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Product Details of [ 62932-94-9 ]

CAS No. :62932-94-9 MDL No. :MFCD18976157
Formula : C9H9BrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :XWRBIXFTHXFQKC-UHFFFAOYSA-N
M.W : 245.07 Pubchem ID :11334055
Synonyms :

Safety of [ 62932-94-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501 UN#:3261
Hazard Statements:H314 Packing Group:
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Application In Synthesis of [ 62932-94-9 ]

* 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 [ 62932-94-9 ]

[ 62932-94-9 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 116-11-0 ]
  • [ 62932-94-9 ]
  • [ 102293-80-1 ]
YieldReaction ConditionsOperation in experiment
100% With toluene-4-sulfonic acid In dichloromethane at 0℃; for 0.666667h;
With resin-SO3H In dichloromethane
With toluene-4-sulfonic acid In tetrahydrofuran at -10 - 10℃; for 1h; 1 Example 1: Preparation of Compound 3 [0039] 0.5 kg of compound 2 (solution 1) and 2.5 g p-Toluenesulfonic acid (solution 2) were added into 4 L of THF (tetrahydrofuran) at a temperature of -10 to 10 °C to form a reaction solution. 0.36 kg of 2-methoxypropene solution was then added dropwise into the reaction solution. The reaction solution was set for 1 hour to complete the reaction to obtainthe compound 3 solution.
  • 2
  • [ 24085-07-2 ]
  • [ 62932-94-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogen bromide; In methanol; water; Reference Example 3 2-Bromo-1-(2,2-dimethylbenzo[1,2-d]-1,3-dioxan-6-yl)-1-ethanone <strong>[24085-07-2]2-Acetoxymethyl-4-bromoacetylphenyl acetate</strong> (18.6 g) was dissolved in 90 ml of methanol, 100 ml of 47% hydrobromic acid was added with stirring under ice-cooling, and the mixture was subjected to 16 hours of reaction at room temperature. Water was added to the reaction solution with stirring under ice-cooling, and the resulting precipitates were collected by filtration and washed with water and hexane to give 9.54 g of 2-bromo-4'-hydroxy-3'-hydroxymethylacetophenone having a melting point of 117 to 119 C. IR (KBr): 3440, 1677 cm-1; 1 H-NMR (DMSO-d6); delta ppm: 4.50 (2H, s), 4.75 (2H, s), 5.10 (1H, br s), 6.87 (1H, d, J=8.5 Hz), 7.79 (1H, dd, J=8.5, 2.4 Hz), 7.99 (1H, d, J=2.4 Hz), 10.52 (1H, s)
With hydrogen bromide; In methanol; water; REFERENCE EXAMPLE 1 2-Bromo-1-(2,2-dimethylbenzo[1,2-d]-1,3-dioxan-6-yl)-1-ethanone <strong>[24085-07-2]2-Acetoxymethyl-4-bromoacetylphenyl acetate</strong> (18.6 g) was dissolved in methanol (90 ml), and 47% hydrobromic acid (100 ml) was added to the solution under ice-cooling with stirring. After reaction for 16 hours at room temperature, water was added to the reaction mixture under ice-cooling with stirring, and the precipitates were collected by filtration and washed with water and hexane to give 2-bromo-4'-hydroxy-3'-hydroxymethylacetophenone (9.54 g) having a melting point of 117-119 C. IR (KBr): 3440, 1677 cm-1 1 H-NMR (DMSO-d6) delta ppm: 4.50 (2H, s), 4.75 (2H, s), 5.10 (1H, br s), 6.87 (1H, d, J=8.5 Hz), 7.79 (1H, dd, J=8.5, 2.4 Hz), 7.99 (1H, d, J=2.4 Hz), 10.52 (1H, s)
  • 3
  • [ 24085-06-1 ]
  • [ 62932-94-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: polyvinylpyridinium bromide perbromide resin / CH2Cl2 2: 1N HBr / tetrahydrofuran / 75 °C
  • 4
  • [ 99-93-4 ]
  • [ 62932-94-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: resin-bound piperazinomethylpolystyrene / H2O; tetrahydrofuran 1.2: 14 percent / pTSA / toluene / 110 °C 2.1: polyvinylpyridinium bromide perbromide resin / CH2Cl2 3.1: 1N HBr / tetrahydrofuran / 75 °C
  • 5
  • [ 62932-94-9 ]
  • (R)-(-)-salmeterol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: resin-SO3H / CH2Cl2 2.1: resin-N(iPr)2 / tetrahydrofuran 3.1: CaCl2 / methanol / 0.17 h / 0 °C 3.2: 76 percent / resin-NMe3(1+)*BH4(1-) / methanol / 2 h / 0 - 20 °C 4.1: (polystyrylmethyl)trimethylammonium cyanoborohydride; AcOH / CH2Cl2 4.2: 98 percent / resin-NMe3(1+)*NaCO3(1-) / CH2Cl2 5.1: H2 / Pd(OH)2/C / ethyl acetate / 2 h 5.2: 87 percent / SCX-2
  • 6
  • [ 62932-94-9 ]
  • [ 380414-67-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: resin-SO3H / CH2Cl2 2: resin-N(iPr)2 / tetrahydrofuran
  • 7
  • [ 62932-94-9 ]
  • [ 380414-68-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: resin-SO3H / CH2Cl2 2.1: resin-N(iPr)2 / tetrahydrofuran 3.1: CaCl2 / methanol / 0.17 h / 0 °C 3.2: 76 percent / resin-NMe3(1+)*BH4(1-) / methanol / 2 h / 0 - 20 °C
  • 8
  • [ 62932-94-9 ]
  • [ 380414-69-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: resin-SO3H / CH2Cl2 2.1: resin-N(iPr)2 / tetrahydrofuran 3.1: CaCl2 / methanol / 0.17 h / 0 °C 3.2: 76 percent / resin-NMe3(1+)*BH4(1-) / methanol / 2 h / 0 - 20 °C 4.1: (polystyrylmethyl)trimethylammonium cyanoborohydride; AcOH / CH2Cl2 4.2: 98 percent / resin-NMe3(1+)*NaCO3(1-) / CH2Cl2
  • 9
  • [ 62932-94-9 ]
  • 2-{bis-[6-(4-phenyl-butoxy)-hexyl]-amino}-1-(2,2-dimethyl-4<i>H</i>-benzo[1,3]dioxin-6-yl)-ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: resin-SO3H / CH2Cl2 2.1: resin-N(iPr)2 / tetrahydrofuran 3.1: CaCl2 / methanol / 0.17 h / 0 °C 3.2: 76 percent / resin-NMe3(1+)*BH4(1-) / methanol / 2 h / 0 - 20 °C 4.1: H2 / Pd(OH)2/C / ethyl acetate
  • 10
  • [ 62932-94-9 ]
  • [ 384340-07-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 100 percent / TsOH*H2O / CH2Cl2 / 0.67 h / 0 °C 2: 95 percent / NaN3 / dimethylformamide / 2 h / 20 °C 3: 94 percent / Pichia angusta / acetonitrile / 48 h / 28 °C 4: 86 percent / H2 / Pd/C / ethanol / 3 h
Multi-step reaction with 4 steps 1: 100 percent / TsOH*H2O / CH2Cl2 / 0.67 h / 0 °C 2: 95 percent / NaN3 / dimethylformamide / 2 h / 20 °C 3: Mucor racemosus / 42 h 4: 86 percent / H2 / Pd/C / ethanol / 3 h
  • 11
  • [ 62932-94-9 ]
  • [ 384340-05-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 100 percent / TsOH*H2O / CH2Cl2 / 0.67 h / 0 °C 2: 95 percent / NaN3 / dimethylformamide / 2 h / 20 °C
  • 12
  • [ 62932-94-9 ]
  • [ 384340-06-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 100 percent / TsOH*H2O / CH2Cl2 / 0.67 h / 0 °C 2: 95 percent / NaN3 / dimethylformamide / 2 h / 20 °C 3: 94 percent / Pichia angusta / acetonitrile / 48 h / 28 °C
Multi-step reaction with 3 steps 1: 100 percent / TsOH*H2O / CH2Cl2 / 0.67 h / 0 °C 2: 95 percent / NaN3 / dimethylformamide / 2 h / 20 °C 3: Mucor racemosus / 42 h
  • 13
  • [ 62932-94-9 ]
  • [ 384340-09-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 100 percent / TsOH*H2O / CH2Cl2 / 0.67 h / 0 °C 2: 95 percent / NaN3 / dimethylformamide / 2 h / 20 °C 3: Mucor racemosus / 42 h
  • 14
  • [ 62932-94-9 ]
  • [ 384340-08-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 100 percent / TsOH*H2O / CH2Cl2 / 0.67 h / 0 °C 2: 95 percent / NaN3 / dimethylformamide / 2 h / 20 °C 3: 94 percent / Pichia angusta / acetonitrile / 48 h / 28 °C 4: 86 percent / H2 / Pd/C / ethanol / 3 h 5: 70 percent / dimethylformamide / 67 h / 20 °C
Multi-step reaction with 5 steps 1: 100 percent / TsOH*H2O / CH2Cl2 / 0.67 h / 0 °C 2: 95 percent / NaN3 / dimethylformamide / 2 h / 20 °C 3: Mucor racemosus / 42 h 4: 86 percent / H2 / Pd/C / ethanol / 3 h 5: 70 percent / dimethylformamide / 67 h / 20 °C
  • 15
  • [ 62932-94-9 ]
  • (S)-salmeterol acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 100 percent / TsOH*H2O / CH2Cl2 / 0.67 h / 0 °C 2: 95 percent / NaN3 / dimethylformamide / 2 h / 20 °C 3: 94 percent / Pichia angusta / acetonitrile / 48 h / 28 °C 4: 86 percent / H2 / Pd/C / ethanol / 3 h 5: 70 percent / dimethylformamide / 67 h / 20 °C 6: 100 percent / H2O / 0.5 h / 71 °C
Multi-step reaction with 6 steps 1: 100 percent / TsOH*H2O / CH2Cl2 / 0.67 h / 0 °C 2: 95 percent / NaN3 / dimethylformamide / 2 h / 20 °C 3: Mucor racemosus / 42 h 4: 86 percent / H2 / Pd/C / ethanol / 3 h 5: 70 percent / dimethylformamide / 67 h / 20 °C 6: 100 percent / H2O / 0.5 h / 71 °C
  • 16
  • [ 62932-94-9 ]
  • 2-{bis-[6-(4-phenyl-butoxy)-hexyl]-amino}-1-(2,2-dimethyl-4<i>H</i>-benzo[1,3]dioxin-6-yl)-ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 100 percent / TsOH*H2O / CH2Cl2 / 0.67 h / 0 °C 2: 95 percent / NaN3 / dimethylformamide / 2 h / 20 °C 3: 94 percent / Pichia angusta / acetonitrile / 48 h / 28 °C 4: 86 percent / H2 / Pd/C / ethanol / 3 h 5: dimethylformamide / 67 h / 20 °C
Multi-step reaction with 5 steps 1: 100 percent / TsOH*H2O / CH2Cl2 / 0.67 h / 0 °C 2: 95 percent / NaN3 / dimethylformamide / 2 h / 20 °C 3: Mucor racemosus / 42 h 4: 86 percent / H2 / Pd/C / ethanol / 3 h 5: dimethylformamide / 67 h / 20 °C
  • 17
  • [ 115787-50-3 ]
  • [ 62932-94-9 ]
YieldReaction ConditionsOperation in experiment
94% Add <strong>[115787-50-3]5-bromoacetyl-2-hydroxybenzaldehyde</strong> (200g) to a 5L three-necked flask, add propionic acid (500mL), tetrahydrofuran (1.5L), start stirring, cool down to 5-10 C, within a half hour, a small amount Add sodium borohydride (21.8g) in portions, add in the liquid phase, control the raw material, less than 1% of the raw materials, add 1L of water to the reaction system, stir at 0-5 C for 1 hour, filter, wash with 500 mL of water, and dry. The white solid was obtained in 190 g, the yield was 94%, the purity was 97.3%, and the over-reduced product was 1.9%.
88% With sodium tetrahydroborate; acetic acid; at 0 - 20℃;Inert atmosphere; Dissolve 12 g of 5- (bromoacetyl) salicylaldehyde in 50 mL of acetic acid, then cool to 0 C and add 2.3 g of sodium borohydride under nitrogen. After adding slowly warming to room temperature, stirring was continued until the reaction was complete. The pH of the reaction solution was adjusted to neutrality at 0 C with saturated aqueous sodium carbonate solution, then 100 mL of distilled water was added and the mixture was back-extracted three times with ethyl acetate. The organic phases were combined, the organic phase was washed with distilled water and brine, dried over anhydrous sodium sulfate, filtered, concentrated and dried in vacuo to give the crude product as a red oil. The crude product was purified by column chromatography (n-pentane:ethyl acetate 9: 1-2: 8) to give 10.6 g of 2-bromo-1-(4-hydroxy-3-(hydroxymethyl)phenyl)ethanone as pale yellow solid with a yield of 88%.
  • 18
  • [ 77-76-9 ]
  • [ 62932-94-9 ]
  • [ 102293-80-1 ]
YieldReaction ConditionsOperation in experiment
99% With toluene-4-sulfonic acid In dichloromethane
93.7% With toluene-4-sulfonic acid In propan-2-one at 30℃; for 2h; 1; 6; 11 Embodiment 11, the preparation of formula VI compoundv 1000.0g of compound VII, 1481.65g of 2,2-dimethoxypropane, 7.75g of p-toluenesulfonic acid, and 5000ml of acetone were successively added to a 20L reactor, reacted at 30°C for 2h, added with 12000ml of water, a solid was precipitated, and the temperature dropped to 0 -5°C, kept stirring for 1 hour, filtered; the filter cake was dried at 60°C for 12 hours to obtain 1090.5 g of compound VI with a yield of 93.7%.
84% With toluene-4-sulfonic acid In dichloromethane at 20℃; 3 Example 3 Synthesis of 2-bromo-1-(2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)ethanone 10 g of 2-bromo-1-(4-hydroxy-3-(hydroxymethyl)phenyl)ethanone obtained in Example 2 and 0.14 g of a catalytic amount of p-toluenesulfonic acid were added to a 250 mL three necked flask . Then, 100 mL of dichloromethane was added to stir to form a pale yellow suspension, and a solution of 8.5 g of 2,2-dimethoxypropane and 40 mL of dichloromethane was slowly added dropwise to the reaction solution at room temperature. Continue stirring the reaction until the reaction solution becomes clear, add saturated potassium bicarbonate solution to the reaction solution to adjust the reaction system to weakly alkaline. The layers were separated and the organic layer was separated. The organic phase was washed with saturated aqueous sodium chloride solution and water, respectively, and then dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration, concentrated and dried in vacuo to give a pale yellow oily liquid, 9.8 g, yield 84%.
82% In dichloromethane at 20℃; for 10h;
174.01 g With toluene-4-sulfonic acid In dichloromethane at 20℃; for 2h; 2 Example 2 Synthesis of Compound C (6-bromoacetyl-2,2-dimethyl-4H- benzo [1,3] dioxin) (1) Weigh 150.06g of Compound B (5-(2-bromoacetyl)-2-hydroxybenzyl alcohol), add 1.5L of dichloromethane, stirred and dispersed at room temperature, added 1.16g of p-toluenesulfonic acid monohydrate; weighed 128.87g of 2,2-dimethoxypropane, drip added to the reaction system, room temperature reaction for 2h;(2) HPLC, TLC monitoring to the reaction complete, add 0.75L purified water, adjust the pH to 7~8 with saturated potassium bicarbonate solution, stand and stratify, collect the lower organic phase, and then wash the organic phase with 0.75L of purified water once; the organic phase is added to the anhydrous sodium sulfate, except for water;(3) Filtration, a small amount of dichloromethane wash filter residue, concentrated under reduced pressure to 174.01g of oil, as compound C (6-bromoacetyl-2,2-dimethyl-4H-benzo[1,3]dioxin), directly used in the next step of the reaction, do not calculate the yield

  • 19
  • [ 90-02-8 ]
  • [ 62932-94-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 15 h / Reflux 2: sodium tetrahydroborate; acetic acid / 1 h / 10 °C
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / dichloromethane / 0.5 h / 50 °C 1.2: 12 h / 40 °C 2.1: sodium tetrahydroborate; acetic acid / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / dichloromethane / 0.5 h / 10 - 30 °C 1.2: 24 h / 35 °C 2.1: acetic acid; sodium tetrahydroborate / 1 h / 25 °C
  • 20
  • [ 62932-94-9 ]
  • [ 1424337-27-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dichloromethane / 10 h / 20 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C 4: triethylamine / N,N-dimethyl-formamide / 24 h / 65 °C
  • 21
  • [ 62932-94-9 ]
  • [ 1424337-28-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dichloromethane / 10 h / 20 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C 4: triethylamine / N,N-dimethyl-formamide / 24 h / 65 °C
  • 22
  • [ 62932-94-9 ]
  • [ 1424337-29-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dichloromethane / 10 h / 20 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C 4: triethylamine / N,N-dimethyl-formamide / 24 h / 65 °C
  • 23
  • [ 62932-94-9 ]
  • [ 1424337-30-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dichloromethane / 10 h / 20 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C 4: triethylamine / N,N-dimethyl-formamide / 24 h / 65 °C
  • 24
  • [ 62932-94-9 ]
  • C28H31Cl2N3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: dichloromethane / 10 h / 20 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C 4: triethylamine / N,N-dimethyl-formamide / 24 h / 65 °C 5: ammonium fluoride / water; ethanol / 48 h / 45 °C
  • 25
  • [ 62932-94-9 ]
  • C29H33Cl2N3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: dichloromethane / 10 h / 20 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C 4: triethylamine / N,N-dimethyl-formamide / 24 h / 65 °C 5: ammonium fluoride / water; ethanol / 48 h / 45 °C
  • 26
  • [ 62932-94-9 ]
  • C30H35Cl2N3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: dichloromethane / 10 h / 20 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C 4: triethylamine / N,N-dimethyl-formamide / 24 h / 65 °C 5: ammonium fluoride / water; ethanol / 48 h / 45 °C
  • 27
  • [ 62932-94-9 ]
  • C31H37Cl2N3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: dichloromethane / 10 h / 20 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C 4: triethylamine / N,N-dimethyl-formamide / 24 h / 65 °C 5: ammonium fluoride / water; ethanol / 48 h / 45 °C
  • 28
  • [ 62932-94-9 ]
  • [ 1424337-09-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: dichloromethane / 10 h / 20 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C 4: triethylamine / N,N-dimethyl-formamide / 24 h / 65 °C 5: ammonium fluoride / water; ethanol / 48 h / 45 °C 6: hydrogenchloride / water; ethanol / 12 h / 20 °C
  • 29
  • [ 62932-94-9 ]
  • [ 1424337-10-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: dichloromethane / 10 h / 20 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C 4: triethylamine / N,N-dimethyl-formamide / 24 h / 65 °C 5: ammonium fluoride / water; ethanol / 48 h / 45 °C 6: hydrogenchloride / water; ethanol / 12 h / 20 °C
  • 30
  • [ 62932-94-9 ]
  • [ 1424337-11-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: dichloromethane / 10 h / 20 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C 4: triethylamine / N,N-dimethyl-formamide / 24 h / 65 °C 5: ammonium fluoride / water; ethanol / 48 h / 45 °C 6: hydrogenchloride / water; ethanol / 12 h / 20 °C
  • 31
  • [ 62932-94-9 ]
  • [ 1424337-12-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: dichloromethane / 10 h / 20 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C 4: triethylamine / N,N-dimethyl-formamide / 24 h / 65 °C 5: ammonium fluoride / water; ethanol / 48 h / 45 °C 6: hydrogenchloride / water; ethanol / 12 h / 20 °C
  • 32
  • [ 62932-94-9 ]
  • [ 956234-46-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloromethane / 10 h / 20 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C
  • 33
  • [ 62932-94-9 ]
  • [ 956234-47-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dichloromethane / 10 h / 20 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C
  • 34
  • [ 62932-94-9 ]
  • cis-2-(3-(benzyl(2-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)-2-oxoethyl)amino)propyl)-4-(3,4-dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydrophthalazin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloromethane / 10 h / 20 °C 2: triethylamine / dichloromethane / 12 h / 20 °C
  • 35
  • [ 62932-94-9 ]
  • 2-(4-(benzyl(2-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)-2-oxoethyl)amino)butyl)-4-(3,4-dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydrophthalazin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloromethane / 10 h / 20 °C 2: triethylamine / dichloromethane / 12 h / 20 °C
  • 36
  • [ 62932-94-9 ]
  • 2-(5-(benzyl(2-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)-2-oxoethyl)amino)pentyl)-4-(3,4-dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydrophthalazin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloromethane / 10 h / 20 °C 2: triethylamine / dichloromethane / 12 h / 20 °C
  • 37
  • [ 84244-65-5 ]
  • [ 62932-94-9 ]
  • C17H27NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
600 mg Stage #1: 2-bromo-1-[4-hydroxy-3-(hydroxymethyl)-phenyl]ethanone With toluene-4-sulfonic acid; 2,2-dimethoxy-propane In dichloromethane at 0 - 20℃; Stage #2: With sodium tetrahydroborate In methanol at 0 - 5℃; for 2h; Stage #3: 6-amino-6-methylheptanoic acid Further stages; 1 Example 1, Immunogen and coating antigen preparation I. Preparation of the hapten Example 1, Immunogen and coating antigen preparation I. Preparation of the hapten 1, the intermediate sal-1 synthesis:250ml three necked flask was added 2-bromo-1- [4-hydroxy-3- (hydroxymethyl) phenyl]ethan-1-one 1000mg,Dichloromethane 200ml, 3.8mg of p-toluenesulfonic acid, the ice bath was cooled to 0-5 °C, was added dropwise 2,2-dimethoxypropane 2208ul, overnight at room temperature, TLC the reaction was complete after-treatment, the organic solution was washed with saturated aqueous sodium bicarbonate phase was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give an off-white solid 1211mg (sal-1). 2, intermediate sal-2 synthesis:100ml three-necked flaskIntermediate sal-1, 1140mg, anhydrous methanol 40ml, cooled to 0 °C ice bath, and sodium borohydride 227mg, 0-5 degrees C for 2 hours, TLC the reaction was complete after-treatment, the reaction solution was poured into ice water, two dichloromethane extraction, the organic phase with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give an off-white solid 1018mg (sal-2). 3, intermediate sal-3 synthesis:100mlthree-necked flask was added Intermediate sal-2,1000mg, anhydrous methanol 40ml, cooled to 0 °C ice bath was added anhydrous potassium carbonate 1396mg, room temperature for 2 hours, the reaction was complete after TLC, filtered, washed with methanol, filtered 5ml cake, and the filtrate concentrated under reduced pressure to give an oily object 700mg (sal-3). 4, intermediate sal-4 Synthesis: 100ml three-necked flask was added Intermediate sal-3,700mg, anhydrous methanol 40ml, triethylamine 686mg, 6- amino-6-methyl-1-heptanoic acid 540mg, .the reaction was refluxed for 12 hours, TLC the reaction was complete after-treatment,Methanol was distilled off under reduced pressure, the residue was dissolved in dichloromethane, washed with water, saturated aqueous sodium chloride The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give an oil 1008mg (sal-4). 5, hapten sal-5 synthesis:100mlthree-necked flask was added Intermediate sal-4,1000mg, anhydrous methanol 40ml, ice bath cooling to 0-5 °, was added dropwise 10ml 1M sulfuric acid at room temperature for 2 hours,After completion of the reaction by TLC treatment, methanol was distilled off under reduced pressure, cooled to 10 degrees precipitated white solid was filtered, the filter cake was washed with a small amount of water, and dried to give a white solid 600mg (sal-5), the dry matter obtained is hapten.
  • 38
  • [ 3235-46-9 ]
  • [ 62932-94-9 ]
  • 4-[2-(4-hydroxy-3-(hydroxymethyl)phenyl)-2-oxoethyl]amino}-4-methylpentanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium methylate at 20℃; Cooling with ice; 1.S1 Oriented Synthesis of Salbutamol Derivatives: 2-bromo-1- [4-hydroxy-3- (hydroxymethyl) phenyl] -ethan-1-one (CAS: 62932-94-9)(0.02 mol) of 4-amino-4-methyl-pentanoic acid (imported brand) was added to a 50 ml three-necked flask and 20 ml of saturated sodium methoxide was added as a solvent under ice- After the reaction at room temperature for 1-2h, crystallization, filtration, washing and drying to obtain a white solid, namely:4 - [2- (4-hydroxy-3- (hydroxymethyl) phenyl) -2-oxoethyl] amino} -4-methylpentanoic acid.
  • 39
  • [ 6045-08-5 ]
  • [ 62932-94-9 ]
  • salbutamol-D<SUB>9</SUB> [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.365 g Stage #1: 1,1,1,3,3,3-hexadeuterio-2-(trideuteriomethyl)propan-2-amine; 2-bromo-1-[4-hydroxy-3-(hydroxymethyl)-phenyl]ethanone With tetrabutylammomium bromide In chloroform at 60℃; for 4h; Stage #2: With sodium tetrahydroborate In chloroform at 20℃; for 4h; 6.B B, Stable Isotope Labeled Salbutamol - D9 Synthesis B, Stable Isotope Labeled Salbutamol - D9 SynthesisIn a 100 mL flask equipped with a thermometer and a condenser tube, 2.451 g (0.01 mol) was added1- (4-hydroxy-3-hydroxymethylphenyl) -2-bromoethanone, chloroform (40 mL) and an appropriate amount of tetrabutylammonium bromide under stirring2.40 g (0.03 mol) of t-butylamine-D9, and the reaction temperature was controlled at 60 ° C for 4 h. After completion of the reaction, the reaction mixture was added1.135 g (0.03 mol) of NaBH4 as the reducing agent, and the reaction was continued for 4 h at room temperature. Washed with water, recrystallized and dried to give 1.365 gStable isotope labeled salbutamol-D9, with tert-butylamine-D9 as 55.4%, chromatographic purity greater than 99.0%, isotopeAbundance greater than 98.7atom% D.
  • 40
  • [ 62932-94-9 ]
  • 6-((R)-hydroxy-2-(tert-butylamino)ethyl)-2,2-dimethyl-4H-benzo[1,3]dioxin D-(+)-dibenzoyltartaric acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / dichloromethane / 20 °C 2: potassium carbonate / tetrahydrofuran; lithium hydroxide monohydrate 3: sodium tetrahydridoborate; methanol / 0 - 20 °C / Inert atmosphere 4: methanol; ethanol / 1 h / 40 °C
Multi-step reaction with 5 steps 1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C 2: (1R,2S)-(+)-cis-1-amino-2-indanol; borane-N,N-diethylaniline complex / tetrahydrofuran / 3.5 h / 5 °C / Inert atmosphere 3: potassium carbonate / methanol / 1 h / 20 °C 4: potassium carbonate / ethanol / 16 h / 50 °C 5: methanol; isopropanol / 2 h / 50 °C
  • 41
  • [ 62932-94-9 ]
  • 2-azido-1-(4-hydroxy-3-(hydroxymethyl)phenyl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium azide In N,N-dimethyl-formamide at 20℃; for 24h;
With sodium azide In N,N-dimethyl-formamide at 20℃; for 12h; 1.1 Example 1.1 Preparation of compound 1 Add 2-bromo-1-[4-hydroxy-3-(hydroxymethyl)phenyl]ethan-1-one (4g, 16.3218mmol) and NaN3 (1.53g, 23.6mmol) into the reaction flask, add N,N-dimethylformamide (DMF); After reacting the reaction system with stirring at room temperature for 12 hours, recrystallize to obtain 2.1168 g of raw material azide intermediate. Add the above intermediate (500mg, 2.41mmol), N,N-diisopropylethylamine (DIPEA, 1.0495 mL, 6.025mmol) and 4-dimethylaminopyridine (DMAP, 29.9mg, 0.241mmol) into the reaction flask. Add ultra-dry acetonitrile, cool to -20 °C and add carbon tetrachloride (2.32mL, 24.1mmol) and diethyl phosphite (5, diethyl phosphite, 357μL, 2.77mmol) dropwise;After dripping, the reaction solution was transferred to room temperature and stirred for 1 hour. The solvent was spin-dried and the solvent was added to dichloromethane to dissolve, washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated, and quickly separated and purified by silica gel column chromatography to obtain compound 1 (521mg , 63%).
  • 42
  • [ 62932-94-9 ]
  • 4-(2-azidoacetyl)-2-(hydroxymethyl)phenyl diethyl phosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 24 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; dmap; tetrachloromethane / acetonitrile / 1 h / -20 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 12 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; dmap / acetonitrile; tetrachloromethane / 1 h / -20 - 20 °C
  • 43
  • [ 62932-94-9 ]
  • C13H16N3O6P [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium azide / N,N-dimethyl-formamide / 24 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; dmap; tetrachloromethane / acetonitrile / 1 h / -20 - 20 °C / Inert atmosphere 3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C
Multi-step reaction with 3 steps 1: sodium azide / N,N-dimethyl-formamide / 12 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; dmap / acetonitrile; tetrachloromethane / 1 h / -20 - 20 °C 3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C
  • 44
  • [ 62932-94-9 ]
  • 4-(2-azidoacetyl)-2-(difluoromethyl)phenyl diethyl phosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium azide / N,N-dimethyl-formamide / 24 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; dmap; tetrachloromethane / acetonitrile / 1 h / -20 - 20 °C / Inert atmosphere 3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 4: diethylamino-sulfur trifluoride / dichloromethane / 2 h / 0 °C
Multi-step reaction with 4 steps 1: sodium azide / N,N-dimethyl-formamide / 12 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; dmap / acetonitrile; tetrachloromethane / 1 h / -20 - 20 °C 3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 4: diethylamino-sulfur trifluoride / dichloromethane / 2 h / Cooling
  • 45
  • [ 62932-94-9 ]
  • 2-azido-1-{4-[(diethoxyphosphoryl)oxy]-3-(difluoromethyl)-phenyl}ethyl ethylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium azide / N,N-dimethyl-formamide / 24 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; dmap; tetrachloromethane / acetonitrile / 1 h / -20 - 20 °C / Inert atmosphere 3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 4: diethylamino-sulfur trifluoride / dichloromethane / 2 h / 0 °C 5: sodium tetrahydroborate / methanol / 0.5 h / 0 °C 6: triethylamine / dichloromethane / 12 h / Reflux; Inert atmosphere
Multi-step reaction with 6 steps 1: sodium azide / N,N-dimethyl-formamide / 12 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; dmap / acetonitrile; tetrachloromethane / 1 h / -20 - 20 °C 3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 4: diethylamino-sulfur trifluoride / dichloromethane / 2 h / Cooling 5: sodium tetrahydroborate; methanol / 0.5 h / Cooling 6: triethylamine / dichloromethane / 12 h / Reflux
  • 46
  • [ 62932-94-9 ]
  • C13H18F2N3O5P [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium azide / N,N-dimethyl-formamide / 24 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; dmap; tetrachloromethane / acetonitrile / 1 h / -20 - 20 °C / Inert atmosphere 3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 4: diethylamino-sulfur trifluoride / dichloromethane / 2 h / 0 °C 5: sodium tetrahydroborate / methanol / 0.5 h / 0 °C
Multi-step reaction with 5 steps 1: sodium azide / N,N-dimethyl-formamide / 12 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; dmap / acetonitrile; tetrachloromethane / 1 h / -20 - 20 °C 3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 4: diethylamino-sulfur trifluoride / dichloromethane / 2 h / Cooling 5: sodium tetrahydroborate; methanol / 0.5 h / Cooling
  • 47
  • [ 62932-94-9 ]
  • 2-Azido-1-[3-(difluoromethyl)-4-(phosphonooxy)phenyl]ethyl ethylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: sodium azide / N,N-dimethyl-formamide / 24 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; dmap; tetrachloromethane / acetonitrile / 1 h / -20 - 20 °C / Inert atmosphere 3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 4: diethylamino-sulfur trifluoride / dichloromethane / 2 h / 0 °C 5: sodium tetrahydroborate / methanol / 0.5 h / 0 °C 6: triethylamine / dichloromethane / 12 h / Reflux; Inert atmosphere 7: acetonitrile / 12 h / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 7 steps 1: sodium azide / N,N-dimethyl-formamide / 12 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; dmap / acetonitrile; tetrachloromethane / 1 h / -20 - 20 °C 3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 4: diethylamino-sulfur trifluoride / dichloromethane / 2 h / Cooling 5: sodium tetrahydroborate; methanol / 0.5 h / Cooling 6: triethylamine / dichloromethane / 12 h / Reflux 7: trimethylsilyl bromide / acetonitrile / 12 h / 20 °C / Inert atmosphere
  • 48
  • [ 116-11-0 ]
  • [ 3378-72-1 ]
  • [ 62932-94-9 ]
  • C23H29NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 2-Methoxypropene; 2-bromo-1-[4-hydroxy-3-(hydroxymethyl)-phenyl]ethanone With toluene-4-sulfonic acid In acetone at 0 - 5℃; for 1h; Stage #2: N-tert-butylbenzylamine In acetone at 55℃; for 22h; 3 (3) Synthesis of Intermediate III During the reaction, 18 g of Intermediate II was added to the reaction flask, 90 g of acetone and 0.09 g of p-toluenesulfonic acid were added, and the temperature was lowered. 13.4 g of 2-methoxypropene was added dropwise at 0-5°C. The temperature is controlled at 0-5°C, the dripping is completed, the reaction is kept for 1 hour, and monitored by TLC. Add 26.25 g of N-benzyl tert-butylamine. The temperature was raised to 55°C. The reaction was performed for 22 hours, monitored by TLC. Cool down to 25°C and stir for 10-20Min, filter with suction, and concentrate the filtrate. Evaporate to dryness to obtain an oily substance, add 180mL ethyl acetate/n-hexane (1:20), 20.2g silica gel, heat up to 55°C, and stir for 1h. Suction filtration, add the filter cake to the reaction flask, add 180mL ethyl acetate/n-hexane (1:20) and heat to 55, stir for 30min, filter with suction, add the filter cake to the reaction flask, add 90mL ethyl acetate/n-hexane The alkane (1:20) was stirred for 30 min, filtered with suction, and the filtrate was combined and concentrated to dryness at 45° C. to obtain a solid. Add 72g of methanol and stir and raise the temperature to 55°C until all the solids are dissolved, then lower the temperature to 20°C and stir for 1h. The temperature was lowered to 0-5°C, stirred for 4h, and filtered with suction. The filter cake was rinsed with 15mL methanol at 0-5°C, and the product was dried under vacuum at 45°C. The yield is 70%-80%.
  • 49
  • [ 62932-94-9 ]
  • [ 238762-31-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / propan-2-one / 2 h / 30 °C 2.1: dimethylsulfide borane complex; (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole / tetrahydrofuran / 1 h / 5 - 20 °C 3.1: potassium carbonate / isopropanol / 3 h / 60 °C 4.1: ethanol / 3 h / 75 °C 4.2: 20 °C 5.1: anhydrous sodium carbonate / ethyl acetate / 20 °C
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C 2: (1R,2S)-(+)-cis-1-amino-2-indanol; borane-N,N-diethylaniline complex / tetrahydrofuran / 3.5 h / 5 °C / Inert atmosphere 3: potassium carbonate / methanol / 1 h / 20 °C 4: potassium carbonate / ethanol / 16 h / 50 °C
  • 50
  • [ 62932-94-9 ]
  • levalbuterol hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: toluene-4-sulfonic acid / propan-2-one / 2 h / 30 °C 2.1: dimethylsulfide borane complex; (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole / tetrahydrofuran / 1 h / 5 - 20 °C 3.1: potassium carbonate / isopropanol / 3 h / 60 °C 4.1: ethanol / 3 h / 75 °C 4.2: 20 °C 5.1: anhydrous sodium carbonate / ethyl acetate / 20 °C 6.1: hydrogenchloride / ethyl acetate; lithium hydroxide monohydrate / 2 h / 0 - 5 °C
Multi-step reaction with 6 steps 1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C 2: (1R,2S)-(+)-cis-1-amino-2-indanol; borane-N,N-diethylaniline complex / tetrahydrofuran / 3.5 h / 5 °C / Inert atmosphere 3: potassium carbonate / methanol / 1 h / 20 °C 4: potassium carbonate / ethanol / 16 h / 50 °C 5: methanol; isopropanol / 2 h / 50 °C 6: hydrogenchloride / methanol; tert-butyl methyl ether; ethyl acetate / 5 h / 20 °C / Inert atmosphere
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