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[ CAS No. 19693-10-8 ] {[proInfo.proName]}

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Chemical Structure| 19693-10-8
Chemical Structure| 19693-10-8
Structure of 19693-10-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 19693-10-8 ]

CAS No. :19693-10-8 MDL No. :MFCD12026197
Formula : C7H7BrS Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :203.10 Pubchem ID :-
Synonyms :

Safety of [ 19693-10-8 ]

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Application In Synthesis of [ 19693-10-8 ]

* 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 [ 19693-10-8 ]

[ 19693-10-8 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 5465-65-6 ]
  • [ 19693-10-8 ]
  • [ 13799-06-9 ]
YieldReaction ConditionsOperation in experiment
With potassium ethoxide In isopropyl alcohol Heating;
  • 2
  • [ 53078-85-6 ]
  • [ 19693-10-8 ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: 2-bromo-5-methylaniline With hydrogenchloride; sodium nitrite In water at -10 - -5℃; for 1.16667h; Stage #2: With potassium ethyl xanthogenate In water at 60℃; for 0.833333h; Stage #3: With potassium hydroxide In ethanol for 18h; Reflux; 1.A Step A: Preparation of 2-bromo-5-methylbenzenethiol To a suspension of 2-bromo-5-methylaniline (9.76 g, 52.5 mmol) in 8 mL of water was added 8.8 mL of concentrated HCl. The reaction mixture was cooled in an ice/NaCl bath (approximately -5 to -10 °C). Approximately 8 g of ice was added to the reaction mixture. A solution of NaNO2 (3.60 g, 52.3 mmol) in 16.2 mL of water was added slowly over 40 minutes. The solution was then stirred for an additional 30 minutes with cooling. Separately, a solution of potassium ethyl xanthogenate (10.1 g, 63.0 mmol) in 54 mL of water was prepared and heated to 60 °C. The cold solution of diazonium salt was then added slowly over 20 minutes to the solution of potassium ethyl xanthogenate. The reaction mixture was stirred for an additional 30 minutes at 60 °C, and then cooled to ambient temperature. It was then poured into a saturated aqueous NaHCO3 solution and extracted three times with dichloromethane. The combined organic extracts were washed with saturated brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. To this residue was added a solution of 1.8 M KOH/EtOH, and the reaction mixture was heated to reflux for 18 hours. The reaction mixture was then cooled to ambient temperature and concentrated in vacuo. The residue was dissolved in water and extracted with diethyl ether. The aqueous phase was then acidified with concentrated HCl and extracted three times with dichloromethane. The combined organic extracts were dried over anhydrous MgSO4, filtered, concentrated, and purified by silica gel chromatography using 0-5% ethyl acetate/hexanes as eluent to provide 8.26 g (78%) of the title Compound as a pale yellow oil. 1H NMR (500 MHz, CDCl3( ^ ggd: 2.25-2.28 (m, 3H) 3.96 (s, 1H) 6.81 (d, J=8.03 Hz, 1H) 7.18 (d, J=1.89 Hz, 1H) 7.40 (d, J=8.20 Hz, 1H).
Multistep reaction;
YieldReaction ConditionsOperation in experiment
Rk. mit 4-Chlor-3-nitro-acetophenon -> 6-Brom-2'-nitro-3-methyl-4'-acetyl-diphenylsulfid;
  • 4
  • [ 19693-10-8 ]
  • C18H18INO2 [ No CAS ]
  • ethyl 8-methyl-1-phenylpyrrolo[3,2,1-kl]phenothiazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: C18H18INO2 With N-Bromosuccinimide; iodine; potassium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: 2-bromo-5-methylbenzenethiol With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; <i>L</i>-proline In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere; Schlenk technique;
  • 5
  • [ 19693-10-8 ]
  • C18H18INO2 [ No CAS ]
  • ethyl 4,8-dimethyl-1-phenylpyrrolo[3,2,1-kl]phenothiazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: C18H18INO2 With N-Bromosuccinimide; iodine; potassium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: 2-bromo-5-methylbenzenethiol With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; <i>L</i>-proline In N,N-dimethyl-formamide at 120℃; for 20h; Inert atmosphere; Schlenk technique;
  • 6
  • [ 19693-10-8 ]
  • [ 10282-57-2 ]
  • 7-methyl-10-phenyldibenzo[b,f][1,4]thiazepin-11(10H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(l) iodide; N,N`-dimethylethylenediamine; potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 12 h / 100 °C / Inert atmosphere; Schlenk technique 2: N,N-dimethyl-formamide / 36 h / 140 °C / Inert atmosphere; Schlenk technique
  • 7
  • [ 19693-10-8 ]
  • [ 10282-57-2 ]
  • C20H16BrNOS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; potassium <i>tert</i>-butylate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 100℃; for 12h; Inert atmosphere; Schlenk technique; chemoselective reaction; General Procedure for Synthesis of Dibenzothiazepinone General procedure: A Schlenk tubewas charged with N-substituted 2-bromobenzamide (0.25 mmol), CuI (5.0 mg,0.025 mmol), N,N-dimethylglycine hydrochloride (7.0 mg, 0.05 mmol), andCs2CO3 (163.0 mg, 0.5 mmol). The tube was evacuated and backfilled with argonbefore 2-bromothiophenol derivatives (0.375 mmol) and 1.0 mL DMF was added.The reaction mixture was stirred at 80 °C for 12 h (or 100 °C for 11n), andfurther elevated temperature to 120 °C for 36 h. After the reaction mixture wascooled to room temperature, 5 mL of saturated NH4Cl solution was added. Themixture was extracted with EtOAc and the organic layer was washed with water,brine and dried over Na2SO4. After concentration in vacuo, the residue waspurified by column chromatography on silica gel to provide the desired products.
  • 8
  • [ 19693-10-8 ]
  • [ 2032-35-1 ]
  • 7-bromo-4-methylbenzo[b]thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% Stage #1: 2-bromo-5-methylbenzenethiol; Bromoacetaldehyde diethyl acetal With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h; Inert atmosphere; Stage #2: In toluene at 100℃; for 1h; Inert atmosphere; 1.B Step B: Preparation of 7-bromo-4-methylbenzo[b]thiophene A dry round bottomed flask was charged with 2-bromo-5-methylbenzenethiol (8.25 g, 40.6 mmol) and K2CO3 (16.8 g, 122 mmol), and purged with nitrogen gas. Anhydrous DMF (200 mL) was added followed by bromoacetaldehyde diethyl acetal (7.33 mL, 48.7 mmol), and the mixture was heated to 60 °C for 4 hours. The reaction mixture was then cooled to ambient temperature and quenched with a saturated NH4Cl solution. It was extracted three times with ethyl acetate. The combined organic extracts were washed with saturated brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. This residue was added to a round bottomed flask and purged with nitrogen gas. Toluene (90 mL) was added, followed by PPA (20.2 g, 114 mmol). The reaction mixture was heated to 100 °C for 1 hour, and then cooled to ambient temperature. The reaction mixture was then poured into water and extracted three times with ethyl acetate. The combined organic extracts were dried over anhydrous MgSO4, filtered, concentrated, and was purified by silica gel chromatography using 0-4% ethyl acetate/hexanes as eluent to provide 1.73 g (19%) of the title Compound as a pale yellow oil. NMR (500 MHz, CDCl3( ^ ggd: 2.58 (d, J=0.63 Hz, 3H) 7.03-7.07 (m, 1H) 7.38 (s, 1H) 7.48-7.53 (m, 2H).
  • 9
  • [ 19693-10-8 ]
  • 7-bromo-4-(dibromomethyl)benzo[b]thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 60 °C / Inert atmosphere 1.2: polyphosphoric acid / 1 h / 100 °C / Inert atmosphere 2.1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 18 h / Inert atmosphere; Reflux
  • 10
  • [ 19693-10-8 ]
  • 7-bromobenzo[b]thiophene-4-carboxaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 60 °C / Inert atmosphere 1.2: polyphosphoric acid / 1 h / 100 °C / Inert atmosphere 2.1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 18 h / Inert atmosphere; Reflux 3.1: silver nitrate; water / ethanol / Reflux
  • 11
  • [ 19693-10-8 ]
  • 3-(7-bromobenzo[b]thien-4-yl)-5-(3,5-dichloro-4-fluorophenyl)-4,5-dihydro-5-(trifluoromethyl)isoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 60 °C / Inert atmosphere 1.2: polyphosphoric acid / 1 h / 100 °C / Inert atmosphere 2.1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 18 h / Inert atmosphere; Reflux 3.1: silver nitrate; water / ethanol / Reflux 4.1: hydroxylamine / water; ethanol / 18 h / 20 °C 4.2: 2.5 h / 20 °C / Inert atmosphere 4.3: 72 h / 20 °C
  • 12
  • [ 19693-10-8 ]
  • 4-[5-(3,5-dichloro-4-fluorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]benzo[b]thiophene-7-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 60 °C / Inert atmosphere 1.2: polyphosphoric acid / 1 h / 100 °C / Inert atmosphere 2.1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 18 h / Inert atmosphere; Reflux 3.1: silver nitrate; water / ethanol / Reflux 4.1: hydroxylamine / water; ethanol / 18 h / 20 °C 4.2: 2.5 h / 20 °C / Inert atmosphere 4.3: 72 h / 20 °C 5.1: triethylamine; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; methanol / 18 h / Reflux 5.2: 7 h / 50 - 65 °C
  • 13
  • [ 19693-10-8 ]
  • 4-[5-(3,5-dichloro-4-fluorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyrimidinylmethyl)benzo[b]thiophene-7-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 60 °C / Inert atmosphere 1.2: polyphosphoric acid / 1 h / 100 °C / Inert atmosphere 2.1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 18 h / Inert atmosphere; Reflux 3.1: silver nitrate; water / ethanol / Reflux 4.1: hydroxylamine / water; ethanol / 18 h / 20 °C 4.2: 2.5 h / 20 °C / Inert atmosphere 4.3: 72 h / 20 °C 5.1: triethylamine; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; methanol / 18 h / Reflux 5.2: 7 h / 50 - 65 °C 6.1: HATU; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.08 h / 20 °C 6.2: 2 h / 20 °C
  • 14
  • [ 75-15-0 ]
  • [ 19693-10-8 ]
  • 2-mercaptocinnamic acid [ No CAS ]
  • 9-methyl-5,11-dithiabenzo[a]fluorene-6-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With sodium ethanolate; platinum(II) chloride In acetonitrile at 80℃; for 8h; 2 Preparation of 4b product At room temperature, add 5mmol 2-mercaptocinnamic acid, 6mmol carbon disulfide and 5mmol 2-bromo-5-methylthiophenol in a 25mL round bottom flask, and then add 15mL acetonitrile, 0.5mmol platinum chloride and With 10 mmol sodium ethoxide, the reaction was stirred at 80°C for 8 hours.After cooling, add 20mL saturated sodium chloride aqueous solution to the system, extract 3 times with ethyl acetate, 20mL each time, combine the organic phases, dry with anhydrous sodium sulfate, evaporate the solvent, 200-300 mesh silica gel column chromatography Dithiocoumarin and benzothiophenes 4b(1356mg, 91% yield, yellow powder).The 4b1H NMR spectrum is shown in Figure 3, and the 13C NMR spectrum is shown in Figure 4.
  • 15
  • [ 75-15-0 ]
  • [ 19693-10-8 ]
  • 2-mercapto-4-methoxycinnamic acid [ No CAS ]
  • 3-methoxy-9-methyl-5,11-dithiabenzo[a]fluorene-6-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With sodium ethanolate; platinum(II) chloride In acetonitrile at 80℃; for 8h; 7 Preparation of 4g product At room temperature, add 5mmol 2-mercapto-4-methoxycinnamic acid, 6mmol of carbon disulfide, and 5mmol of 2-bromo-5-methylthiophenol to a 25mL round bottom flask, and then add 15mL of acetonitrile,With 0.5 mmol platinum chloride and 10 mmol sodium ethoxide, the reaction was stirred at 80°C for 8 hours.After cooling, add 20mL saturated sodium chloride aqueous solution to the system, extract 3 times with ethyl acetate, 20mL each time, combine the organic phases, dry with anhydrous sodium sulfate, evaporate the solvent, 200-300 mesh silica gel column chromatography 4 g of dithiocoumarin benzothiophene compound (1508 mg, yield 92%, yellow powder).The 4g1HNMR spectrum is shown in Figure 13, and the 13C NMR spectrum is shown in Figure 14.
  • 16
  • [ 452-74-4 ]
  • [ 19693-10-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C 2: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C
  • 17
  • (2-bromo-5-methylphenyl)(4-methoxybenzyl)sulfane [ No CAS ]
  • [ 19693-10-8 ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 2h; 2.2B.2B.12 To a solution of (2-bromo-5-methylphenyl)(4-methoxybenzyl)sulfane (2, 18.0 g, 55.90 mmol) in dichloromethane (140 mL) is added a mixture of trifluoroacetic acid (20 mL) and triflic acid (5 mL) in dichloromethane (40 mL) at 0 °C drop wise and the reaction mixture is stirred at room temperature for 2 h. After completion, the reaction is poured into ice-water and extracted with dichloromethane. The organic layer is washed with water, brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to get the crude product 2-bromo-5- methylbenzenethiol (3).
  • 18
  • [ 19693-10-8 ]
  • 7-bromo-4-methylbenzo[b]thiophene-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 0.17 h / 20 °C 1.2: 5 h / 20 °C 2.1: sulfuric acid / dichloromethane / 5 h / 20 °C
  • 19
  • [ 19693-10-8 ]
  • methyl 7-bromo-4-methylbenzo[b]thiophene-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 0.17 h / 20 °C 1.2: 5 h / 20 °C 2.1: sulfuric acid / dichloromethane / 5 h / 20 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C
  • 20
  • [ 1113-59-3 ]
  • [ 19693-10-8 ]
  • 3-((2-bromo-5-methylphenyl)thio)-2-oxopropanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-bromo-5-methylbenzenethiol With potassium carbonate In acetone at 20℃; for 0.166667h; Stage #2: bromopyruvic acid In acetone at 20℃; for 5h; 2.2B.2B.12 To a solution 2-bromo-5-methylbenzenethiol (3, 4.7 g, 23.27 mmol) in acetone (47.0 mL) is added potassium carbonate (16.0 g, 116.35 mmol) at room temperature and the mixture is stirred for 10 min.3-Bromo-2-oxopropanoic acid (3a, 11.6 g, 69.80 mmol) is added to the reaction mixture and stirred for 5 h at room temperature. After completion, the acetone is evaporated under reduced pressure; the residue is diluted with water and extracted with ethyl acetate. The organic layer is washed with water, brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to get 3-((2-bromo-5-methylphenyl)thio)-2-oxopropanoic acid (4).
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