ]
  • [ 81833-15-0 ]
  • [ 306773-14-8 ]
YieldReaction ConditionsOperation in experiment
71% With piperidine; copper(l) iodide; triphenylphosphine at 80℃; for 2h;
  • 6
  • [ 89343-06-6 ]
  • [ 75460-28-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
83% With copper(l) iodide; triethylamine at 80℃;
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 80℃; 5 The acetylene-containing crown ether represented by the chemical formula 15 was synthesized as follow.[0118] First, tri(isopropyl )silylacetylene was reacted with commercially available 4’-brombenzo-18-crown 6-ether inthe presence of PdCl2(PPh3)2, copper iodide, and triethylamine at a reaction temperature of 80°C. Next, tetra butylammonium fluoride was reacted to the reactant for desilylation and the synthesis was thereby feasible.[0119] The crown ether containing intramolecularly triazapentalenes represented by the chemical formula 16 was
  • 7
  • [ 98437-23-1 ]
  • [ 75460-28-5 ]
  • [ 854520-15-3 ]
YieldReaction ConditionsOperation in experiment
73% With sodium carbonate In tetrahydrofuran; toluene at 80℃;
  • 8
  • [ 5720-05-8 ]
  • [ 75460-28-5 ]
  • [ 854520-09-5 ]
YieldReaction ConditionsOperation in experiment
76% With sodium carbonate In tetrahydrofuran; toluene at 80℃;
  • 9
  • [ 5720-07-0 ]
  • [ 75460-28-5 ]
  • [ 854520-10-8 ]
YieldReaction ConditionsOperation in experiment
76% With sodium carbonate In tetrahydrofuran; toluene at 80℃;
  • 10
  • [ 5122-94-1 ]
  • [ 75460-28-5 ]
  • [ 854520-14-2 ]
YieldReaction ConditionsOperation in experiment
65% With sodium carbonate In tetrahydrofuran; toluene at 80℃;
  • 11
  • [ 87199-17-5 ]
  • [ 75460-28-5 ]
  • [ 854520-11-9 ]
YieldReaction ConditionsOperation in experiment
77% With sodium carbonate In tetrahydrofuran; toluene at 80℃;
91 % With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 80℃; Inert atmosphere; 3.2. Synthesis of Formyl Crown Ethers 1c-e by Suzuki Coupling General procedure: General method for Suzuki coupling: In a round bottom flask under nitrogen atmosphere,40-bromobenzo-18-crown-6 ether (150 mg, 0.38 mmol) was dissolved in a mixtureof 1,2-dimethoxyethane (6 mL) and deionized water (2 mL) at room temperature andboronic acid (0.46 mmol), tetrakis(triphenylphosphine)palladium(0) (27 mg, 0.023 mmol),and potassium carbonate (315 mg, 2.28 mmol) were added. The mixture was heated at80 C for about 24 h until the disappearance of the halide (checked by TLC). After coolingto room temperature, the mixture was transferred to an extraction funnel and saturatedNaCl solution (10 mL) was added, followed by extraction with ethyl acetate (3 15 mL).The organic extracts were combined and washed with water (20 mL) and 10% aqueousNaOH (20 mL). The organic extract was dried over anhydrous magnesium sulfate, filtered,and evaporated to dryness. The crude extract was purified by column chromatographyon silica gel using dichloromethane and mixtures of increasing polarity with methanol(up to DCM/MeOH, 9:1) as the eluent. The fractions containing the pure compound werecombined and evaporated to dryness. 3.2.1. Phenylbenzocrown 1cStarting from 4-formylphenylboronic acid (69 mg, 0.46 mmol), phenylbenzocrown1c was obtained as a light brown oil (143 mg, 91%). 1H NMR (400 MHz, CDCl3): 3.63-3.77 (m, 10H, 5 CH2 ) , 3.87-3.90 (m, 2H, CH2), 3.93-3.95 (m, 2H, CH2),4.09-4.11 (m, 2H, CH2), 4.19-4.24 (m, 4H, 2 CH2), 6.93 (d, J 8.0 Hz, 1H, H60), 7.13 (d,J 2.0 Hz, 1H, H30), 7.18 (dd, J 8.2 and 2.0 Hz, 1H, H50), 7.67 (d, J 8.2 Hz, 2H, H3 and H5),7.89 (d, J 8.2 Hz, 2H, H2 and H6), 10.00 (s, 1H, CHO) ppm. 13C NMR (100.6 MHz, CDCl3): 68.65 (CH2), 68.77 (CH2), 68.83 (CH2), 68.92 (CH2), 69.16 (CH2), 69.26 (CH2), 69.30 (CH2),69.36 (CH2), 70.47 (CH2), 70.54 (CH2), 112.84 (C30), 113.62 (C60), 120.35 (C50), 127.05 (C3and C5), 130.14 (C2 and C6), 132.65 (C40), 134.65 (C1), 146.72 (C4), 148.95 (C10), 149.44 (C20),191.76 (CHO) ppm. FTIR (neat): 2916, 1659, 1630, 1594, 1456, 1347, 1253, 1123, 958, 867,799 cm1. MS (ESI) m/z (%): 417 (M++1, 62), 416 (M+, 45).
  • 12
  • [ 14047-29-1 ]
  • [ 75460-28-5 ]
  • [ 854520-13-1 ]
YieldReaction ConditionsOperation in experiment
39% With sodium carbonate In tetrahydrofuran; toluene at 80℃;
  • 13
  • [ 75460-28-5 ]
  • [ 149104-90-5 ]
  • [ 854520-12-0 ]
YieldReaction ConditionsOperation in experiment
62% With sodium carbonate In tetrahydrofuran; toluene at 80℃;
  • 14
  • [ 676-83-5 ]
  • [ 75460-28-5 ]
  • [ 865700-06-7 ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 18-bromo-2,3,5,6,8,9,11,12,14,15-decahydrobenzo[b][1,4,7,10,13,16]Hexaoxacyclotetradecene With n-butyllithium In tetrahydrofuran; hexane at -95 - -92℃; for 1.5h; Stage #2: methyldichlorophosphane In tetrahydrofuran; hexane at -90 - 20℃;
  • 15
  • [ 75460-28-5 ]
  • [ 644-97-3 ]
  • [ 865700-07-8 ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: 18-bromo-2,3,5,6,8,9,11,12,14,15-decahydrobenzo[b][1,4,7,10,13,16]Hexaoxacyclotetradecene With n-butyllithium In tetrahydrofuran; hexane at -95 - -92℃; for 1.5h; Stage #2: Dichlorophenylphosphine In tetrahydrofuran; hexane at -90 - 20℃;
  • 16
  • [ 75460-28-5 ]
  • [ 766-97-2 ]
  • [ 879874-11-0 ]
YieldReaction ConditionsOperation in experiment
60% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In various solvent(s) at 80℃; for 12h;
  • 17
  • [ 75460-28-5 ]
  • [ 100-01-6 ]
  • [ 2095155-24-9 ]
YieldReaction ConditionsOperation in experiment
90% With copper(l) iodide; caesium carbonate; <i>L</i>-proline In N,N-dimethyl-formamide at 130℃; for 168h; Inert atmosphere;
  • 18
  • [ 2257422-15-2 ]
  • [ 75460-28-5 ]
  • [ 2257422-16-3 ]
YieldReaction ConditionsOperation in experiment
222 mg With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,2-dimethoxyethane; water at 90℃; for 8h; Inert atmosphere; 1-[(3,4-benzo-18-crown-6-ether-1-yl)]-1'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ferrocene 1,1'-ferrocene diboronic acid 275 mg (1.01 mmol) and pinacol 121 mg (1.00 mmol) were dissolved in a mixed solvent of 2.24 mL of 3 M cesium carbonate aqueous solution and 6.72 mL of 1,2-dimethoxyethane (DME) and stirred for 20 minutes under nitrogen. Then 4-bromobenzo-18-crown-6-ether 400 mg (1.02 mmol) and [1,1'-bis(diphenylphosphino)ferrocene] dichloropalladium (II) 122 mg (167 mmol) were added and the solution refluxed at 90 °C for 8 hours. Completion of the reaction was indicated by thin layer chromatography (TLC) (silica gel; chloroform: methanol = 9: 1), with the appearance of a new spot (Rf = 0.6). After cooling to room temperature, the reaction solution was added to ice-water. After extraction with ethyl acetate (3 x 30 mL), the obtained organic layer was neutralized with 100 mL of ammonium chloride aqueous solution adjusted to pH 6, then washed with 100 mL of saturated sodium chloride aqueous solution and then 100 mL of distilled water. Anhydrous sodium sulfate was then added to the organic layer, the mixture filtered and the solvent removed under reduced pressure. The crude product was purified by silica gel column chromatography (gradient: chloroform only to chloroform:methanol = 98:2) to obtain a brown viscous solid (222 mg, yield 38%). 1H NMR (400 MHz, CD3CN) δ 1.33 (s, 12H, protecting group), 3.56-4.25 (m, 20H, crown ether), 4.10 (t, 2H, ferrocenyl-H), 4.24 (t, 4H, ferrocenyl-H), 4.58 (t, 2 H, ferrocenyl-H), 6.85 (d, J=8.5Hz, 1H, ph-H), 7.03 (dd, J=8.5 Hz, J=1.8 Hz, 1H, ph-H), 7.13 (d, J=1.8 Hz, 1H, ph-H). 13C NMR (100 MHz, CDCl3) δ 25.04 (protecting group), 66.82 (ferrocenyl-C), 69.11(ferrocenyl-C), 69.38-70.85 (10 carbon signals), 70.99 (ferrocenyl-C), 70.91 (ferrocenyl-C), 74.17 (ferrocenyl-C), 75.29 (ferrocenyl-C), 83.26 (protecting group), 113.30 (ph-C), 114.43 (ph-C), 119.49 (ph-C), 132.07 (ph-C), 147.79 (ph-C), 148.9 (ph-C). ESI-Mass (CH3CN, m/z), calculated for C32H43BFeO8Na [=M+Na+]: 645.22981; found: 645.22667.
  • 19
  • [ 75460-28-5 ]
  • [ 121207-31-6 ]
  • C30H39BF2N2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With palladium diacetate; potassium carbonate; triphenylphosphine; In 1,4-dioxane; at 100℃; for 15h;Sealed tube; Inert atmosphere; 1. Add 8-methyl BODIPY (0.2 mmol, 54 mg) to a 15 ml sealed bottle.with18-Bromo-2,3,5,6,8,9,11,12,14,15-decahydrobenzo[b][1,4,7,10,13,16]Hexaoxacyclotetradecene (0.24 mmol, 94 mg),Fix the sealed bottle to the thermostat mixer,Add 2ml 1,4-dioxane(about 20mmol, 1730mg),Then put a suitable magnetic stirrer in the bottle, and the tube of the argon bottle is connected to a needle.The needle is immersed, the argon valve is opened to blast the argon gas, and the dissolved oxygen and water in the solution are discharged. After 15 minutes, the argon gas is stopped and the needle is removed.Connect the argon cylinder from the side interface and purge with argon for 15 min.Subsequently, Pd(OAc) 2 (0.01 mmol, the molar ratio to the raw material BODIPY is 1:20),PPh3 (0.02 mmol) and K2CO3 (0.2 mmol). then,The mixture was stirred with heating (300 rpm) at 100 C for 15 hours.2. Next, the crude mixture is poured into CH2Cl2 (80-120 ml) to quench the reaction.It was washed three times with water (100 ml), dried over MgSO 4 and filtered.Evaporate to dryness on a rotary evaporator.Obtained by column chromatography [silica; heptane/dichloromethane; 1:2 (v/v)]It was an orange solid (41.7 mg, 37%).
  • 20
  • [ 75460-28-5 ]
  • [ 73183-34-3 ]
  • [ 2363048-23-9 ]
YieldReaction ConditionsOperation in experiment
61% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere;
61% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere; 1 Synthesis of compound 4 Add 3 (400mg, 1.03mmol) to a 50mL two-necked bottle in turn, bis(pinacolato)diboron (313mg, 1.23mmol), PdCl2(dppf) (75mg, 0.103mmol, 10%), KOAc (221mg, 2.25mmol, 3eq.), pump and ventilate three times under the protection of Ar gas, add anhydrous DMF (freeze deoxygenation) (20 mL), heat to 80°C, react for 3 hours, and stop the reaction. After cooling to room temperature, CH2Cl2 extraction (50mL×3), combine the organic phases, wash with distilled water (50mL×3), dry the organic phase with anhydrous magnesium sulfate, filter to remove magnesium sulfate, the solvent was removed by rotary evaporation, and the residue was purified with a silica gel chromatography column (eluent: dichloromethane: methanol = 20:1) to obtain a light yellow oil: 200.41 mg, with a yield of 61%.
Stage #1: 18-bromo-2,3,5,6,8,9,11,12,14,15-decahydrobenzo[b][1,4,7,10,13,16]Hexaoxacyclotetradecene With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; barium carbonate In toluene for 0.0833333h; Schlenk technique; Inert atmosphere; Stage #2: bis(pinacol)diborane In toluene at 100℃; for 15h; Schlenk technique; Inert atmosphere; Sealed tube;
  • 21
  • [ 75460-28-5 ]
  • [ 14098-24-9 ]
  • 22
  • [ 1332748-00-1 ]
  • [ 75460-28-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
80% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 80℃; for 48h; Inert atmosphere;
  • 23
  • [ 75460-28-5 ]
  • [ 4347-33-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
93 % With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 80℃; Inert atmosphere; 3.2. Synthesis of Formyl Crown Ethers 1c-e by Suzuki Coupling General procedure: General method for Suzuki coupling: In a round bottom flask under nitrogen atmosphere,40-bromobenzo-18-crown-6 ether (150 mg, 0.38 mmol) was dissolved in a mixtureof 1,2-dimethoxyethane (6 mL) and deionized water (2 mL) at room temperature andboronic acid (0.46 mmol), tetrakis(triphenylphosphine)palladium(0) (27 mg, 0.023 mmol),and potassium carbonate (315 mg, 2.28 mmol) were added. The mixture was heated at80 C for about 24 h until the disappearance of the halide (checked by TLC). After coolingto room temperature, the mixture was transferred to an extraction funnel and saturatedNaCl solution (10 mL) was added, followed by extraction with ethyl acetate (3 15 mL).The organic extracts were combined and washed with water (20 mL) and 10% aqueousNaOH (20 mL). The organic extract was dried over anhydrous magnesium sulfate, filtered,and evaporated to dryness. The crude extract was purified by column chromatographyon silica gel using dichloromethane and mixtures of increasing polarity with methanol(up to DCM/MeOH, 9:1) as the eluent. The fractions containing the pure compound werecombined and evaporated to dryness.
  • 24
  • [ 27329-70-0 ]
  • [ 75460-28-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
90 % With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 80℃; Inert atmosphere; 3.2. Synthesis of Formyl Crown Ethers 1c-e by Suzuki Coupling General procedure: General method for Suzuki coupling: In a round bottom flask under nitrogen atmosphere,40-bromobenzo-18-crown-6 ether (150 mg, 0.38 mmol) was dissolved in a mixtureof 1,2-dimethoxyethane (6 mL) and deionized water (2 mL) at room temperature andboronic acid (0.46 mmol), tetrakis(triphenylphosphine)palladium(0) (27 mg, 0.023 mmol),and potassium carbonate (315 mg, 2.28 mmol) were added. The mixture was heated at80 C for about 24 h until the disappearance of the halide (checked by TLC). After coolingto room temperature, the mixture was transferred to an extraction funnel and saturatedNaCl solution (10 mL) was added, followed by extraction with ethyl acetate (3 15 mL).The organic extracts were combined and washed with water (20 mL) and 10% aqueousNaOH (20 mL). The organic extract was dried over anhydrous magnesium sulfate, filtered,and evaporated to dryness. The crude extract was purified by column chromatographyon silica gel using dichloromethane and mixtures of increasing polarity with methanol(up to DCM/MeOH, 9:1) as the eluent. The fractions containing the pure compound werecombined and evaporated to dryness.
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