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[ CAS No. 19075-53-7 ] {[proInfo.proName]}

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Chemical Structure| 19075-53-7
Chemical Structure| 19075-53-7
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Product Details of [ 19075-53-7 ]

CAS No. :19075-53-7 MDL No. :MFCD25542199
Formula : C9H5BrOS Boiling Point : -
Linear Structure Formula :- InChI Key :PBCQAUIPFVKGOW-UHFFFAOYSA-N
M.W : 241.10 Pubchem ID :71743435
Synonyms :

Safety of [ 19075-53-7 ]

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 [ 19075-53-7 ]

* 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 [ 19075-53-7 ]

[ 19075-53-7 ] Synthesis Path-Downstream   1~27

  • 1
  • [ 19075-53-7 ]
  • [ 1660-94-2 ]
  • C18H27BrO6P2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6-bromo-benzo[b]thiophene-3-carbaldehyde; Tetraethyl methylenediphosphonate With 4-methylmorpholine N-oxide Stage #2: With lithium borohydride
  • 2
  • [ 19075-53-7 ]
  • [ 1098608-14-0 ]
YieldReaction ConditionsOperation in experiment
With pyridine; hydroxylamine hydrochloride In ethanol; water 110.b b) b) 6-Bromo-1-benzothiophene-3-carbaldehyde oxime A mixture of 6-bromo-1-benzothiophene-3-carboxaldehyde (0.76 g, 3.2 mmol) and hydroxylamine hydrochloride (0.66 g, 3.5 mmol) in water (1 mL), pyridine (6 mL) and ethanol (60 mL) was heated under reflux for 30 min. The reaction mixture was cooled and the solvent removed in vacuo. The residue was extracted from water into ethyl acetate, and the combined organic extracts washed with brine, dried (MgSO4), filtered and evaporated. The crude product was purified by flash chromatography on silica, eluding with ethyl acetate/hexane (5:95 to 100:0), to yield the title compound as a mixture of geometric isomers (trans/cis approx. 9:1).
  • 3
  • [ 19075-36-6 ]
  • [ 19075-53-7 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide In tetrachloromethane; toluene 110.a a) a) 6-Bromo-1-benzothiophene-3-carboxaldehyde To a solution of 6-bromo-3-methyl-1-benzothiophene (2.0 g, 8.8 mmol) in carbon tetrachloride (50 mL) was added N-bromosuccinimide (3.14 g, 17.6 mmol) and the mixture heated under reflux for 2.5 h while irradiating with a 1 kW flood lamp. The reaction mixture was cooled to room temperature and the solvent removed in vacuo. The residue was taken up in toluene (40 mL), silica gel (20 g) added and the mixture heated under reflux for 18 h. After cooling to room temperature, the silica was removed by filtration, washing with additional toluene and the combined organic fractions evaporated in vacuo. The crude product was purified by flash chromatography on silica, eluding with ethyl acetate/petroleum ether (0:100 to 100:0), to yield the title compound as off-white crystals.
  • 4
  • [ 57848-46-1 ]
  • [ 19075-53-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 1.2: 5.5 h / 60 °C 2.1: potassium hydroxide / water; ethanol / 1.5 h / Reflux 3.1: copper; quinoline / 2 h / 185 °C 4.1: N-Bromosuccinimide; acetic acid / chloroform / 20 °C / Cooling with ice 5.1: n-butyllithium / diethyl ether; hexane / 1.25 h / -40 °C 5.2: 4 h / -70 °C
  • 5
  • [ 19075-58-2 ]
  • [ 19075-53-7 ]
  • 6
  • [ 1426082-37-2 ]
  • [ 33513-42-7 ]
  • [ 19075-53-7 ]
YieldReaction ConditionsOperation in experiment
40% Stage #1: 3,6-dibromobenzo[b]thiophene With n-butyllithium In diethyl ether; hexane at -40℃; for 1.25h; Stage #2: N,N-dimethyl-formamide In diethyl ether; hexane at -70℃; for 4h; 4.11 6-Bromo-benzo[b]thiophene-3-carbaldehyde (26) 3,6-Dibromobenzo[b]thiophene, 25 (338 mg, 1.2 mmol) was dissolved in diethyl ether (10 mL) and cooled to -70 °C. 1.6 M n-BuLi in hexanes (0.8 mL, 1.3 mmol) was added over 35 minutes and the reaction stirred at -70 °C for a further 40 min before adding N,N-dimethylformamide (94 μl, 1.2 mmol). After stirring at -70 °C for 4 h, the reaction was quenched with 2 N HCl (6 mL), warmed to rt and the layers separated. The aqueous was extracted with diethyl ether (10 mL) and the combined organic phases were washed with saturated NaHCO3 (10 mL) and brine (5 mL) before evaporation in vacuo. The desired compound was isolated by chromatography on silica gel with 0-20% EtOAc in heptane (112 mg, 40%). 1H NMR (CDCl3), δ: 7.63 (dd, J = 8.7, 1.8, 1H, ArH), 8.01 (d, J = 1.4, 1H, ArH), 8.31 (s, 1H, ArH), 8.56 (d, J = 8.7, 1H, ArH), 10.13 (s, 1H, CHO).
  • 7
  • [ 19075-53-7 ]
  • [ 73183-34-3 ]
  • [ 1426082-56-5 ]
YieldReaction ConditionsOperation in experiment
81% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 90℃; 4.33 RRN No.135,139,141,143,144,146,148,149,151,153,...General procedures: Synthesis of 4,4,5,5-tetramethyl-1,3,2-dioxaborolane esters from aryl halides General procedure: Aryl halide (1 equiv), bis-pinacolato-diboron (1.5-3 equiv), Pd(dppf)Cl2 (0.05-0.1 equiv), and KOAc (3-6 eq.) were suspended in DMF (2-6 mL). The mixture was then heated at 90 °C for 2-6 h, cooled to rt, diluted with H2O (10 mL) and extracted with EtOAc (3 × 5 mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo. The residue was purified by chromatography using a stepped gradient of 0-10% EtOAc in heptane to yield the desired boronic ester.
  • 8
  • [ 105191-64-8 ]
  • [ 19075-53-7 ]
  • 9
  • [ 17347-32-9 ]
  • [ 19075-53-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide; acetic acid / chloroform / 20 °C / Cooling with ice 2.1: n-butyllithium / diethyl ether; hexane / 1.25 h / -40 °C 2.2: 4 h / -70 °C
  • 10
  • [ 19075-53-7 ]
  • [ 1426082-13-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 90 °C 2: potassium carbonate; triphenylphosphine; palladium diacetate / water; 1,2-dimethoxyethane / 2 h / Reflux
  • 11
  • [ 19075-53-7 ]
  • [ 1426082-14-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 90 °C 2: potassium carbonate; triphenylphosphine; palladium diacetate / water; 1,2-dimethoxyethane / 2 h / Reflux 3: sodium tetrahydroborate / ethanol / 2 h / 20 °C
  • 12
  • [ 19075-53-7 ]
  • [ 1426082-15-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 90 °C 2: tetrahydrofuran / 2 h / 0 - 20 °C 3: potassium carbonate; triphenylphosphine; palladium diacetate / water; 1,2-dimethoxyethane / 2 h / Reflux
  • 13
  • [ 19075-53-7 ]
  • [ 1426082-38-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 90 °C 2: tetrahydrofuran / 2 h / 0 - 20 °C
  • 14
  • [ 19075-53-7 ]
  • [ 619-45-4 ]
  • 6-bromo-3-[(4-methoxycarbonylphenyl)aminomethyl]benzothiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: 6-bromo-benzo[b]thiophene-3-carbaldehyde; 4-methoxycarbonyl aniline With acetic acid In ethanol for 1h; Reflux; Stage #2: With sodium cyanoborohydride In ethanol at 0 - 20℃; for 1h;
  • 15
  • [ 5381-20-4 ]
  • [ 19075-53-7 ]
YieldReaction ConditionsOperation in experiment
40% With bromine; In acetonitrile; at 20℃; for 18h; Synthesis of 6-bromobenzothiophene-3-carbaldehyde 915Benzothiophene-3-carbaldehyde (81 1 mg, 5 mmol, 1 equiv) 3a was dissolved in acetonitrile (15 ml.) and to this solution was slowly added bromine (1 ,29 ml_, 25 mmol, 5 equiv). The resulting reaction mixture was stirred at room temperature for 18 hour after which it was partitioned between an aqueous sodium bicarbonate solution (50 ml.) and EtOAc (50 ml_). To this biphasic solution was added dropwise, under vigorous stirring, a saturated aqueous sodium thiosulfate solution until discoloration of the organic medium. The organic layer was separated, and the aqueous layer was extracted with EtOAc (25 ml_). The organic fractions were combined, dried (MgS04), filtered and concentrated under vacuum. Purification through column chromatography (Rf0.14, EtOAc/PE: 1/13) yielded 6-bromobenzothiophene-3- carbaldehyde 9 (482 mg, 2 mmol, 40%) as a white powder. 9: 6-bromobenzothiophene-3-carbaldehyde 40% as white powder; Rf0.14 (EtOAc/PE: 1/13); m.p 1 1 1 C;1H-NMR (400 MHz, CDCI3): delta = 7.63 (dd, J = 8.7, 1.7 Hz, 1 H); 8.04 (d, J = 1.7 Hz, 1 H); 8.30 (s, 1 H); 8.56 (d, J = 8.7 Hz, 1 H); 10.12 (s, 1 H);13C-NMR (100.6 MHz, CDCIs): delta = 120.2, 125.0, 125.9, 129.6, 134.0, 136.1 , 141.8, 143.2 and 185.1 ; IR (cm"1): v = 1662 (C=0); Elemental Analysis Calcd (%) for C9H5BrOS: C 44.84 H 2.09; Found: C 45.17 H 1.71 .
2.2 g With N-Bromosuccinimide; In tetrachloromethane; at 20℃; for 2h;Irradiation; Compound 43 (1.62 g, 10 mmol) was weighed.N-bromosuccinimide (1.78 g, 10 mmol) was added to a three-necked flask and 20 mL of carbon tetrachloride was added.Irradiate with a 200w incandescent bulb and react at room temperature for 2 hours. Filter out the white solid,Concentrate the liquid. 2.2 g (92%) of a colorless transparent liquid were obtained.
  • 16
  • [ 19075-53-7 ]
  • 3-[(4-methoxycarbonylphenyl)aminomethyl]-6-phenylbenzothiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / ethanol; toluene; water / 8 h / Reflux 2.1: acetic acid / ethanol / 1 h / Reflux 2.2: 1 h / 0 - 20 °C
  • 17
  • [ 19075-53-7 ]
  • 6-bromo-3-[N-benzyl-N-(4-methoxycarbonylphenyl)aminomethyl]benzothiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: acetic acid / ethanol / 1 h / Reflux 1.2: 1 h / 0 - 20 °C 2.1: sodium hydride; potassium iodide / N,N-dimethyl-formamide / 2.5 h / 20 °C / Inert atmosphere
  • 18
  • [ 19075-53-7 ]
  • 3-[N-benzyl-N-(4-methoxycarbonylphenyl)aminomethyl]-6-phenylbenzothiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / ethanol; toluene; water / 8 h / Reflux 2.1: acetic acid / ethanol / 1 h / Reflux 2.2: 1 h / 0 - 20 °C 3.1: sodium hydride; potassium iodide / N,N-dimethyl-formamide / 2.5 h / 20 °C / Inert atmosphere
  • 19
  • [ 19075-53-7 ]
  • 6-bromo-3-[(4-hydroxycarbamoylphenyl)aminomethyl]benzothiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: acetic acid / ethanol / 1 h / Reflux 1.2: 1 h / 0 - 20 °C 2.1: hydroxylamine; potassium hydroxide / water; tetrahydrofuran / 0.17 h / 20 °C
  • 20
  • [ 19075-53-7 ]
  • 3-[(4-hydroxycarbamoylphenyl)aminomethyl]-6-phenylbenzothiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / ethanol; toluene; water / 8 h / Reflux 2.1: acetic acid / ethanol / 1 h / Reflux 2.2: 1 h / 0 - 20 °C 3.1: hydroxylamine; potassium hydroxide / water; tetrahydrofuran / 0.17 h / 20 °C
  • 21
  • [ 19075-53-7 ]
  • 6-bromo-3-[N-benzyl-N-(4-hydroxycarbamoylphenyl)aminomethyl]benzothiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: acetic acid / ethanol / 1 h / Reflux 1.2: 1 h / 0 - 20 °C 2.1: sodium hydride; potassium iodide / N,N-dimethyl-formamide / 2.5 h / 20 °C / Inert atmosphere 3.1: hydroxylamine; potassium hydroxide / water; tetrahydrofuran / 0.17 h / 20 °C
  • 22
  • [ 19075-53-7 ]
  • 3-[N-benzyl-N-(4-hydroxycarbamoylphenyl)aminomethyl]-6-phenylbenzothiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / ethanol; toluene; water / 8 h / Reflux 2.1: acetic acid / ethanol / 1 h / Reflux 2.2: 1 h / 0 - 20 °C 3.1: sodium hydride; potassium iodide / N,N-dimethyl-formamide / 2.5 h / 20 °C / Inert atmosphere 4.1: hydroxylamine; potassium hydroxide / water; tetrahydrofuran / 0.17 h / 20 °C
  • 23
  • [ 19075-53-7 ]
  • [ 98-80-6 ]
  • 6-phenylbenzothiophene-3-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 8h; Reflux;
  • 24
  • [ 95-15-8 ]
  • [ 19075-53-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / tetrachloromethane / 2 h / 20 °C / Irradiation 2: n-butyllithium / dichloromethane / 3 h / -78 - 20 °C 3: N-Bromosuccinimide / tetrachloromethane / 2 h / 20 °C / Irradiation
  • 25
  • [ 19075-53-7 ]
  • [ 51114-94-4 ]
  • (E)-4-(6-bromobenzo[b]thiophen-3-y1)but-3-enoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
2-carboxyethyltriphenylphosphonium bromide (4.57 g, 11 mmol) was weighed into a three-necked flask.Dissolve, reduce the reaction system to minus 30 ° C, add potassium t-butoxide (1.23 g, 11 mmol),After reacting for 30 minutes, compound 44 (2.41 g, 10 mmol) was added, and the mixture was reacted at room temperature for 3 hours.The reaction was quenched by the addition of water (50 mL).The organic phase is then washed with water and the organic phase is washed with saturated sodium chloride. Dry over anhydrous sodium sulfate, filter and concentrate.1.4 g (47percent) of a yellow solid were obtained.The crude product was used in the next step without purification.
  • 26
  • [ 7342-82-7 ]
  • [ 19075-53-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / dichloromethane / 3 h / -78 - 20 °C 2: N-Bromosuccinimide / tetrachloromethane / 2 h / 20 °C / Irradiation
  • 27
  • [ 19075-53-7 ]
  • 7-bromodibenzo[b,d]thiophen-4(3Η)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium <i>tert</i>-butylate / 0.5 h / -30 °C 1.2: 3 h / 20 °C 2.1: polyphosphoric acid / 2 h / 80 °C
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